Supplementary Material (ESI) for CrystEngComm This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name _publ_author_address 'Radu Custelcean' '' 'Maryna G. Gorbunova' '' _publ_contact_author_name 'Dr Radu Custelcean' _publ_contact_author_address ; Chemical Sciences Division Oak Ridge National Laboratory PO Box 2008 MS-6119 Oak Ridge Tennessee 37831-6119 UNITED STATES OF AMERICA ; _publ_contact_author_email CUSTELCEANR@ORNL.GOV _publ_section_title ; Protonation-Assisted Spontaneous Resolution: Formation of a Homochiral 2D Interpenetrated Hydrogen-Bonded Network from 4,4'-Binicotinic Acid under Highly Acidic Conditions ; data_c:\frames\026\work\026s _database_code_depnum_ccdc_archive 'CCDC 262787' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'binicotinic acid dihydrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 N2 O6' _chemical_formula_weight 280.24 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)/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 8.5479(8) _cell_length_b 15.9729(14) _cell_length_c 9.6655(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.722(2) _cell_angle_gamma 90.00 _cell_volume 1234.30(19) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9513 _exptl_absorpt_correction_T_max 0.9746 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15285 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 28.35 _reflns_number_total 3065 _reflns_number_gt 2788 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0670P)^2^+0.3043P] 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 3065 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 O3 O 0.96014(10) 0.12725(5) 0.84193(8) 0.02352(18) Uani 1 1 d . . . N2 N 0.72358(11) -0.02246(5) 1.14154(9) 0.01989(19) Uani 1 1 d . . . O2 O 0.55632(10) 0.14882(5) 0.73630(8) 0.02431(19) Uani 1 1 d . . . N1 N 0.74490(12) -0.02018(6) 0.42159(10) 0.0219(2) Uani 1 1 d . . . C8 C 0.80822(12) 0.05316(6) 0.96758(10) 0.0167(2) Uani 1 1 d . . . C1 C 0.69549(13) 0.05087(6) 0.46733(11) 0.0199(2) Uani 1 1 d . . . H1 H 0.6666 0.0970 0.4011 0.024 Uiso 1 1 calc R . . O1 O 0.61345(14) 0.19994(5) 0.54344(10) 0.0360(2) Uani 1 1 d . . . C12 C 0.90780(13) 0.12722(6) 0.94518(11) 0.0196(2) Uani 1 1 d . . . C6 C 0.61279(13) 0.14237(6) 0.63637(11) 0.0197(2) Uani 1 1 d . . . C3 C 0.73246(12) -0.00658(6) 0.70554(10) 0.0161(2) Uani 1 1 d . . . C2 C 0.68417(12) 0.06078(6) 0.60625(10) 0.0169(2) Uani 1 1 d . . . O4 O 0.93285(14) 0.18289(5) 1.04506(10) 0.0375(2) Uani 1 1 d . . . C10 C 0.65132(13) -0.07495(6) 0.89871(11) 0.0195(2) Uani 1 1 d . . . H10 H 0.5985 -0.1168 0.8277 0.023 Uiso 1 1 calc R . . C11 C 0.65023(13) -0.08120(6) 1.04121(11) 0.0216(2) Uani 1 1 d . . . H11 H 0.5970 -0.1275 1.0678 0.026 Uiso 1 1 calc