# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Sethuraman Sankararaman'
_publ_contact_author_email       SANKA@IITM.AC.IN

_publ_section_title              
;
Hydrogen-bond network in isomeric phenylene
dipropynoic acids and their DABCO salts. Water mediated helical hydrogen
bond motifs
;
loop_
_publ_author_name
'Sethuraman Sankararaman'
'Rajendran Saravanakumar'
'Babu Varghese'

# Attachment '12PPAnew.cif'

#===========================================================================
data_12ppa
_database_code_depnum_ccdc_archive 'CCDC 656598'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H6 O4'
_chemical_formula_sum            'C12 H6 O4'
_chemical_formula_weight         214.17

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2/c
_symmetry_space_group_name_Hall  '-P 2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   3.7990(3)
_cell_length_b                   10.4652(9)
_cell_length_c                   12.4395(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.309(6)
_cell_angle_gamma                90.00
_cell_volume                     494.55(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2445
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.5

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8643
_exptl_absorpt_correction_T_max  0.9332
_exptl_absorpt_process_details   'SADABS(Bruker, 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5954
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         26.40
_reflns_number_total             1016
_reflns_number_gt                761
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare etal., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP 32 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.
The C-H hydrogens were fixed at chemically idealised positions and were
given riding model refinement with C-H (0.930Å)and Uiso1.2 time Ueq
of parent atom. The differnece map showed hydroxyl hydrogens disordered
to both oxygens. Each hydrogen was assigned 50% occupancy.
One of them (of O1) was restrained to ride over the parent oxygen
(O-H 0.82Å and C-O-H tetrahedral)and its isotropic thermal parameter
was refined. The other hydrogen was given unrestrained isotropic
refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0302P)²+0.9194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1016
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1736
_refine_ls_wR_factor_gt          0.1602
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_restrained_S_all      1.191
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7144(10) 0.6544(3) 0.5955(3) 0.0447(9) Uani 1 1 d . . .
C2 C 0.7758(10) 0.7859(4) 0.6206(3) 0.0449(9) Uani 1 1 d . . .
C3 C 0.8350(9) 0.8913(3) 0.6512(3) 0.0402(8) Uani 1 1 d . . .
C4 C 0.9178(8) 1.0120(3) 0.6988(3) 0.0361(8) Uani 1 1 d . . .
C5 C 0.8400(9) 1.1274(3) 0.6491(3) 0.0432(9) Uani 1 1 d . . .
H5 H 0.7339 1.1281 0.5815 0.052 Uiso 1 1 calc R . .
C6 C 0.9207(10) 1.2419(3) 0.7002(3) 0.0491(10) Uani 1 1 d . . .
H6 H 0.8672 1.3191 0.6667 0.059 Uiso 1 1 calc R . .
O1 O 0.5450(8) 0.6261(3) 0.5119(2) 0.0590(9) Uani 1 1 d . . .
H1 H 0.5237 0.5482 0.5080 0.07(3) Uiso 0.50 1 calc PR . .
O2 O 0.8279(10) 0.5680(3) 0.6583(3) 0.0700(11) Uani 1 1 d . . .
H2 H 0.98(3) 0.580(8) 0.703(6) 0.06(3) Uiso 0.50 1 d P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.052(2) 0.041(2) 0.0408(19) -0.0035(16) -0.0127(17) -0.0030(16)
C2 0.051(2) 0.044(2) 0.0394(19) -0.0027(16) -0.0096(16) -0.0009(17)
C3 0.0412(19) 0.0406(19) 0.0388(18) -0.0037(15) -0.0036(14) -0.0018(15)
C4 0.0377(17) 0.0335(18) 0.0370(17) -0.0014(14) -0.0018(14) 0.0007(14)
C5 0.049(2) 0.042(2) 0.0379(18) 0.0013(16) -0.0089(15) 0.0002(17)
C6 0.061(2) 0.0303(19) 0.056(2) 0.0058(16) -0.0075(18) 0.0042(16)
O1 0.085(2) 0.0431(17) 0.0484(16) -0.0042(12) -0.0347(14) -0.0055(14)
O2 0.103(3) 0.0475(17) 0.0589(19) 0.0081(15) -0.0421(19) -0.0080(17)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.256(4) . ?
C1 O2 1.269(4) . ?
C1 C2 1.430(5) . ?
C2 C3 1.188(5) . ?
C3 C4 1.430(5) . ?
C4 C5 1.388(5) . ?
C4 C4 1.415(6) 2_756 ?
C5 C6 1.390(5) . ?
C5 H5 0.9300 . ?
C6 C6 1.375(7) 2_756 ?
C6 H6 0.9300 . ?
O1 H1 0.8200 . ?
O2 H2 0.81(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 120.8(3) . . ?
O1 C1 C2 119.3(3) . . ?
O2 C1 C2 119.8(3) . . ?
C3 C2 C1 173.6(4) . . ?
C2 C3 C4 173.8(4) . . ?
C5 C4 C4 119.5(2) . 2_756 ?
C5 C4 C3 122.6(3) . . ?
C4 C4 C3 117.91(19) 2_756 . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C6 C6 C5 120.4(2) 2_756 . ?
C6 C6 H6 119.8 2_756 . ?
C5 C6 H6 119.8 . . ?
C1 O1 H1 109.5 . . ?
C1 O2 H2 124(6) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 164(4) . . . . ?
O2 C1 C2 C3 -15(4) . . . . ?
C1 C2 C3 C4 4(7) . . . . ?
C2 C3 C4 C5 -172(3) . . . . ?
C2 C3 C4 C4 7(4) . . . 2_756 ?
C4 C4 C5 C6 -0.6(6) 2_756 . . . ?
C3 C4 C5 C6 178.8(4) . . . . ?
C4 C5 C6 C6 0.3(7) . . . 2_756 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.82 1.86 2.677(5) 175.1 3_666
O2 H2 O2 0.80(8) 1.88(8) 2.623(6) 154(9) 2_756
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.055

# Attachment '12PPAdabco_new.cif'

#===========================================================================
data_ssr2
_database_code_depnum_ccdc_archive 'CCDC 656599'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O6'
_chemical_formula_weight         362.38

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   8.5222(4)
_cell_length_b                   9.1871(5)
_cell_length_c                   23.0730(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.067(2)
_cell_angle_gamma                90.00
_cell_volume                     1792.76(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6322
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      25.0

