# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(I)-CCDC963007 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminobenzoic acid + 2-acetaminopyridine ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C7 H7 N O2, C7 H8 N2 O' _chemical_formula_sum 'C14 H15 N3 O3' _chemical_formula_weight 273.29 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 Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 14.8642(11) _cell_length_b 18.5544(15) _cell_length_c 4.7094(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1298.84(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12991 _cell_measurement_theta_min 1.76 _cell_measurement_theta_max 25.21 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9831 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Bruker Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12991 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.21 _reflns_number_total 2330 _reflns_number_gt 2032 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0439P)^2^+0.0661P] 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 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration unknown _refine_ls_number_reflns 2330 _refine_ls_number_parameters 198 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0788 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 O2A O 0.32546(8) 0.69922(6) 0.4111(3) 0.0296(3) Uani 1 1 d . . . O1A O 0.36752(9) 0.58407(7) 0.3611(3) 0.0305(3) Uani 1 1 d . . . N1B N 0.48608(10) 0.63021(8) -0.0343(3) 0.0265(4) Uani 1 1 d . . . N2B N 0.43294(10) 0.74616(8) -0.0557(4) 0.0269(4) Uani 1 1 d . . . N1A N 0.04776(11) 0.54845(11) 1.2534(4) 0.0329(4) Uani 1 1 d . . . H4 H 0.0252(17) 0.5849(14) 1.391(6) 0.064(8) Uiso 1 1 d . . . H2 H 0.3992(15) 0.7308(11) 0.092(6) 0.044(6) Uiso 1 1 d . . . H3 H 0.0496(13) 0.5027(13) 1.336(5) 0.045(7) Uiso 1 1 d . . . H1 H 0.4066(18) 0.6057(16) 0.219(7) 0.082(9) Uiso 1 1 d . . . C4 C 0.31709(11) 0.63573(9) 0.4776(4) 0.0242(4) Uani 1 1 d . . . C5 C 0.20074(13) 0.66134(10) 0.8354(4) 0.0280(4) Uani 1 1 d . . . H5 H 0.2115 0.7112 0.8033 0.034 Uiso 1 1 calc R . . O1B O 0.44885(10) 0.83851(8) -0.3756(3) 0.0382(4) Uani 1 1 d . . . C8 C 0.25165(12) 0.61050(10) 0.6877(4) 0.0228(4) Uani 1 1 d . . . C9 C 0.11770(12) 0.56819(10) 1.0772(4) 0.0265(4) Uani 1 1 d . . . C10 C 0.16975(12) 0.51704(10) 0.9337(4) 0.0277(4) Uani 1 1 d . . . H10 H 0.1598 0.4672 0.9682 0.033 Uiso 1 1 calc R . . C11 C 0.55513(13) 0.70804(11) -0.3782(5) 0.0328(5) Uani 1 1 d . . . H11 H 0.5583 0.7538 -0.4679 0.039 Uiso 1 1 calc R . . C13 C 0.13544(13) 0.64112(10) 1.0260(4) 0.0283(5) Uani 1 1 d . . . H13 H 0.1020 0.6770 1.1240 0.034 Uiso 1 1 calc R . . C14 C 0.41185(13) 0.81201(10) -0.1676(4) 0.0298(5) Uani 1 1 d . . . C15 C 0.49311(12) 0.69476(10) -0.1616(4) 0.0250(4) Uani 1 1 d . . . C16 C 0.23504(12) 0.53761(10) 0.7435(4) 0.0258(4) Uani 1 1 d . . . H16 H 0.2694 0.5018 0.6484 0.031 Uiso 1 1 calc R . . C17 C 0.60647(13) 0.58596(11) -0.3260(5) 0.0335(5) Uani 1 1 d . . . H17 H 0.6453 0.5475 -0.3777 0.040 Uiso 1 1 calc R . . C18 C 0.54247(13) 0.57790(10) -0.1165(5) 0.0303(5) Uani 1 1 d . . . H18 H 0.5381 0.5324 -0.0248 0.036 Uiso 