R . . C5 C 0.78759(14) -0.08516(7) 0.51464(11) 0.0229(2) Uani 1 1 d . . . H5 H 0.8213 -0.1360 0.4825 0.027 Uiso 1 1 calc R . . C4 C 0.78403(13) -0.08043(6) 0.65677(11) 0.0204(2) Uani 1 1 d . . . H4 H 0.8166 -0.1274 0.7210 0.024 Uiso 1 1 calc R . . C9 C 0.73024(12) -0.00705(6) 0.85914(10) 0.01581(19) Uani 1 1 d . . . C7 C 0.80032(13) 0.04332(6) 1.10753(11) 0.0189(2) Uani 1 1 d . . . H7 H 0.8506 0.0843 1.1812 0.023 Uiso 1 1 calc R . . O6 O 0.05437(13) 0.24396(6) 0.66099(11) 0.0343(2) Uani 1 1 d . . . O5 O 0.89250(12) 0.21626(6) 0.34316(10) 0.0319(2) Uani 1 1 d . . . H6OA H 0.157(3) 0.2573(11) 0.714(2) 0.046(5) Uiso 1 1 d . . . H5OA H 0.936(3) 0.2239(12) 0.440(3) 0.058(6) Uiso 1 1 d . . . H6O H 0.020(3) 0.2134(13) 0.719(2) 0.058(6) Uiso 1 1 d . . . H2N H 0.730(2) -0.0285(13) 1.255(2) 0.058(6) Uiso 1 1 d . . . H5O H 0.952(3) 0.2489(14) 0.304(3) 0.066(6) Uiso 1 1 d . . . H1O H 0.530(3) 0.2582(16) 0.543(3) 0.089(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 O3 0.0273(4) 0.0249(4) 0.0210(4) -0.0012(3) 0.0119(3) -0.0059(3) N2 0.0257(4) 0.0219(4) 0.0142(4) 0.0019(3) 0.0098(3) 0.0020(3) O2 0.0314(4) 0.0240(4) 0.0203(4) 0.0016(3) 0.0126(3) 0.0073(3) N1 0.0277(4) 0.0248(4) 0.0145(4) -0.0009(3) 0.0091(3) 0.0008(3) C8 0.0204(4) 0.0161(4) 0.0143(4) 0.0001(3) 0.0068(4) 0.0001(3) C1 0.0248(5) 0.0211(5) 0.0139(4) 0.0021(3) 0.0069(4) 0.0006(4) O1 0.0602(6) 0.0229(4) 0.0359(5) 0.0137(3) 0.0308(5) 0.0163(4) C12 0.0238(5) 0.0180(4) 0.0162(4) -0.0002(3) 0.0060(4) -0.0028(4) C6 0.0232(5) 0.0184(5) 0.0171(4) 0.0019(3) 0.0065(4) 0.0032(3) C3 0.0185(4) 0.0179(4) 0.0116(4) -0.0002(3) 0.0051(3) -0.0005(3) C2 0.0193(4) 0.0170(4) 0.0144(4) 0.0003(3) 0.0059(3) 0.0005(3) O4 0.0653(6) 0.0261(4) 0.0296(4) -0.0126(3) 0.0271(4) -0.0217(4) C10 0.0246(5) 0.0173(4) 0.0165(5) -0.0006(3) 0.0071(4) -0.0024(4) C11 0.0279(5) 0.0195(5) 0.0198(5) 0.0023(4) 0.0115(4) -0.0016(4) C5 0.0298(5) 0.0223(5) 0.0173(5) -0.0018(4) 0.0094(4) 0.0048(4) C4 0.0276(5) 0.0185(5) 0.0146(4) 0.0009(3) 0.0069(4) 0.0040(4) C9 0.0190(4) 0.0160(4) 0.0126(4) 0.0010(3) 0.0057(3) 0.0021(3) C7 0.0230(4) 0.0196(4) 0.0145(4) -0.0017(3) 0.0072(4) -0.0001(4) O6 0.0361(5) 0.0385(5) 0.0292(5) 0.0068(4) 0.0127(4) -0.0034(4) O5 0.0398(5) 0.0304(4) 0.0281(5) 0.0012(3) 0.0152(4) 0.0021(4) _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 O3 C12 1.2297(12) . ? N2 C11 1.3355(14) . ? N2 C7 1.3397(13) . ? O2 C6 1.2274(12) . ? N1 C5 1.3368(14) . ? N1 C1 1.3393(13) . ? C8 C7 1.3869(13) . ? C8 C9 1.4048(13) . ? C8 C12 1.5169(13) . ? C1 C2 1.3890(13) . ? O1 C6 1.2868(13) . ? C12 O4 1.2737(13) . ? C6 C2 1.5104(13) . ? C3 C4 1.3982(13) . ? C3 C2 1.4031(13) . ? C3 C9 1.4915(13) . ? C10 C11 1.3843(13) . ? C10 C9 1.4001(13) . ? C5 C4 