Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        M.Grossel
_publ_contact_author_address     
;
Department of Chemistry
University of Southampton
Southampton
S017 1BJ
UNITED KINGDOM
;

_publ_contact_author_email       MCG1@SOTON.AC.UK

_publ_section_title              
;
Polymorphism in Pyridine-2,6-dicarboxylic acid:
Competition between Robust synthons
;
loop_
_publ_author_name
M.Grossel
'Andrew N. Dwyer'
M.Hursthouse
'James B. Orton'

# Attachment '4a.cif'

data_s97
_database_code_depnum_ccdc_archive 'CCDC 292208'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H4 N O4'
_chemical_formula_weight         166.11

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           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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                   14.034(10)
_cell_length_b                   13.205(17)
_cell_length_c                   3.699(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     685.5(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9946
_exptl_absorpt_correction_T_max  0.9986
_exptl_absorpt_process_details   'SORTAV Blessing (1997)'
_exptl_special_details           
;
PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
the entire data set is used to refine the cell, which is indexed from all
observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD Area Detector'
_diffrn_measurement_method       '\f and \w scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6128
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         27.46
_reflns_number_total             1543
_reflns_number_gt                1275
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement       
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1147P)^2^+0.0922P] where P=(Fo^2^+2Fc^2^)/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       0.047(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(2)
_refine_ls_number_reflns         1543
_refine_ls_number_parameters     114
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1701
_refine_ls_wR_factor_gt          0.1573
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.54510(17) 0.6683(2) 0.2644(8) 0.0251(6) Uani 1 1 d . . .
C2 C 0.45509(19) 0.7167(2) 0.1495(8) 0.0267(6) Uani 1 1 d . . .
C3 C 0.3828(2) 0.6560(2) 0.0160(8) 0.0325(7) Uani 1 1 d . . .
H3 H 0.3904 0.5846 0.0018 0.039 Uiso 1 1 calc R . .
C4 C 0.2990(2) 0.7020(2) -0.0967(9) 0.0314(7) Uani 1 1 d . . .
H4 H 0.2479 0.6619 -0.1859 0.038 Uiso 1 1 calc R . .
C5 C 0.28963(19) 0.8069(2) -0.0790(8) 0.0282(6) Uani 1 1 d . . .
H5 H 0.2326 0.8392 -0.1559 0.034 Uiso 1 1 calc R . .
C6 C 0.3653(2) 0.86308(18) 0.0534(8) 0.0260(6) Uani 1 1 d . . .
C7 C 0.35470(19) 0.97412(17) 0.0686(7) 0.0221(6) Uani 1 1 d . . .
N1 N 0.44881(19) 0.8209(2) 0.1756(7) 0.0379(7) Uani 1 1 d . . .
O1 O 0.55982(18) 0.58054(18) 0.1735(8) 0.0521(8) Uani 1 1 d . . .
O2 O 0.59981(17) 0.7194(2) 0.4487(7) 0.0459(7) Uani 1 1 d . . .
O3 O 0.41265(17) 1.02254(16) 0.2406(7) 0.0443(7) Uani 1 1 d . . .
O4 O 0.28698(18) 1.01218(17) -0.0939(8) 0.0482(6) Uani 1 1 d . . .
H1N H 0.507(2) 0.860(2) 0.328(9) 0.025(8) 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 0.0194(12) 0.0284(13) 0.0273(12) 0.0073(11) 0.0032(11) 0.0043(10)
C2 0.0229(13) 0.0338(14) 0.0234(13) 0.0055(13) 0.0020(11) 0.0012(10)
C3 0.0364(15) 0.0285(13) 0.0328(15) -0.0022(13) 0.0030(12) -0.0032(11)
C4 0.0272(14) 0.0382(15) 0.0289(14) -0.0067(14) -0.0012(13) -0.0065(11)
C5 0.0251(13) 0.0386(15) 0.0210(13) 0.0000(12) 0.0011(12) 0.0010(11)
C6 0.0301(13) 0.0269(13) 0.0209(11) -0.0020(11) 0.0044(11) 0.0006(10)
C7 0.0243(12) 0.0218(11) 0.0203(11) 0.0007(11) 0.0017(11) 0.0014(10)
N1 0.0372(14) 0.0444(15) 0.0321(15) 0.0004(13) 0.0001(11) -0.0058(11)
O1 0.0451(14) 0.0407(13) 0.070(2) 0.0094(13) 0.0035(13) 0.0132(10)
O2 0.0314(11) 0.0620(15) 0.0443(14) 0.0037(12) -0.0067(10) 0.0045(10)
O3 0.0451(13) 0.0336(12) 0.0541(15) -0.0060(11) 0.0007(13) -0.0045(10)
O4 0.0540(14) 0.0388(12) 0.0518(13) 0.0038(12) -0.0060(14) 0.0149(10)