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9212
_exptl_absorpt_correction_T_max  0.9657
_exptl_absorpt_process_details   'SADABS(Buker, 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            30271
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         0.89
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3147
_reflns_number_gt                2408
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_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.
In DABCO, both nitrogens are protonated. The oxygens of one of the carboxylate
groups are disordered. The disordered oxygens pairs(O1, O1'; O2, O2')
are refined such that sum of their ocuppancies is constrained to 1.00(1).
All the hydrogens appeared in the difference Fourier map. However, the C-H
hydrogens were fixed at chemically meaningfull positions and riding model
refinement was performed ( C-H (aromatic) = 0.93Å;
C-H (secondary -CH2-) = 0.97Å; Uis0 = 1.2Ueq of the parent atom).
The N-H hydrogenS were isotropically refined. The N-H distance(0.95(1)Å)
was restrained to be in the vicinity of corresponding difference Fourier peak.
Similarly, the water hydrogens were restrained (O-H = 0.95(1)Å
and H...H 1.55(1)Å during refinement. All the donor-acceptor distances
are well with in the hydrogen bonding interaction range.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0597P)²+3.7519P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0016(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3147
_refine_ls_number_parameters     268
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.2269
_refine_ls_wR_factor_gt          0.2051
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3357(6) 0.9826(7) 0.1655(2) 0.0703(14) Uani 1 1 d . . .
C2 C 0.3120(5) 0.9731(5) 0.10189(18) 0.0535(11) Uani 1 1 d . A .
C3 C 0.2905(5) 0.9618(4) 0.05037(17) 0.0475(10) Uani 1 1 d . . .
C4 C 0.2645(5) 0.9465(4) -0.01196(16) 0.0438(9) Uani 1 1 d . A .
C5 C 0.1584(5) 1.0376(5) -0.04503(19) 0.0580(11) Uani 1 1 d . . .
H5 H 0.1031 1.1077 -0.0267 0.070 Uiso 1 1 calc R A .
C6 C 0.1346(6) 1.0242(6) -0.10523(19) 0.0632(12) Uani 1 1 d . A .
H6 H 0.0637 1.0857 -0.1272 0.076 Uiso 1 1 calc R . .
C7 C 0.2147(6) 0.9212(6) -0.13261(18) 0.0613(12) Uani 1 1 d . . .
H7 H 0.1987 0.9131 -0.1731 0.074 Uiso 1 1 calc R A .
C8 C 0.3182(5) 0.8300(5) -0.10061(17) 0.0555(11) Uani 1 1 d . A .
H8 H 0.3708 0.7593 -0.1197 0.067 Uiso 1 1 calc R . .
C9 C 0.3467(4) 0.8406(4) -0.04007(16) 0.0433(9) Uani 1 1 d . . .
C10 C 0.4622(5) 0.7504(5) -0.00770(16) 0.0478(10) Uani 1 1 d . A .
C11 C 0.5628(5) 0.6768(5) 0.01796(16) 0.0492(10) Uani 1 1 d . . .
C12 C 0.6965(5) 0.5958(5) 0.04821(16) 0.0483(10) Uani 1 1 d . A .
C13 C 0.6653(5) 0.5816(6) -0.13181(18) 0.0612(12) Uani 1 1 d . . .
H13A H 0.6389 0.6834 -0.1276 0.073 Uiso 1 1 calc R . .
H13B H 0.5777 0.5231 -0.1219 0.073 Uiso 1 1 calc R . .
C14 C 0.6951(5) 0.5506(7) -0.19391(19) 0.0691(14) Uani 1 1 d . . .
H14A H 0.6305 0.4692 -0.2094 0.083 Uiso 1 1 calc R . .
H14B H 0.6670 0.6349 -0.2183 0.083 Uiso 1 1 calc R . .
C15 C 0.9399(5) 0.6482(5) -0.10386(18) 0.0553(11) Uani 1 1 d . . .
H15A H 1.0371 0.6245 -0.0792 0.066 Uiso 1 1 calc R . .
H15B H 0.9100 0.7470 -0.0953 0.066 Uiso 1 1 calc R . .
C16 C 0.9637(6) 0.6350(7) -0.1674(2) 0.0754(16) Uani 1 1 d . . .
H16A H 0.9349 0.7257 -0.1875 0.091 Uiso 1 1 calc R . .
H16B H 1.0741 0.6153 -0.1707 0.091 Uiso 1 1 calc R . .
C17 C 0.8597(6) 0.3936(5) -0.10185(19) 0.0649(13) Uani 1 1 d . . .
H17A H 0.7725 0.3284 -0.0973 0.078 Uiso 1 1 calc R . .
H17B H 0.9481 0.3673 -0.0732 0.078 Uiso 1 1 calc R . .
C18 C 0.9065(7) 0.3793(7) -0.1626(2) 0.0835(17) Uani 1 1 d . . .
H18A H 1.0193 0.3619 -0.1606 0.100 Uiso 1 1 calc R . .
H18B H 0.8513 0.2981 -0.1827 0.100 Uiso 1 1 calc R . .
N1 N 0.8122(4) 0.5450(4) -0.09241(13) 0.0492(9) Uani 1 1 d D . .
N2 N 0.8646(5) 0.5157(5) -0.19431(15) 0.0674(12) Uani 1 1 d D . .
O1 O 0.3384(15) 1.0911(17) 0.1912(5) 0.095(3) Uani 0.601(11) 1 d P A 1
O2 O 0.3657(12) 0.8506(11) 0.1908(4) 0.075(2) Uani 0.601(11) 1 d P A 1
O1' O 0.249(2) 1.096(3) 0.1848(9) 0.095(3) Uani 0.399(11) 1 d P A 2
O2' O 0.417(2) 0.9187(17) 0.1959(6) 0.075(2) Uani 0.399(11) 1 d P A 2
O3 O 0.8024(3) 0.5570(4) 0.01825(12) 0.0648(9) Uani 1 1 d . . .
O4 O 0.6992(4) 0.5706(4) 0.10084(12) 0.0744(11) Uani 1 1 d . . .
O5 O 0.8683(9) 0.8463(10) 0.2678(3) 0.173(3) Uani 1 1 d D . .
O6 O 0.8685(6) 0.1860(6) 0.29715(17) 0.1008(14) Uani 1 1 d D . .
H1 H 0.798(6) 0.555(5) -0.0524(7) 0.074(14) Uiso 1 1 d D . .
H2 H 0.875(7) 0.487(6) -0.2333(10) 0.11(2) Uiso 1 1 d D . .
H5A H 0.84(2) 0.763(11) 0.244(7) 0.41(7) Uiso 1 1 d D . .
H5B H 0.797(19) 0.924(13) 0.256(8) 0.41(7) Uiso 1 1 d D . .
H6A H 0.969(5) 0.232(8) 0.302(2) 0.15(3) Uiso 1 1 d D . .
H6B H 0.836(6) 0.169(7) 0.3343(11) 0.11(2) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.078(3) 0.098(4) 0.037(2) -0.005(3) 0.016(2) -0.013(3)
C2 0.064(3) 0.055(3) 0.043(2) 0.0017(19) 0.0118(19) 0.001(2)
C3 0.057(2) 0.043(2) 0.043(2) 0.0041(17) 0.0089(17) 0.0010(19)
C4 0.048(2) 0.044(2) 0.0394(19) 0.0053(17) 0.0070(16) -0.0048(18)
C5 0.065(3) 0.051(3) 0.058(3) 0.005(2) 0.006(2) 0.011(2)
C6 0.068(3) 0.065(3) 0.053(3) 0.015(2) -0.006(2) 0.008(2)
C7 0.067(3) 0.076(3) 0.040(2) 0.006(2) 0.0020(19) -0.003(3)
C8 0.055(2) 0.070(3) 0.041(2) -0.006(2) 0.0043(18) 0.007(2)
C9 0.041(2) 0.049(2) 0.0397(19) 0.0016(17) 0.0037(15) -0.0007(18)
C10 0.046(2) 0.058(3) 0.039(2) -0.0018(19) 0.0047(17) 0.000(2)
C11 0.048(2) 0.061(3) 0.038(2) -0.0010(19) 0.0067(17) 0.002(2)
C12 0.050(2) 0.058(3) 0.036(2) 0.0032(18) 0.0026(17) 0.006(2)
C13 0.047(2) 0.090(4) 0.047(2) 0.006(2) 0.0088(18) 0.007(2)