1.3868(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 C11 N2 C7 121.17(8) . . ? C5 N1 C1 118.60(9) . . ? C7 C8 C9 118.43(9) . . ? C7 C8 C12 116.81(8) . . ? C9 C8 C12 124.71(8) . . ? N1 C1 C2 123.62(9) . . ? O3 C12 O4 127.08(10) . . ? O3 C12 C8 119.99(9) . . ? O4 C12 C8 112.87(9) . . ? O2 C6 O1 126.12(9) . . ? O2 C6 C2 121.48(9) . . ? O1 C6 C2 112.35(9) . . ? C4 C3 C2 117.90(8) . . ? C4 C3 C9 116.61(8) . . ? C2 C3 C9 125.48(8) . . ? C1 C2 C3 118.01(9) . . ? C1 C2 C6 117.11(8) . . ? C3 C2 C6 124.82(8) . . ? C11 C10 C9 120.08(9) . . ? N2 C11 C10 120.34(9) . . ? N1 C5 C4 121.85(9) . . ? C5 C4 C3 120.00(9) . . ? C10 C9 C8 118.28(8) . . ? C10 C9 C3 116.92(8) . . ? C8 C9 C3 124.72(8) . . ? N2 C7 C8 121.69(9) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.461 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.050 data_022s _database_code_depnum_ccdc_archive 'CCDC 262788' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'binicotinic acid hydrochloride dihydrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 Cl N2 O6' _chemical_formula_weight 316.69 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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 10.665(6) _cell_length_b 6.222(3) _cell_length_c 11.579(6) _cell_angle_alpha 90.00 _cell_angle_beta 116.740(9) _cell_angle_gamma 90.00 _cell_volume 686.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.308 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9352 _exptl_absorpt_correction_T_max 0.9939 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5003 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1217 _reflns_number_gt 1088 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0529P)^2^+0.4543P] 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 1217 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _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 Cl1 Cl 0.7500 0.18403(14) 0.2500 0.0406(3) Uani 1 2 d S . . O1 O 1.0784(2) -0.1443(3) 0.00102(18) 0.0408(5) Uani 1 1 d . . . N1 N 1.3185(2) -0.6307(3) -0.01699(19) 0.0266(5) Uani 1 1 d . . . O2 O 1.06493(19) -0.2785(3) 0.17267(17) 0.0380(5) Uani 1 1 d . . . C2 C 1.2043(2) -0.4601(3) 0.0916(2) 0.0196(5) Uani 1 1 d . . . O3 O 0.9257(2) -0.2314(4) 0.3240(2) 0.0397(5) Uani 1 1 d . . . C6 C 1.1081(2) -0.2823(3) 0.0913(2) 0.0223(5) Uani 1 1 d . . . C1 C 1.2350(2) -0.4731(4) -0.0119(2) 0.0235(5) Uani 1 1 d . . . H1 H 1.1971 -0.3704 -0.0797 0.028 Uiso 1 1 calc R . . C5 C 1.3724(3) -0.7803(4) 0.0754(2) 0.0330(6) Uani 1 1 d . . . H5 H 1.4294 -0.8913 0.0678 0.040 Uiso 1 1 calc R . . C3 C 1.2631(2) -0.6110(3) 0.1917(2) 0.0207(5) Uani 1 1 d . . . C4 C 1.3464(3) -0.7749(4) 0.1805(2) 0.0297(6) Uani 1 1 d . . . H4 H 1.3846 -0.8820 0.2456 0.036 Uiso 1 1 calc R . . H1N H 1.340(3) -0.640(5) -0.086(3) 0.049(9) Uiso 1 1 d . . . H3O H 0.966(4) -0.254(6) 0.287(3) 0.051(11) Uiso 1 1 d . . . H3OA H 0.871(4) -0.119(8) 0.288(4) 0.086(14) Uiso 1 1 d . . . H1O H 1.0000 0.0000 0.0000 0.10(2) Uiso 1 2 d S . . 