_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 1.224(4) . ?
C1 O2 1.228(4) . ?
C1 C2 1.478(4) . ?
C2 N1 1.381(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.374(4) . ?
C6 C7 1.475(4) . ?
C7 O3 1.215(4) . ?
C7 O4 1.232(4) . ?
N1 H1N 1.12(3) . ?

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 124.5(3) . . ?
O1 C1 C2 118.3(3) . . ?
O2 C1 C2 117.1(3) . . ?
N1 C2 C3 123.7(3) . . ?
N1 C2 C1 117.7(2) . . ?
C3 C2 C1 118.5(3) . . ?
C2 C3 C4 118.3(3) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C5 123.6(2) . . ?
N1 C6 C7 118.5(3) . . ?
C5 C6 C7 117.9(3) . . ?
O3 C7 O4 123.9(2) . . ?
O3 C7 C6 118.4(3) . . ?
O4 C7 C6 117.7(3) . . ?
C6 N1 C2 115.8(2) . . ?
C6 N1 H1N 127.1(15) . . ?
C2 N1 H1N 116.5(15) . . ?

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 H1N O3 1.12(3) 2.45(3) 3.525(5) 160(2) 2_675
C3 H3 O1 0.95 2.59 3.465(5) 153.0 2_664
C4 H4 O4 0.95 2.54 3.335(5) 141.9 4_544
C5 H5 O2 0.95 2.49 3.205(4) 131.8 3_464

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.071

# Attachment '4b.cif'

data_s94
_database_code_depnum_ccdc_archive 'CCDC 292209'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H9 N O6'
_chemical_formula_weight         203.15

