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