1 1 calc R . . C19 C 0.33736(14) 0.84953(11) -0.0133(5) 0.0378(5) Uani 1 1 d . . . H19A H 0.3506 0.9012 -0.0016 0.057 Uiso 1 1 calc R . . H19B H 0.3320 0.8296 0.1787 0.057 Uiso 1 1 calc R . . H19C H 0.2807 0.8424 -0.1159 0.057 Uiso 1 1 calc R . . C20 C 0.61175(13) 0.65255(11) -0.4580(5) 0.0355(5) Uani 1 1 d . . . H20 H 0.6546 0.6601 -0.6045 0.043 Uiso 1 1 calc 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 O2A 0.0341(7) 0.0235(7) 0.0311(8) 0.0017(6) 0.0019(6) -0.0021(5) O1A 0.0338(7) 0.0257(7) 0.0321(8) 0.0038(6) 0.0071(7) 0.0031(6) N1B 0.0284(8) 0.0246(8) 0.0266(9) 0.0008(7) -0.0001(8) 0.0000(6) N2B 0.0300(8) 0.0260(8) 0.0248(9) 0.0025(7) 0.0019(8) 0.0012(7) N1A 0.0307(9) 0.0374(10) 0.0307(10) 0.0017(9) 0.0068(8) -0.0027(8) C4 0.0230(9) 0.0274(10) 0.0223(11) -0.0018(8) -0.0062(8) -0.0005(8) C5 0.0303(10) 0.0246(9) 0.0290(11) 0.0000(9) -0.0039(9) 0.0006(8) O1B 0.0420(8) 0.0367(8) 0.0359(9) 0.0131(7) -0.0011(7) -0.0018(6) C8 0.0219(9) 0.0248(9) 0.0217(10) 0.0013(8) -0.0041(8) 0.0003(7) C9 0.0242(10) 0.0318(10) 0.0234(10) 0.0019(8) -0.0053(9) -0.0005(8) C10 0.0310(10) 0.0244(9) 0.0278(11) 0.0025(9) -0.0024(9) -0.0019(8) C11 0.0332(11) 0.0348(10) 0.0303(11) 0.0045(9) 0.0019(10) -0.0059(9) C13 0.0271(10) 0.0290(10) 0.0289(12) -0.0047(8) -0.0003(9) 0.0036(8) C14 0.0309(10) 0.0277(10) 0.0306(11) 0.0037(9) -0.0087(10) -0.0025(8) C15 0.0250(9) 0.0279(10) 0.0220(10) -0.0026(8) -0.0028(8) -0.0027(8) C16 0.0274(10) 0.0244(10) 0.0254(10) -0.0005(8) -0.0008(9) 0.0033(8) C17 0.0308(10) 0.0342(11) 0.0355(13) -0.0060(10) 0.0012(10) 0.0014(9) C18 0.0327(10) 0.0276(10) 0.0306(12) -0.0012(9) -0.0003(10) -0.0003(8) C19 0.0418(12) 0.0297(10) 0.0418(14) 0.0030(10) -0.0019(11) 0.0045(9) C20 0.0300(11) 0.0443(12) 0.0323(12) -0.0031(9) 0.0071(10) -0.0057(9) _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 O2A C4 1.225(2) . ? O1A C4 1.335(2) . ? O1A H1 0.97(3) . ? N1B C18 1.340(2) . ? N1B C15 1.343(2) . ? N2B C14 1.367(2) . ? N2B C15 1.399(2) . ? N2B H2 0.90(2) . ? N1A C9 1.380(3) . ? N1A H4 1.00(3) . ? N1A H3 0.93(3) . ? C4 C8 1.465(3) . ? C5 C13 1.374(3) . ? C5 C8 1.395(3) . ? C5 H5 0.9500 . ? O1B C14 1.226(2) . ? C8 C16 1.400(3) . ? C9 C10 1.399(3) . ? C9 C13 1.399(2) . ? C10 C16 1.375(3) . ? C10 H10 0.9500 . ? C11 C20 1.382(3) . ? C11 C15 1.397(3) . ? C11 H11 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.496(3) . ? C16 H16 0.9500 . ? C17 C18 1.379(3) . ? C17 C20 1.385(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20 0.9500 . ? 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 O1A H1 108.8(17) . . ? C18 N1B C15 117.93(16) . . ? C14 N2B C15 128.20(18) . . ? C14 N2B H2 116.8(14) . . ? C15 N2B H2 114.5(14) . . ? C9 N1A H4 117.7(15) . . ? C9 N1A H3 118.0(13) . . ? H4 N1A H3 111(2) . . ? O2A C4 O1A 121.89(17) . . ? O2A C4 C8 123.20(16) . . ? O1A C4 C8 114.91(15) . . ? C13 C5 C8 121.61(17) . . ? C13 C5 H5 119.2 . . ? C8 C5 H5 119.2 . . ? C5 C8 C16 117.66(17) . . ? C5 C8 C4 118.75(16) . . ? C16 C8 C4 123.56(17) . . ? N1A C9 C10 121.81(17) . . ? N1A C9 C13 120.15(18) . . ? C10 C9 C13 117.95(17) . . ? C16 C10 C9 121.12(17) . . ? C16 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C20 