C14 0.052(3) 0.109(4) 0.045(2) 0.003(3) -0.0008(19) 0.009(3)
C15 0.058(3) 0.056(3) 0.051(2) 0.007(2) 0.0040(19) -0.005(2)
C16 0.061(3) 0.113(5) 0.054(3) 0.021(3) 0.010(2) -0.010(3)
C17 0.081(3) 0.056(3) 0.054(3) 0.004(2) -0.003(2) 0.000(2)
C18 0.101(4) 0.085(4) 0.062(3) -0.012(3) 0.000(3) 0.031(3)
N1 0.055(2) 0.060(2) 0.0336(16) 0.0041(16) 0.0077(14) 0.0000(17)
N2 0.061(2) 0.107(3) 0.0349(18) 0.001(2) 0.0082(16) 0.019(2)
O1 0.149(11) 0.091(3) 0.049(3) -0.017(3) 0.026(7) -0.018(10)
O2 0.094(6) 0.086(7) 0.046(2) 0.015(4) 0.017(3) 0.011(4)
O1' 0.149(11) 0.091(3) 0.049(3) -0.017(3) 0.026(7) -0.018(10)
O2' 0.094(6) 0.086(7) 0.046(2) 0.015(4) 0.017(3) 0.011(4)
O3 0.0522(17) 0.103(3) 0.0396(15) 0.0069(16) 0.0080(13) 0.0196(17)
O4 0.085(2) 0.104(3) 0.0359(15) 0.0148(17) 0.0125(14) 0.029(2)
O5 0.143(5) 0.211(7) 0.151(5) 0.044(5) -0.043(4) -0.054(5)
O6 0.105(3) 0.127(4) 0.073(3) 0.030(3) 0.021(2) 0.005(3)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2' 1.092(16) . ?
C1 O1 1.157(15) . ?
C1 O2 1.357(12) . ?
C1 O1' 1.38(3) . ?
C1 C2 1.460(6) . ?
C2 C3 1.185(5) . ?
C3 C4 1.435(5) . ?
C4 C5 1.390(6) . ?
C4 C9 1.404(5) . ?
C5 C6 1.384(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.367(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.365(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.391(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.426(6) . ?
C10 C11 1.190(6) . ?
C11 C12 1.464(6) . ?
C12 O4 1.234(4) . ?
C12 O3 1.254(5) . ?
C13 N1 1.492(5) . ?
C13 C14 1.512(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.481(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N1 1.490(5) . ?
C15 C16 1.510(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.474(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N1 1.472(6) . ?
C17 C18 1.510(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N2 1.473(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N1 H1 0.949(10) . ?
N2 H2 0.952(10) . ?
O5 H5A 0.96(11) . ?
O5 H5B 0.96(13) . ?
O6 H6A 0.950(10) . ?
O6 H6B 0.946(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2' C1 O1 99.4(10) . . ?
O2' C1 O2 34.1(8) . . ?
O1 C1 O2 123.9(9) . . ?
O2' C1 O1' 121.2(12) . . ?
O1 C1 O1' 33.2(9) . . ?
O2 C1 O1' 128.1(11) . . ?
O2' C1 C2 127.7(10) . . ?
O1 C1 C2 123.9(9) . . ?
O2 C1 C2 112.0(6) . . ?
O1' C1 C2 110.8(10) . . ?
C3 C2 C1 178.1(5) . . ?
C2 C3 C4 179.4(5) . . ?
C5 C4 C9 119.5(4) . . ?
C5 C4 C3 120.1(4) . . ?
C9 C4 C3 120.5(4) . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 120.1(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 121.4(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C4 118.5(4) . . ?
C8 C9 C10 120.6(4) . . ?
C4 C9 C10 120.8(3) . . ?
C11 C10 C9 177.5(4) . . ?
C10 C11 C12 175.0(5) . . ?
O4 C12 O3 124.2(4) . . ?
O4 C12 C11 118.9(4) . . ?
O3 C12 C11 116.9(3) . . ?
N1 C13 C14 108.0(3) . . ?
N1 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
N1 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
N2 C14 C13 108.9(3) . . ?
N2 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
N2 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
N1 C15 C16 108.1(4) . . ?
N1 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
N1 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
N2 C16 C15 109.2(4) . . ?
N2 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
N2 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
N1 C17 C18 109.2(4) . . ?
N1 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 . . ?
N1 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
N2 C18 C17 108.1(4) . . ?
N2 C18 H18A 110.1 . . ?
C17 C18 H18A 110.1 . . ?
N2 C18 H18B 110.1 . . ?
C17 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
C17 N1 C15 110.8(4) . . ?
C17 N1 C13 110.3(4) . . ?
C15 N1 C13 109.0(3) . . ?
C17 N1 H1 108(3) . . ?
C15 N1 H1 107(3) . . ?
C13 N1 H1 112(3) . . ?
C18 N2 C16 109.4(4) . . ?
C18 N2 C14 111.0(4) . . ?
C16 N2 C14 110.2(4) . . ?
C18 N2 H2 101(4) . . ?
C16 N2 H2 119(4) . . ?
C14 N2 H2 106(4) . . ?
H5A O5 H5B 109(12) . . ?
H6A O6 H6B 109.6(16) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2' C1 C2 C3 75(16) . . . . ?
O1 C1 C2 C3 -144(16) . . . . ?
O2 C1 C2 C3 40(16) . . . . ?
O1' C1 C2 C3 -110(16) . . . . ?
C1 C2 C3 C4 -37(54) . . . . ?
C2 C3 C4 C5 144(43) . . . . ?
C2 C3 C4 C9 -37(44) . . . . ?
C9 C4 C5 C6 -0.3(7) . . . . ?
C3 C4 C5 C6 179.2(4) . . . . ?
C4 C5 C6 C7 0.2(7) . . . . ?
C5 C6 C7 C8 0.4(8) . . . . ?
C6 C7 C8 C9 -1.0(7) . . . . ?
C7 C8 C9 C4 1.0(7) . . . . ?
C7 C8 C9 C10 -176.2(4) . . . . ?
C5 C4 C9 C8 -0.3(6) . . . . ?
C3 C4 C9 C8 -179.8(4) . . . . ?
C5 C4 C9 C10 176.8(4) . . . . ?
C3 C4 C9 C10 -2.6(6) . . . . ?
C8 C9 C10 C11 53(11) . . . . ?
C4 C9 C10 C11 -124(10) . . . . ?
C9 C10 C11 C12 29(14) . . . . ?
C10 C11 C12 O4 121(5) . . . . ?
C10 C11 C12 O3 -59(5) . . . . ?
N1 C13 C14 N2 -8.0(6) . . . . ?
N1 C15 C16 N2 -5.5(5) . . . . ?
N1 C17 C18 N2 -8.8(6) . . . . ?
C18 C17 N1 C15 -54.9(5) . . . . ?
C18 C17 N1 C13 65.8(5) . . . . ?
C16 C15 N1 C17 63.2(5) . . . . ?
C16 C15 N1 C13 -58.4(5) . . . . ?
C14 C13 N1 C17 -55.4(5) . . . . ?
C14 C13 N1 C15 66.4(5) . . . . ?
C17 C18 N2 C16 66.6(5) . . . . ?
C17 C18 N2 C14 -55.2(6) . . . . ?
C15 C16 N2 C18 -58.1(5) . . . . ?
C15 C16 N2 C14 64.2(5) . . . . ?
C13 C14 N2 C18 65.4(6) . . . . ?
C13 C14 N2 C16 -56.0(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.952(10) 1.88(2) 2.802(14) 163(6) 4_675
N1 H1 O3 0.949(10) 1.626(14) 2.567(4) 170(5) .
O5 H5A O6 0.96(11) 2.03(14) 2.783(8) 135(15) 2_655
O6 H6A O2 0.950(10) 1.77(2) 2.709(11) 169(8) 2_645
O5 H5B O6 0.96(13) 2.64(16) 3.193(11) 118(13) 1_565
O6 H6B O4 0.946(10) 1.81(3) 2.707(5) 158(6) 2_645