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   P2(1)/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                   3.65790(10)
_cell_length_b                   11.0577(4)
_cell_length_c                   21.5478(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.0200(10)
_cell_angle_gamma                90.00
_cell_volume                     870.35(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9545
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_process_details   'SORTAV Blessing (1997)'
_exptl_special_details           
;
PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
the entire data set is used to refine the cell, which is indexed from all
observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD Area Detector'
_diffrn_measurement_method       '\f and \w scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9977
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_sigmaI/netI    0.0744
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1969
_reflns_number_gt                1252
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement       
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         1969
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.7737(5) 0.25587(16) 0.47775(8) 0.0192(4) Uani 1 1 d . . .
C2 C 0.6046(5) 0.30963(16) 0.41926(9) 0.0184(4) Uani 1 1 d . . .
C3 C 0.5900(5) 0.43341(16) 0.40839(9) 0.0208(4) Uani 1 1 d . . .
H3 H 0.6840 0.4889 0.4389 0.025 Uiso 1 1 calc R . .
C4 C 0.4354(5) 0.47416(17) 0.35212(9) 0.0240(5) Uani 1 1 d . . .
H4 H 0.4278 0.5582 0.3430 0.029 Uiso 1 1 calc R . .
C5 C 0.2921(5) 0.39100(16) 0.30941(9) 0.0222(4) Uani 1 1 d . . .
H5 H 0.1849 0.4165 0.2705 0.027 Uiso 1 1 calc R . .
C6 C 0.3096(5) 0.26915(16) 0.32511(9) 0.0197(4) Uani 1 1 d . . .
C7 C 0.1393(5) 0.17513(17) 0.28242(10) 0.0236(4) Uani 1 1 d . . .
N1 N 0.4663(4) 0.22822(12) 0.37820(7) 0.0185(4) Uani 1 1 d . . .
O1 O 0.8888(4) 0.33640(11) 0.51891(6) 0.0264(3) Uani 1 1 d . . .
H1O H 0.9778 0.3011 0.5507 0.040 Uiso 1 1 calc R . .
O2 O 0.8008(4) 0.14678(11) 0.48553(6) 0.0256(3) Uani 1 1 d . . .
O3 O 0.1490(4) 0.06145(11) 0.30146(7) 0.0301(4) Uani 1 1 d . . .
H3O H 0.2532 0.0578 0.3371 0.045 Uiso 1 1 calc R . .
O4 O -0.0127(4) 0.20156(13) 0.23278(6) 0.0308(4) Uani 1 1 d . . .
O1W O 0.4469(4) -0.02963(13) 0.40792(7) 0.0289(4) Uani 1 1 d . . .
H1W1 H 0.565(8) 0.036(3) 0.4307(14) 0.073(9) Uiso 1 1 d . . .
H1W2 H 0.112(8) 0.251(2) 0.1506(15) 0.058(9) Uiso 1 1 d . . .
O2W O 0.1966(4) 0.25873(15) 0.11535(8) 0.0321(4) Uani 1 1 d . . .
H2W1 H 0.303(8) -0.062(3) 0.4348(15) 0.074(10) Uiso 1 1 d . . .
H2W2 H 0.282(7) 0.335(2) 0.1115(12) 0.051(8) 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 0.0180(10) 0.0230(11) 0.0166(11) -0.0026(8) 0.0021(7) -0.0034(7)
C2 0.0145(9) 0.0237(10) 0.0170(11) 0.0004(8) 0.0022(7) -0.0007(6)
C3 0.0188(10) 0.0207(10) 0.0232(11) -0.0030(8) 0.0020(7) -0.0031(7)
C4 0.0236(10) 0.0190(10) 0.0294(12) 0.0035(8) 0.0006(8) 0.0012(7)
C5 0.0201(10) 0.0277(11) 0.0187(11) 0.0056(8) -0.0007(7) 0.0021(7)
C6 0.0166(10) 0.0250(10) 0.0175(11) -0.0011(8) 0.0004(7) -0.0003(7)
C7 0.0212(11) 0.0304(11) 0.0193(12) -0.0011(9) 0.0014(8) 0.0002(8)
N1 0.0176(8) 0.0215(8) 0.0166(9) -0.0012(7) 0.0012(6) -0.0015(6)
O1 0.0345(8) 0.0255(7) 0.0183(8) 0.0000(6) -0.0078(6) -0.0022(5)
O2 0.0356(8) 0.0189(7) 0.0217(8) 0.0013(6) -0.0041(6) -0.0015(5)
O3 0.0413(9) 0.0241(8) 0.0240(9) -0.0036(6) -0.0074(6) -0.0043(6)
O4 0.0331(9) 0.0403(9) 0.0179(9) 0.0002(6) -0.0070(6) -0.0024(6)
O1W 0.0386(9) 0.0223(8) 0.0254(9) 0.0002(7) -0.0014(7) -0.0031(6)
O2W 0.0422(9) 0.0327(9) 0.0210(10) 0.0008(7) -0.0015(7) -0.0070(6)

_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 1.221(2) . ?
C1 O1 1.311(2) . ?
C1 C2 1.497(3) . ?
C2 N1 1.342(2) . ?
C2 C3 1.389(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.332(2) . ?
C6 C7 1.502(3) . ?
C7 O4 1.215(2) . ?
C7 O3 1.322(2) . ?
O1 H1O 0.8400 . ?
O3 H3O 0.8400 . ?
O1W H1W1 0.96(3) . ?
O1W H2W1 0.88(3) . ?
O2W H1W2 0.84(3) . ?
O2W H2W2 0.90(3) . ?