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 0.0657(7) 0.0287(5) 0.0431(6) 0.000 0.0384(5) 0.000 O1 0.0626(13) 0.0342(10) 0.0356(10) 0.0163(8) 0.0310(10) 0.0243(9) N1 0.0343(11) 0.0295(11) 0.0228(11) -0.0015(8) 0.0188(9) 0.0039(9) O2 0.0496(11) 0.0420(11) 0.0355(10) 0.0110(8) 0.0307(9) 0.0206(9) C2 0.0250(11) 0.0182(10) 0.0181(11) -0.0030(8) 0.0120(9) -0.0017(8) O3 0.0499(12) 0.0416(12) 0.0456(12) 0.0072(9) 0.0375(11) 0.0037(9) C6 0.0267(11) 0.0216(11) 0.0189(11) -0.0010(9) 0.0107(9) 0.0036(9) C1 0.0298(12) 0.0224(11) 0.0205(11) -0.0002(9) 0.0133(10) 0.0020(9) C5 0.0404(14) 0.0317(13) 0.0314(13) 0.0010(11) 0.0202(12) 0.0132(11) C3 0.0264(11) 0.0189(11) 0.0185(11) -0.0029(9) 0.0116(9) -0.0032(9) C4 0.0422(14) 0.0231(12) 0.0264(12) 0.0041(10) 0.0177(11) 0.0095(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 O1 C6 1.278(3) . ? N1 C5 1.337(3) . ? N1 C1 1.343(3) . ? O2 C6 1.221(3) . ? C2 C1 1.380(3) . ? C2 C3 1.401(3) . ? C2 C6 1.508(3) . ? C5 C4 1.365(4) . ? C3 C4 1.396(3) . ? C3 C3 1.498(4) 2_755 ? 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 C5 N1 C1 121.9(2) . . ? C1 C2 C3 119.1(2) . . ? C1 C2 C6 117.91(19) . . ? C3 C2 C6 123.00(19) . . ? O2 C6 O1 125.3(2) . . ? O2 C6 C2 120.3(2) . . ? O1 C6 C2 114.40(19) . . ? N1 C1 C2 120.1(2) . . ? N1 C5 C4 120.6(2) . . ? C4 C3 C2 118.7(2) . . ? C4 C3 C3 117.91(18) . 2_755 ? C2 C3 C3 123.39(18) . 2_755 ? C5 C4 C3 119.6(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.308 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.063 #=== END data_c:\frames\102\work\102s _database_code_depnum_ccdc_archive 'CCDC 262789' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'binicotinic acid dihydrochloride' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Cl2 N2 O4' _chemical_formula_weight 317.12 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 C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 12.9485(18) _cell_length_b 5.9793(8) _cell_length_c 8.6189(12) _cell_angle_alpha 90.00 _cell_angle_beta 96.160(2) _cell_angle_gamma 90.00 _cell_volume 663.45(16) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.503 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7978 _exptl_absorpt_correction_T_max 0.8164 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2231 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 28.28 _reflns_number_total 1537 _reflns_number_gt 1532 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0378P)^2^+0.3413P] 