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.071

# Attachment '13PPA.cif'

data_13pp
_database_code_depnum_ccdc_archive 'CCDC 656600'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 O12'
_chemical_formula_sum            'C24 H20 O12'
_chemical_formula_weight         500.40

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-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                   56.173(5)
_cell_length_b                   3.777(5)
_cell_length_c                   11.660(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 96.062(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2460(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3180
_cell_measurement_theta_min      5.832
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9122
_exptl_absorpt_correction_T_max  0.9512
_exptl_absorpt_process_details   'Bruker(SADABS, 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11518
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_min       -65
_diffrn_reflns_limit_h_max       66
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2167
_reflns_number_gt                1752
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.
All the hydrogens could be located in difference Fourier map. However,
the C-H and carboxylic hydrogens were fixed (C-H= 0.93Å, U=1.2UisoC
and O-H=0.820Å, U=1.5UisoO) chemically meaningful positions and were
given riding model refinement. Water hydrogens were refined with restraints
(O-H= 0.920(1)Å, H...H=1.48Å,).Thermal parameters of water hydrogens
were refined isotropically. The restraints were applied to keep the
hydrogens in the vicinity of the Fourier peak position after refinement.
All the donor-acceptor distances are with in the hydrogen bonding
interaction range.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1117P)²+0.3936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0016(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2167
_refine_ls_number_parameters     180
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1783
_refine_ls_wR_factor_gt          0.1659
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.95303(4) -0.7835(7) 0.1188(2) 0.0605(6) Uani 1 1 d . . .
C2 C 0.93230(4) -0.6397(7) 0.0493(2) 0.0597(6) Uani 1 1 d . . .
C3 C 0.91507(3) -0.5243(6) -0.00628(18) 0.0521(6) Uani 1 1 d . . .
C4 C 0.89349(3) -0.3884(5) -0.06766(16) 0.0424(5) Uani 1 1 d . . .
C5 C 0.87265(3) -0.3943(5) -0.01459(15) 0.0397(5) Uani 1 1 d . . .
H5 H 0.8728 -0.4865 0.0595 0.048 Uiso 1 1 calc R . .
C6 C 0.85141(3) -0.2641(5) -0.07060(16) 0.0398(5) Uani 1 1 d . . .
C7 C 0.85108(4) -0.1282(5) -0.18193(16) 0.0459(5) Uani 1 1 d . . .
H7 H 0.8369 -0.0425 -0.2207 0.055 Uiso 1 1 calc R . .
C8 C 0.87194(4) -0.1228(6) -0.23363(17) 0.0507(5) Uani 1 1 d . . .
H8 H 0.8718 -0.0300 -0.3076 0.061 Uiso 1 1 calc R . .
C9 C 0.89302(4) -0.2508(6) -0.17883(18) 0.0495(5) Uani 1 1 d . . .
H9 H 0.9069 -0.2458 -0.2157 0.059 Uiso 1 1 calc R . .
C10 C 0.83032(4) -0.2602(5) -0.01139(17) 0.0473(5) Uani 1 1 d . . .
C11 C 0.81343(4) -0.2524(6) 0.04298(19) 0.0524(6) Uani 1 1 d . . .
C12 C 0.79338(4) -0.2129(6) 0.10980(18) 0.0479(5) Uani 1 1 d . . .
O1 O 0.94859(3) -0.8663(7) 0.22133(17) 0.0950(8) Uani 1 1 d . . .
H1 H 0.9607 -0.9476 0.2572 0.142 Uiso 1 1 calc R . .
O2 O 0.97194(3) -0.8237(7) 0.08257(16) 0.0871(7) Uani 1 1 d . . .
O3 O 0.79762(3) -0.3400(5) 0.21371(13) 0.0636(5) Uani 1 1 d . . .
H3 H 0.7858 -0.3123 0.2483 0.095 Uiso 1 1 calc R . .
O4 O 0.77504(3) -0.0701(5) 0.07135(13) 0.0636(5) Uani 1 1 d . . .
O5 O 0.73513(3) 0.2923(6) 0.15677(15) 0.0737(6) Uani 1 1 d D . .
O6 O 0.98249(4) -1.1529(8) 0.35093(18) 0.1027(9) Uani 1 1 d D . .
H5A H 0.7487(4) 0.164(8) 0.147(2) 0.126(14) Uiso 1 1 d D . .
H5B H 0.7297(5) 0.391(8) 0.0868(13) 0.100(10) Uiso 1 1 d D . .
H6A H 0.9789(5) -1.187(11) 0.4253(10) 0.117(13) Uiso 1 1 d D . .
H6B H 0.99883(13) -1.130(19) 0.353(3) 0.22(3) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0372(12) 0.0821(17) 0.0606(14) -0.0113(11) -0.0013(9) 0.0064(10)
C2 0.0387(12) 0.0722(16) 0.0668(14) -0.0101(11) -0.0016(10) 0.0057(10)