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 123.87(17) . . ?
O2 C1 C2 122.33(16) . . ?
O1 C1 C2 113.80(15) . . ?
N1 C2 C3 122.67(17) . . ?
N1 C2 C1 114.40(15) . . ?
C3 C2 C1 122.93(16) . . ?
C4 C3 C2 118.56(17) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 119.24(17) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 118.12(17) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 123.42(16) . . ?
N1 C6 C7 115.91(16) . . ?
C5 C6 C7 120.65(17) . . ?
O4 C7 O3 120.37(17) . . ?
O4 C7 C6 121.92(17) . . ?
O3 C7 C6 117.68(17) . . ?
C6 N1 C2 117.95(15) . . ?
C1 O1 H1O 109.5 . . ?
C7 O3 H3O 109.5 . . ?
H1W1 O1W H2W1 104(2) . . ?
H1W2 O2W H2W2 109(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
O3 H3O O1W 0.84 1.91 2.6835(19) 152.4 .
O1 H1O O2W 0.84 1.70 2.539(2) 173.5 4_666
O1W H1W1 O2 0.96(3) 1.88(3) 2.8372(19) 171(2) .
O1W H2W1 O2 0.88(3) 2.01(3) 2.827(2) 154(3) 3_656
O2W H2W2 O1W 0.90(3) 1.86(3) 2.738(2) 165(2) 2_655
O2W H1W2 O4 0.84(3) 1.93(3) 2.755(2) 167(3) .

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.059

# Attachment '6.cif'

data_s93
_database_code_depnum_ccdc_archive 'CCDC 292210'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 Cl N O5'
_chemical_formula_weight         219.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   5.1793(2)
_cell_length_b                   9.4760(3)
_cell_length_c                   8.5004(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.289(2)
_cell_angle_gamma                90.00
_cell_volume                     416.02(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.454
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9147
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_process_details   'SORTAV Blessing (1997)'
_exptl_special_details           
;
PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
the entire data set is used to refine the cell, which is indexed from all
observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD Area Detector'
_diffrn_measurement_method       '\f and \w scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5401
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1880
_reflns_number_gt                1821
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement       
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0555P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.28(5)
_refine_ls_number_reflns         1880
_refine_ls_number_parameters     138
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
Cl1 Cl 0.53151(7) -1.80230(5) -1.03897(5) 0.02043(13) Uani 1 1 d . . .
C5 C 0.1930(4) -1.6892(2) -0.8480(3) 0.0166(4) Uani 1 1 d . . .
H5 H 0.2521 -1.5991 -0.8784 0.020 Uiso 1 1 calc R . .
C3 C 0.2088(4) -1.9410(2) -0.8572(3) 0.0150(4) Uani 1 1 d . . .
H3 H 0.2781 -2.0263 -0.8949 0.018 Uiso 1 1 calc R . .
N1 N -0.0899(3) -1.82589(16) -0.69506(16) 0.0147(3) Uani 1 1 d . . .
O2 O -0.2625(3) -2.09154(16) -0.61441(18) 0.0246(3) Uani 1 1 d . . .
O1 O 0.0377(3) -2.18815(14) -0.75790(18) 0.0236(4) Uani 1 1 d . . .
H1 H -0.0317 -2.2644 -0.7336 0.035 Uiso 1 1 calc R . .
O4 O -0.0410(3) -1.45545(15) -0.73571(19) 0.0251(3) Uani 1 1 d . . .
C6 C -0.0004(4) -1.7023(2) -0.7445(2) 0.0144(4) Uani 1 1 d . . .
O3 O -0.3035(3) -1.58318(14) -0.59499(17) 0.0230(3) Uani 1 1 d . . .
H3A H -0.3656 -1.5038 -0.5752 0.034 Uiso 1 1 calc R . .
C4 C 0.2964(3) -1.8109(2) -0.90530(17) 0.0159(3) Uani 1 1 d . . .
C7 C -0.1197(4) -1.56798(18) -0.6887(3) 0.0151(4) Uani 1 1 d . . .
C2 C 0.0159(4) -1.9422(2) -0.7518(2) 0.0155(4) Uani 1 1 d . . .
C1 C -0.0868(4) -2.08161(18) -0.6984(2) 0.0149(4) Uani 1 1 d . . .
O1W O -0.4877(3) -2.35122(19) -0.52141(19) 0.0289(4) Uani 1 1 d . . .
H1WB H -0.605(5) -2.347(4) -0.467(3) 0.042(8) Uiso 1 1 d . . .
H1WA H -0.420(6) -2.254(4) -0.547(3) 0.050(9) 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
Cl1 0.0201(2) 0.0190(2) 0.0237(2) 0.00200(18) 0.01195(15) -0.0013(2)
C5 0.0195(10) 0.0116(8) 0.0187(10) 0.0017(7) 0.0011(8) -0.0038(7)
C3 0.0168(10) 0.0101(8) 0.0189(10) -0.0010(7) 0.0063(8) 0.0008(7)
N1 0.0173(6) 0.0103(7) 0.0169(6) -0.0003(6) 0.0036(5) 0.0005(6)
O2 0.0294(8) 0.0128(7) 0.0341(8) 0.0014(6) 0.0187(6) -0.0013(6)
O1 0.0321(9) 0.0079(6) 0.0329(9) 0.0013(6) 0.0166(7) -0.0010(6)
O4 0.0315(8) 0.0112(7) 0.0346(9) -0.0001(6) 0.0165(7) 0.0003(6)
C6 0.0167(10) 0.0133(8) 0.0137(10) -0.0004(7) 0.0036(7) 0.0004(7)
O3 0.0270(7) 0.0111(7) 0.0329(8) -0.0009(6) 0.0155(6) 0.0024(6)
C4 0.0158(7) 0.0172(9) 0.0152(7) 0.0015(8) 0.0058(6) 0.0007(9)
C7 0.0171(9) 0.0114(10) 0.0171(9) -0.0013(7) 0.0024(7) -0.0012(7)
C2 0.0167(10) 0.0096(8) 0.0200(11) 0.0022(7) 0.0010(8) -0.0005(7)
C1 0.0177(9) 0.0089(9) 0.0186(9) -0.0021(8) 0.0053(7) 0.0011(7)
O1W 0.0329(8) 0.0131(8) 0.0443(9) 0.0006(6) 0.0262(7) 0.0012(6)