C11 C15 117.98(19) . . ? C20 C11 H11 121.0 . . ? C15 C11 H11 121.0 . . ? C5 C13 C9 120.63(18) . . ? C5 C13 H13 119.7 . . ? C9 C13 H13 119.7 . . ? O1B C14 N2B 124.30(18) . . ? O1B C14 C19 122.22(17) . . ? N2B C14 C19 113.48(18) . . ? N1B C15 C11 122.31(17) . . ? N1B C15 N2B 113.51(17) . . ? C11 C15 N2B 124.18(18) . . ? C10 C16 C8 121.00(17) . . ? C10 C16 H16 119.5 . . ? C8 C16 H16 119.5 . . ? C18 C17 C20 117.20(18) . . ? C18 C17 H17 121.4 . . ? C20 C17 H17 121.4 . . ? N1B C18 C17 124.04(18) . . ? N1B C18 H18 118.0 . . ? C17 C18 H18 118.0 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C11 C20 C17 120.5(2) . . ? C11 C20 H20 119.7 . . ? C17 C20 H20 119.7 . . ? 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 C13 C5 C8 C16 -1.0(3) . . . . ? C13 C5 C8 C4 177.07(17) . . . . ? O2A C4 C8 C5 -4.9(3) . . . . ? O1A C4 C8 C5 175.33(16) . . . . ? O2A C4 C8 C16 173.06(18) . . . . ? O1A C4 C8 C16 -6.7(3) . . . . ? N1A C9 C10 C16 175.36(19) . . . . ? C13 C9 C10 C16 -1.4(3) . . . . ? C8 C5 C13 C9 -0.3(3) . . . . ? N1A C9 C13 C5 -175.35(18) . . . . ? C10 C9 C13 C5 1.5(3) . . . . ? C15 N2B C14 O1B -5.4(3) . . . . ? C15 N2B C14 C19 173.97(18) . . . . ? C18 N1B C15 C11 1.5(3) . . . . ? C18 N1B C15 N2B -178.40(16) . . . . ? C20 C11 C15 N1B -1.2(3) . . . . ? C20 C11 C15 N2B 178.75(19) . . . . ? C14 N2B C15 N1B -167.77(17) . . . . ? C14 N2B C15 C11 12.3(3) . . . . ? C9 C10 C16 C8 0.1(3) . . . . ? C5 C8 C16 C10 1.1(3) . . . . ? C4 C8 C16 C10 -176.89(18) . . . . ? C15 N1B C18 C17 -0.9(3) . . . . ? C20 C17 C18 N1B -0.2(3) . . . . ? C15 C11 C20 C17 0.1(3) . . . . ? C18 C17 C20 C11 0.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.21 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.121 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 963007' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(II)-CCDC963008 _audit_creation_method SHELXL-97 _chemical_name_systematic ; benzoic acid + 2-acetaminopyridine ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C7 H6 O2, C7 H8 N2 O' _chemical_formula_sum 'C14 H14 N2 O3' _chemical_formula_weight 258.27 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 12.776(3) _cell_length_b 5.1844(10) _cell_length_c 19.547(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.08(3) _cell_angle_gamma 90.00 _cell_volume 1261.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4851 _cell_measurement_theta_min 4.07 _cell_measurement_theta_max 27.84 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9856 _exptl_absorpt_correction_T_max 0.9884 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4851 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 27.84 _reflns_number_total 2852 _reflns_number_gt 1873 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0604P)^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 SHELXL _refine_ls_extinction_coef 0.015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2852 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _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 O1A O 0.43551(7) 0.57041(19) 0.25080(5) 0.0276(3) Uani 1 1 d . . . O2A O 0.60487(7) 0.48583(18) 