C3 0.0387(11) 0.0563(13) 0.0603(12) -0.0097(10) 0.0013(9) 0.0017(9)
C4 0.0378(10) 0.0426(11) 0.0460(10) -0.0083(8) 0.0003(8) 0.0006(7)
C5 0.0436(10) 0.0403(10) 0.0350(9) -0.0027(7) 0.0036(7) 0.0039(7)
C6 0.0393(10) 0.0372(10) 0.0427(10) -0.0057(7) 0.0034(7) 0.0007(7)
C7 0.0504(11) 0.0427(11) 0.0428(10) -0.0012(8) -0.0038(8) 0.0062(8)
C8 0.0680(14) 0.0476(12) 0.0366(10) 0.0028(8) 0.0064(9) -0.0004(9)
C9 0.0501(12) 0.0492(12) 0.0516(12) -0.0057(9) 0.0162(9) -0.0041(8)
C10 0.0406(11) 0.0484(12) 0.0531(11) -0.0035(9) 0.0059(9) 0.0033(8)
C11 0.0416(11) 0.0609(14) 0.0546(12) -0.0019(10) 0.0049(9) 0.0041(9)
C12 0.0373(10) 0.0590(13) 0.0471(11) -0.0047(9) 0.0036(8) -0.0014(8)
O1 0.0481(10) 0.172(2) 0.0647(12) 0.0116(12) 0.0039(8) 0.0200(11)
O2 0.0413(10) 0.150(2) 0.0690(11) 0.0004(11) 0.0040(8) 0.0246(10)
O3 0.0451(9) 0.0938(13) 0.0519(9) 0.0084(8) 0.0060(7) 0.0073(7)
O4 0.0417(9) 0.0981(13) 0.0519(9) 0.0058(8) 0.0089(6) 0.0156(8)
O5 0.0594(11) 0.1089(15) 0.0557(10) 0.0117(9) 0.0192(8) 0.0230(9)
O6 0.0563(12) 0.181(3) 0.0687(13) 0.0164(14) -0.0047(9) -0.0034(13)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.193(3) . ?
C1 O1 1.286(3) . ?
C1 C2 1.452(3) . ?
C2 C3 1.189(3) . ?
C3 C4 1.436(3) . ?
C4 C5 1.381(3) . ?
C4 C9 1.394(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(3) . ?
C6 C10 1.433(3) . ?
C7 C8 1.374(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.196(3) . ?
C11 C12 1.443(3) . ?
C12 O4 1.207(3) . ?
C12 O3 1.301(3) . ?
O1 H1 0.8200 . ?
O3 H3 0.8200 . ?
O5 H5A 0.92(2) . ?
O5 H5B 0.92(2) . ?
O6 H6A 0.920(15) . ?
O6 H6B 0.920(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 124.4(2) . . ?
O2 C1 C2 122.8(2) . . ?
O1 C1 C2 112.7(2) . . ?
C3 C2 C1 178.9(3) . . ?
C2 C3 C4 176.6(2) . . ?
C5 C4 C9 119.25(17) . . ?
C5 C4 C3 118.82(18) . . ?
C9 C4 C3 121.94(18) . . ?
C4 C5 C6 120.71(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.64(18) . . ?
C5 C6 C10 119.36(17) . . ?
C7 C6 C10 120.96(17) . . ?
C8 C7 C6 119.09(18) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 121.63(18) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C4 119.68(19) . . ?
C8 C9 H9 120.2 . . ?
C4 C9 H9 120.2 . . ?
C11 C10 C6 176.7(2) . . ?
C10 C11 C12 175.4(2) . . ?
O4 C12 O3 125.15(19) . . ?
O4 C12 C11 121.99(19) . . ?
O3 C12 C11 112.85(18) . . ?
C1 O1 H1 109.5 . . ?
C12 O3 H3 109.5 . . ?
H5A O5 H5B 108(2) . . ?
H6A O6 H6B 108(3) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 160(14) . . . . ?
O1 C1 C2 C3 -19(14) . . . . ?
C1 C2 C3 C4 18(17) . . . . ?
C2 C3 C4 C5 -4(4) . . . . ?
C2 C3 C4 C9 176(4) . . . . ?
C9 C4 C5 C6 -0.2(3) . . . . ?
C3 C4 C5 C6 179.72(18) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C4 C5 C6 C10 -177.36(17) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C10 C6 C7 C8 177.12(18) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C4 -0.4(3) . . . . ?
C5 C4 C9 C8 0.2(3) . . . . ?
C3 C4 C9 C8 -179.7(2) . . . . ?
C5 C6 C10 C11 38(4) . . . . ?
C7 C6 C10 C11 -140(4) . . . . ?
C6 C10 C11 C12 65(5) . . . . ?
C10 C11 C12 O4 73(3) . . . . ?
C10 C11 C12 O3 -106(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O6 0.82 1.74 2.545(3) 168.8 .
O3 H3 O5 0.82 1.74 2.550(2) 167.8 4_645
O5 H5A O4 0.92(2) 2.009(10) 2.892(2) 161(3) .
O5 H5B O4 0.92(2) 1.955(7) 2.860(3) 167(3) 7_655
O6 H6A O2 0.920(15) 1.915(7) 2.827(3) 171(4) 6_536
O6 H6B O2 0.920(13) 2.08(4) 2.878(3) 144(6) 2_755

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.040
# end Validation Reply Form

# Attachment '14PPA.cif'

data_saran1
_database_code_depnum_ccdc_archive 'CCDC 656601'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 O6'
_chemical_formula_sum            'C12 H10 O6'
_chemical_formula_weight         250.20

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.7812(3)
_cell_length_b                   6.1345(5)
_cell_length_c                   13.3677(11)
_cell_angle_alpha                101.929(5)
_cell_angle_beta                 93.522(5)
_cell_angle_gamma                93.507(5)
_cell_volume                     301.94(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1570
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      28.1