_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
Cl1 C4 1.7282(16) . ?
C5 C4 1.376(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C3 C4 1.386(3) . ?
C3 C2 1.391(3) . ?
C3 H3 0.9500 . ?
N1 C2 1.337(2) . ?
N1 C6 1.339(2) . ?
O2 C1 1.202(2) . ?
O1 C1 1.319(2) . ?
O1 H1 0.8400 . ?
O4 C7 1.220(2) . ?
C6 C7 1.506(3) . ?
O3 C7 1.295(3) . ?
O3 H3A 0.8400 . ?
C2 C1 1.506(3) . ?
O1W H1WB 0.79(3) . ?
O1W H1WA 1.01(4) . ?

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
C4 C5 C6 117.96(16) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C4 C3 C2 117.68(18) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C2 N1 C6 116.58(14) . . ?
C1 O1 H1 109.5 . . ?
N1 C6 C5 124.07(17) . . ?
N1 C6 C7 118.72(17) . . ?
C5 C6 C7 117.19(17) . . ?
C7 O3 H3A 109.5 . . ?
C5 C4 C3 119.74(14) . . ?
C5 C4 Cl1 120.37(14) . . ?
C3 C4 Cl1 119.89(14) . . ?
O4 C7 O3 125.3(2) . . ?
O4 C7 C6 118.7(2) . . ?
O3 C7 C6 115.95(16) . . ?
N1 C2 C3 123.96(17) . . ?
N1 C2 C1 116.81(17) . . ?
C3 C2 C1 119.23(17) . . ?
O2 C1 O1 125.56(18) . . ?
O2 C1 C2 123.21(17) . . ?
O1 C1 C2 111.22(18) . . ?
H1WB O1W H1WA 112(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 O4 0.84 1.81 2.5747(17) 150.3 1_545
O3 H3A O1W 0.84 1.66 2.494(2) 175.4 1_565
O1W H1WB N1 0.79(3) 2.19(3) 2.972(2) 175(3) 2_444
O1W H1WB O2 0.79(3) 2.53(3) 2.901(2) 111(3) 2_444
O1W H1WA O1 1.01(4) 3.14(3) 3.828(2) 126(2) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.057