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 0.00(10) _refine_ls_number_reflns 1537 _refine_ls_number_parameters 94 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0243 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0637 _refine_ls_wR_factor_gt 0.0636 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.69316(2) 0.96131(6) 0.35077(3) 0.02144(10) Uani 1 1 d . . . O1 O 0.38498(7) 0.4582(2) 0.89539(11) 0.0226(2) Uani 1 1 d . . . O2 O 0.44462(11) 0.3674(2) 0.66832(15) 0.0321(3) Uani 1 1 d . . . C6 C 0.44242(10) 0.4888(3) 0.79577(15) 0.0201(3) Uani 1 1 d . . . N1 N 0.64235(10) 0.8872(2) 0.68290(15) 0.0228(3) Uani 1 1 d . . . C1 C 0.57874(11) 0.7112(3) 0.68235(16) 0.0209(3) Uani 1 1 d . . . H1 H 0.5738 0.6096 0.5971 0.025 Uiso 1 1 calc R . . C3 C 0.53268(10) 0.8219(2) 0.93304(16) 0.0172(3) Uani 1 1 d . . . C2 C 0.51997(10) 0.6758(3) 0.80505(15) 0.0175(3) Uani 1 1 d . . . C5 C 0.65719(11) 1.0293(3) 0.80297(18) 0.0233(3) Uani 1 1 d . . . H5 H 0.7037 1.1517 0.7999 0.028 Uiso 1 1 calc R . . C4 C 0.60390(11) 0.9954(3) 0.93181(16) 0.0224(3) Uani 1 1 d . . . H4 H 0.6161 1.0912 1.0198 0.027 Uiso 1 1 calc R . . H1N H 0.6732 0.9049 0.6039 0.028(5) Uiso 1 1 d R . . H2 H 0.4019 0.2492 0.6675 0.039(6) Uiso 1 1 d R . . 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 0.02470(15) 0.02069(18) 0.01969(14) 0.00084(16) 0.00581(10) 0.00052(16) O1 0.0252(4) 0.0211(5) 0.0226(4) -0.0004(6) 0.0073(3) -0.0042(6) O2 0.0392(7) 0.0312(7) 0.0279(6) -0.0120(5) 0.0122(5) -0.0145(5) C6 0.0197(5) 0.0224(9) 0.0180(5) -0.0011(6) 0.0014(4) 0.0010(6) N1 0.0197(5) 0.0296(7) 0.0200(6) 0.0050(5) 0.0069(4) 0.0016(5) C1 0.0200(6) 0.0258(9) 0.0170(6) 0.0001(5) 0.0027(5) 0.0017(6) C3 0.0179(6) 0.0174(8) 0.0169(6) 0.0025(5) 0.0049(5) 0.0021(5) C2 0.0173(6) 0.0176(7) 0.0179(6) 0.0004(5) 0.0028(4) 0.0015(5) C5 0.0197(6) 0.0218(8) 0.0292(8) 0.0041(5) 0.0062(5) -0.0015(5) C4 0.0228(6) 0.0224(10) 0.0225(6) -0.0019(6) 0.0052(5) -0.0029(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 O1 C6 1.2087(17) . ? O2 C6 1.3194(19) . ? C6 C2 1.499(2) . ? N1 C1 1.336(2) . ? N1 C5 1.337(2) . ? C1 C2 1.3838(18) . ? C3 C4 1.389(2) . ? C3 C2 1.4029(19) . ? C3 C3 1.503(3) 2_657 ? C5 C4 1.384(2) . ? 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 C6 O2 125.32(16) . . ? O1 C6 C2 122.31(14) . . ? O2 C6 C2 112.36(12) . . ? C1 N1 C5 122.73(13) . . ? N1 C1 C2 120.45(13) . . ? C4 C3 C2 118.75(12) . . ? C4 C3 C3 115.79(11) . 2_657 ? C2 C3 C3 125.15(12) . 2_657 ? C1 C2 C3 118.56(13) . . ? C1 C2 C6 119.55(12) . . ? C3 C2 C6 121.85(12) . . ? N1 C5 C4 119.05(14) . . ? C5 C4 C3 120.29(14) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.299 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.053 #=== END