_exptl_crystal_description       prisamatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             130
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8811
_exptl_absorpt_correction_T_max  0.9627
_exptl_absorpt_process_details   'Bruker(SADABS, 1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD diffractometer'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3209
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1051
_reflns_number_gt                884
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.
All the hydrogens could be located in difference Fourier map. However,
the C-H and carboxylic hydrogens were fixed (C-H= 0.93Å, U=1.2UisoC
and O-H=0.820Å) chemically meaningful positions and were given riding
model refinement. Water hydrogens were refined with restraints
(O-H= 0.930(1)Å, H...H=1.50Å). Thermal parameters of water and O-H
hydrogens were refined isotropically. The restraints were applied
The restraints were applied to keep the hydrogens in the vicinity of the
Fourier peak position after refinement. All the donor-acceptor distances
are well with in the hydrogen bonding interaction range.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0666P)²+0.0799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1051
_refine_ls_number_parameters     91
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1298
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5992(5) 0.6609(3) 0.31298(13) 0.0470(5) Uani 1 1 d . . .
C2 C 0.4417(5) 0.4889(3) 0.22885(14) 0.0506(5) Uani 1 1 d . . .
C3 C 0.3139(4) 0.3445(3) 0.16003(13) 0.0471(5) Uani 1 1 d . . .
C4 C 0.1562(4) 0.1696(3) 0.07825(12) 0.0416(4) Uani 1 1 d . . .
C5 C 0.1247(5) 0.2003(3) -0.02198(13) 0.0482(5) Uani 1 1 d . . .
H5 H 0.2095 0.3349 -0.0366 0.058 Uiso 1 1 calc R . .
C6 C 0.0310(5) -0.0328(3) 0.09952(13) 0.0488(5) Uani 1 1 d . . .
H6 H 0.0529 -0.0546 0.1664 0.059 Uiso 1 1 calc R . .
O1 O 0.7510(5) 0.6188(2) 0.38734(11) 0.0768(6) Uani 1 1 d . . .
O2 O 0.5609(5) 0.8593(2) 0.29870(11) 0.0713(5) Uani 1 1 d . . .
H2 H 0.6681 0.9507 0.3460 0.108(10) Uiso 1 1 calc R . .
O3 O 0.8554(7) 1.1901(3) 0.42513(16) 0.1173(9) Uani 1 1 d D . .
H3A H 0.965(11) 1.208(5) 0.4909(13) 0.193(18) Uiso 1 1 d D . .
H3B H 0.794(10) 1.330(2) 0.416(2) 0.153(14) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0523(10) 0.0428(10) 0.0395(9) -0.0012(7) -0.0085(8) 0.0000(8)
C2 0.0507(11) 0.0489(11) 0.0459(10) -0.0005(8) -0.0077(8) 0.0011(8)
C3 0.0434(10) 0.0470(11) 0.0440(10) -0.0033(8) -0.0063(8) 0.0020(8)
C4 0.0354(8) 0.0408(9) 0.0415(9) -0.0047(7) -0.0062(7) 0.0032(7)
C5 0.0509(10) 0.0414(10) 0.0480(10) 0.0044(7) -0.0056(8) -0.0033(7)
C6 0.0537(11) 0.0507(11) 0.0374(9) 0.0031(7) -0.0071(8) -0.0004(8)
O1 0.1163(14) 0.0462(9) 0.0566(9) -0.0001(6) -0.0413(9) 0.0029(8)
O2 0.1057(13) 0.0436(8) 0.0557(9) 0.0041(6) -0.0325(8) -0.0051(7)
O3 0.185(2) 0.0488(11) 0.0983(14) -0.0002(9) -0.0785(15) -0.0014(12)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.199(2) . ?
C1 O2 1.286(2) . ?
C1 C2 1.443(2) . ?
C2 C3 1.192(2) . ?
C3 C4 1.435(2) . ?
C4 C5 1.390(2) . ?
C4 C6 1.391(3) . ?
C5 C6 1.374(2) 2 ?
C5 H5 0.9300 . ?
C6 C5 1.374(2) 2 ?
C6 H6 0.9300 . ?
O2 H2 0.8200 . ?
O3 H3A 0.93(2) . ?
O3 H3B 0.933(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 124.67(17) . . ?
O1 C1 C2 122.35(17) . . ?
O2 C1 C2 112.97(15) . . ?
C3 C2 C1 179.0(2) . . ?
C2 C3 C4 179.08(19) . . ?
C5 C4 C6 119.55(15) . . ?
C5 C4 C3 120.78(16) . . ?
C6 C4 C3 119.66(15) . . ?
C6 C5 C4 120.32(17) 2 . ?
C6 C5 H5 119.8 2 . ?
C4 C5 H5 119.8 . . ?
C5 C6 C4 120.13(16) 2 . ?
C5 C6 H6 119.9 2 . ?
C4 C6 H6 119.9 . . ?
C1 O2 H2 109.5 . . ?
H3A O3 H3B 108(3) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -8(12) . . . . ?
O2 C1 C2 C3 172(100) . . . . ?
C1 C2 C3 C4 72(19) . . . . ?
C2 C3 C4 C5 145(13) . . . . ?
C2 C3 C4 C6 -35(13) . . . . ?
C6 C4 C5 C6 0.5(3) . . . 2 ?
C3 C4 C5 C6 -179.14(15) . . . 2 ?
C5 C4 C6 C5 -0.4(3) . . . 2 ?
C3 C4 C6 C5 179.15(15) . . . 2 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.82 1.71 2.508(2) 164.6 .
O3 H3A O1 0.93(2) 1.965(16) 2.826(2) 153(3) 2_776
O3 H3B O1 0.933(17) 1.906(8) 2.825(2) 169(4) 1_565

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.036


# Attachment '14PPAdabco.cif'

data_saro
_database_code_depnum_ccdc_archive 'CCDC 656602'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N2 O4'
_chemical_formula_sum            'C18 H18 N2 O4'
_chemical_formula_weight         326.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   9.5230(18)
_cell_length_b                   17.603(5)
_cell_length_c                   9.8656(17)
_cell_angle_alpha                90.000(18)
_cell_angle_beta                 103.425(13)
_cell_angle_gamma                90.000(19)
_cell_volume                     1608.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      15
_cell_measurement_theta_max      20

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_factor_muR        0.000
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was 4
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_absorpt_correction_T_min  0.9412
_exptl_absorpt_correction_T_max  0.9992

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'cad4 diffractometer'
_diffrn_measurement_method       'omega twotheta'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  '1 hour'
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3111
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.77
_diffrn_reflns_theta_max         67.92
_reflns_number_total             2928
_reflns_number_gt                1921
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'cad4 system software'
_computing_cell_refinement       'cad4 system software'
_computing_data_reduction        'xcad4(Harms et al., 1995)'
_computing_structure_solution    'sir92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3(Farrugia et al., 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.
Hydrogens of DABCO nitrogens were located in difference Fourier map and
refined isotropically. All other hydrogens were fixed at chemically
meaningful positions and were given riding model refinement.
All the donor-acceptor distances are well with in the hydrogen bonding
interaction range.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1344P)²+1.7104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2928
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.2783
_refine_ls_wR_factor_gt          0.2672
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2809(4) 0.6400(2) 0.3003(3) 0.0486(9) Uani 1 1 d . . .
C2 C 0.1957(4) 0.6318(2) 0.1565(4) 0.0489(9) Uani 1 1 d . . .
C3 C 0.1316(4) 0.6283(2) 0.0376(3) 0.0498(10) Uani 1 1 d . . .
C4 C 0.0582(4) 0.6246(2) -0.1075(3) 0.0476(9) Uani 1 1 d . . .
C5 C 0.0274(4) 0.5554(2) -0.1744(3) 0.0458(9) Uani 1 1 d . . .
H5 H 0.0526 0.5105 -0.1250 0.055 Uiso 1 1 calc R . .
C6 C -0.0405(4) 0.5526(2) -0.3142(3) 0.0483(9) Uani 1 1 d . . .
H6 H -0.0604 0.5060 -0.3589 0.058 Uiso 1 1 calc R . .
C7 C -0.0792(3) 0.6198(2) -0.3880(3) 0.0434(9) Uani 1 1 d . . .
C8 C -0.0493(4) 0.6890(2) -0.3213(3) 0.0516(10) Uani 1 1 d . . .
H8 H -0.0753 0.7338 -0.3706 0.062 Uiso 1 1 calc R . .
C9 C 0.0192(4) 0.6919(2) -0.1815(3) 0.0489(9) Uani 1 1 d . . .
H9 H 0.0391 0.7385 -0.1369 0.059 Uiso 1 1 calc R . .
C10 C -0.1526(4) 0.6167(2) -0.5342(3) 0.0478(9) Uani 1 1 d . . .
C11 C -0.2145(4) 0.6142(2) -0.6532(3) 0.0489(9) Uani 1 1 d . . .
C12 C -0.2907(4) 0.6085(2) -0.8010(3) 0.0462(9) Uani 1 1 d . . .
C13 C 0.4610(4) 0.4459(2) 0.3347(4) 0.0556(10) Uani 1 1 d . . .
H13A H 0.5165 0.4926 0.3442 0.067 Uiso 1 1 calc R . .
H13B H 0.3949 0.4488 0.3960 0.067 Uiso 1 1 calc R . .
C14 C 0.3768(4) 0.4364(2) 0.1850(4) 0.0535(10) Uani 1 1 d . . .
H14A H 0.2743 0.4333 0.1815 0.064 Uiso 1 1 calc R . .
H14B H 0.3932 0.4797 0.1299 0.064 Uiso 1 1 calc R . .
C15 C 0.5817(4) 0.3710(2) 0.1333(4) 0.0458(9) Uani 1 1 d . . .
H15A H 0.6004 0.4152 0.0815 0.055 Uiso 1 1 calc R . .
H15B H 0.6133 0.3262 0.0914 0.055 Uiso 1 1 calc R . .
C16 C 0.6640(4) 0.3776(2) 0.2846(4) 0.0519(10) Uani 1 1 d . . .
H16A H 0.7277 0.3343 0.3098 0.062 Uiso 1 1 calc R . .
H16B H 0.7223 0.4234 0.2975 0.062 Uiso 1 1 calc R . .
C17 C 0.3961(4) 0.2984(2) 0.2097(3) 0.0543(10) Uani 1 1 d . . .
H17A H 0.4287 0.2523 0.1728 0.065 Uiso 1 1 calc R . .
H17B H 0.2931 0.2940 0.2029 0.065 Uiso 1 1 calc R . .
C18 C 0.4752(5) 0.3089(2) 0.3609(4) 0.0592(11) Uani 1 1 d . . .
H18A H 0.4064 0.3111 0.4195 0.071 Uiso 1 1 calc R . .
H18B H 0.5394 0.2662 0.3909 0.071 Uiso 1 1 calc R . .
N1 N 0.4260(3) 0.36550(16) 0.1279(3) 0.0408(7) Uani 1 1 d . . .
N2 N 0.5592(3) 0.38024(17) 0.3740(3) 0.0467(8) Uani 1 1 d . . .
O1 O 0.3363(7) 0.6993(3) 0.3329(4) 0.177(3) Uani 1 1 d . . .
O2 O 0.2865(5) 0.5877(2) 0.3786(3) 0.1027(15) Uani 1 1 d . . .
O3 O -0.2853(3) 0.66476(16) -0.8755(2) 0.0613(9) Uani 1 1 d . . .
O4 O -0.3524(4) 0.54906(18) -0.8408(3) 0.0936(14) Uani 1 1 d . . .
H1 H 0.375(4) 0.361(2) 0.033(4) 0.054(11) Uiso 1 1 d . . .
H2 H 0.616(5) 0.384(2) 0.466(5) 0.077(14) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.057(2) 0.051(2) 0.0274(17) 0.0009(15) -0.0116(15) -0.0092(17)
C2 0.051(2) 0.059(2) 0.0287(18) 0.0050(15) -0.0075(15) 0.0002(17)
C3 0.045(2) 0.072(3) 0.0258(18) -0.0005(15) -0.0050(14) 0.0010(17)
C4 0.0355(18) 0.076(3) 0.0248(16) 0.0011(16) -0.0053(13) 0.0022(16)
C5 0.0408(18) 0.064(2) 0.0278(16) 0.0113(15) -0.0029(14) 0.0039(16)
C6 0.0415(19) 0.066(2) 0.0308(17) -0.0006(16) -0.0056(14) 0.0015(16)
C7 0.0350(17) 0.069(2) 0.0212(15) 0.0019(14) -0.0035(12) 0.0060(16)
C8 0.051(2) 0.065(2) 0.0315(17) 0.0038(16) -0.0053(15) 0.0148(18)
C9 0.046(2) 0.064(2) 0.0301(17) -0.0005(15) -0.0050(14) 0.0032(17)
C10 0.0453(19) 0.069(2) 0.0221(17) 0.0023(15) -0.0056(14) 0.0055(17)
C11 0.052(2) 0.059(2) 0.0281(18) 0.0033(15) -0.0062(15) 0.0031(17)
C12 0.050(2) 0.049(2) 0.0308(18) 0.0019(15) -0.0093(14) -0.0001(16)
C13 0.062(2) 0.066(3) 0.0356(19) -0.0094(17) 0.0057(17) -0.0021(19)
C14 0.056(2) 0.059(2) 0.0395(19) -0.0021(16) -0.0008(16) 0.0169(18)
C15 0.0453(19) 0.056(2) 0.0359(18) -0.0034(15) 0.0090(14) -0.0018(16)
C16 0.0385(19) 0.069(3) 0.042(2) 0.0014(17) -0.0031(15) -0.0042(17)
C17 0.064(2) 0.059(2) 0.0321(18) 0.0007(16) -0.0036(16) -0.0208(19)
C18 0.075(3) 0.063(2) 0.0328(18) 0.0072(17) -0.0014(17) -0.019(2)
N1 0.0428(16) 0.0548(17) 0.0192(13) 0.0004(11) -0.0042(11) -0.0010(13)
N2 0.0509(18) 0.0598(19) 0.0203(14) 0.0034(12) -0.0102(12) -0.0089(14)
O1 0.269(6) 0.112(3) 0.086(3) 0.030(3) -0.090(4) -0.104(4)
O2 0.151(3) 0.087(2) 0.0398(16) 0.0140(17) -0.0390(19) -0.044(2)
O3 0.083(2) 0.0590(17) 0.0273(12) 0.0058(11) -0.0159(12) -0.0149(14)
O4 0.144(3) 0.067(2) 0.0444(17) 0.0092(14) -0.0281(18) -0.038(2)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.179(5) . ?
C1 O2 1.195(5) . ?
C1 C2 1.469(4) . ?
C2 C3 1.191(5) . ?
C3 C4 1.441(4) . ?
C4 C5 1.385(5) . ?
C4 C9 1.395(5) . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(5) . ?
C7 C10 1.450(4) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.186(5) . ?
C11 C12 1.474(4) . ?
C12 O4 1.219(4) . ?
C12 O3 1.242(4) . ?
C13 N2 1.481(5) . ?
C13 C14 1.517(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.489(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N1 1.475(4) . ?
C15 C16 1.521(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.478(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N1 1.495(4) . ?
C17 C18 1.518(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N2 1.479(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N1 H1 0.96(4) . ?
N2 H2 0.94(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 123.7(4) . . ?
O1 C1 C2 117.5(4) . . ?
O2 C1 C2 118.7(3) . . ?
C3 C2 C1 176.2(4) . . ?
C2 C3 C4 178.2(4) . . ?
C5 C4 C9 119.7(3) . . ?
C5 C4 C3 120.9(3) . . ?
C9 C4 C3 119.4(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 C10 120.4(3) . . ?
C6 C7 C10 119.7(3) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 119.9(4) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?
C11 C10 C7 179.0(4) . . ?
C10 C11 C12 178.2(4) . . ?
O4 C12 O3 125.2(3) . . ?
O4 C12 C11 117.8(3) . . ?
O3 C12 C11 116.9(3) . . ?
N2 C13 C14 109.1(3) . . ?
N2 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
N2 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
N1 C14 C13 108.6(3) . . ?
N1 C14 H14A 110.0 . . ?
C13 C14 H14A 110.0 . . ?
N1 C14 H14B 110.0 . . ?
C13 C14 H14B 110.0 . . ?
H14A C14 H14B 108.3 . . ?
N1 C15 C16 109.0(3) . . ?
N1 C15 H15A 109.9 . . ?
C16 C15 H15A 109.9 . . ?
N1 C15 H15B 109.9 . . ?
C16 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
N2 C16 C15 108.8(3) . . ?
N2 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
N2 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
N1 C17 C18 108.7(3) . . ?
N1 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
N1 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
N2 C18 C17 108.9(3) . . ?
N2 C18 H18A 109.9 . . ?
C17 C18 H18A 109.9 . . ?
N2 C18 H18B 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C15 N1 C14 109.4(3) . . ?
C15 N1 C17 110.4(3) . . ?
C14 N1 C17 110.0(3) . . ?
C15 N1 H1 109(2) . . ?
C14 N1 H1 108(2) . . ?
C17 N1 H1 110(2) . . ?
C16 N2 C18 110.3(3) . . ?
C16 N2 C13 110.0(3) . . ?
C18 N2 C13 110.1(3) . . ?
C16 N2 H2 105(3) . . ?
C18 N2 H2 109(3) . . ?
C13 N2 H2 112(3) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 27(7) . . . . ?
O2 C1 C2 C3 -155(6) . . . . ?
C1 C2 C3 C4 31(18) . . . . ?
C2 C3 C4 C5 102(14) . . . . ?
C2 C3 C4 C9 -77(14) . . . . ?
C9 C4 C5 C6 0.6(5) . . . . ?
C3 C4 C5 C6 -178.8(3) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
C5 C6 C7 C10 -179.0(3) . . . . ?
C6 C7 C8 C9 0.1(6) . . . . ?
C10 C7 C8 C9 179.2(3) . . . . ?
C7 C8 C9 C4 0.0(6) . . . . ?
C5 C4 C9 C8 -0.3(6) . . . . ?
C3 C4 C9 C8 179.0(3) . . . . ?
C8 C7 C10 C11 -88(23) . . . . ?
C6 C7 C10 C11 91(23) . . . . ?
C7 C10 C11 C12 -99(26) . . . . ?
C10 C11 C12 O4 29(14) . . . . ?
C10 C11 C12 O3 -150(14) . . . . ?
N2 C13 C14 N1 -1.9(4) . . . . ?
N1 C15 C16 N2 -2.9(4) . . . . ?
N1 C17 C18 N2 -2.3(5) . . . . ?
C16 C15 N1 C14 62.8(4) . . . . ?
C16 C15 N1 C17 -58.5(4) . . . . ?
C13 C14 N1 C15 -59.9(4) . . . . ?
C13 C14 N1 C17 61.6(4) . . . . ?
C18 C17 N1 C15 61.7(4) . . . . ?
C18 C17 N1 C14 -59.2(4) . . . . ?
C15 C16 N2 C18 62.6(4) . . . . ?
C15 C16 N2 C13 -59.0(4) . . . . ?
C17 C18 N2 C16 -59.3(4) . . . . ?
C17 C18 N2 C13 62.3(4) . . . . ?
C14 C13 N2 C16 61.9(4) . . . . ?
C14 C13 N2 C18 -59.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.96(4) 1.65(4) 2.594(3) 169(4) 3_564
N2 H2 O2 0.94(5) 1.68(5) 2.602(4) 167(4) 3_666

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.92
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.062
_vrf_PLAT242_saro                
;
PROBLEM: Check Low Ueq as Compared to Neighbors for C1
RESPONSE: There might be a mild unresolved disorder for the
oxygens of one of the carboxylate groups which makes the thermal
parameters of C1 less than the neighbouring oxygens.
;