0.30813(5) 0.0263(3) Uani 1 1 d . . . C6 C 0.52754(10) 0.4460(3) 0.25922(7) 0.0213(3) Uani 1 1 d . . . C8 C 0.53289(12) -0.1138(3) 0.09999(8) 0.0262(3) Uani 1 1 d . . . H8 H 0.5341 -0.2398 0.0649 0.031 Uiso 1 1 calc R . . C9 C 0.61273(11) 0.0755(3) 0.21148(8) 0.0240(3) Uani 1 1 d . . . H9 H 0.6692 0.0804 0.2525 0.029 Uiso 1 1 calc R . . C10 C 0.52880(10) 0.2504(2) 0.20345(7) 0.0201(3) Uani 1 1 d . . . C11 C 0.44652(11) 0.2433(2) 0.14274(7) 0.0235(3) Uani 1 1 d . . . H11 H 0.3887 0.3625 0.1369 0.028 Uiso 1 1 calc R . . C14 C 0.44916(11) 0.0622(3) 0.09096(8) 0.0257(3) Uani 1 1 d . . . H14 H 0.3937 0.0588 0.0494 0.031 Uiso 1 1 calc R . . C18 C 0.61442(12) -0.1064(3) 0.15983(8) 0.0273(4) Uani 1 1 d . . . H18 H 0.6719 -0.2265 0.1656 0.033 Uiso 1 1 calc R . . N1B N 0.41912(9) 0.9339(2) 0.34019(6) 0.0219(3) Uani 1 1 d . . . O1B O 0.69765(8) 1.20788(18) 0.48002(5) 0.0300(3) Uani 1 1 d . . . C5 C 0.49318(10) 1.0449(2) 0.39106(7) 0.0200(3) Uani 1 1 d . . . N2B N 0.59411(9) 0.9294(2) 0.40190(6) 0.0222(3) Uani 1 1 d . . . H2 H 0.5954(12) 0.786(3) 0.3751(9) 0.032(4) Uiso 1 1 d . . . C12 C 0.31822(11) 1.0267(3) 0.32596(8) 0.0251(3) Uani 1 1 d . . . H12 H 0.2660 0.9461 0.2900 0.030 Uiso 1 1 calc R . . C13 C 0.28712(12) 1.2324(3) 0.36095(8) 0.0247(3) Uani 1 1 d . . . H13 H 0.2151 1.2933 0.3498 0.030 Uiso 1 1 calc R . . C15 C 0.46814(12) 1.2549(3) 0.42888(8) 0.0264(4) Uani 1 1 d . . . H15 H 0.5215 1.3325 0.4648 0.032 Uiso 1 1 calc R . . C16 C 0.68866(11) 1.0114(2) 0.44441(7) 0.0219(3) Uani 1 1 d . . . C17 C 0.78219(11) 0.8368(3) 0.44344(8) 0.0269(4) Uani 1 1 d . . . H17A H 0.8055 0.8614 0.3995 0.040 Uiso 1 1 calc R . . H17B H 0.7604 0.6569 0.4470 0.040 Uiso 1 1 calc R . . H17C H 0.8416 0.8781 0.4833 0.040 Uiso 1 1 calc R . . C19 C 0.36441(11) 1.3478(3) 0.41314(8) 0.0269(4) Uani 1 1 d . . . H19 H 0.3458 1.4915 0.4382 0.032 Uiso 1 1 calc R . . H3 H 0.4383(16) 0.717(4) 0.2895(12) 0.071(6) 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 O1A 0.0208(6) 0.0326(6) 0.0276(6) -0.0099(5) 0.0016(4) 0.0028(4) O2A 0.0243(6) 0.0298(6) 0.0216(5) -0.0043(4) -0.0016(5) 0.0010(4) C6 0.0206(8) 0.0221(7) 0.0214(7) 0.0002(6) 0.0052(6) -0.0017(5) C8 0.0310(8) 0.0243(7) 0.0246(8) -0.0051(6) 0.0091(7) -0.0039(6) C9 0.0233(7) 0.0261(7) 0.0212(8) 0.0002(6) 0.0018(6) 0.0001(6) C10 0.0212(7) 0.0200(7) 0.0199(7) 0.0001(5) 0.0060(6) -0.0038(5) C11 0.0214(8) 0.0245(7) 0.0241(8) -0.0013(6) 0.0044(6) -0.0007(6) C14 0.0253(8) 0.0300(8) 0.0207(8) -0.0031(6) 0.0026(6) -0.0045(6) C18 0.0290(8) 0.0231(7) 0.0301(9) 0.0000(6) 0.0072(7) 0.0035(6) N1B 0.0212(6) 0.0230(6) 0.0207(6) -0.0030(5) 0.0031(5) -0.0004(5) O1B 0.0268(6) 0.0275(5) 0.0331(6) -0.0095(5) 0.0012(5) -0.0003(4) C5 0.0201(7) 0.0212(7) 0.0184(7) 0.0015(6) 0.0039(6) -0.0003(5) N2B 0.0220(7) 0.0213(6) 0.0218(7) -0.0058(5) 0.0016(5) 0.0013(5) C12 0.0214(8) 0.0283(8) 0.0241(8) -0.0036(6) 0.0021(6) -0.0014(6) C13 0.0214(7) 0.0286(8) 0.0243(8) 0.0002(6) 0.0055(6) 0.0027(6) C15 0.0244(8) 0.0277(8) 0.0251(8) -0.0080(6) 0.0015(6) 0.0001(6) C16 0.0221(8) 0.0222(7) 0.0205(7) 0.0017(6) 0.0029(6) -0.0021(5) C17 0.0230(8) 0.0251(7) 0.0311(9) 0.0003(6) 0.0032(7) 0.0013(6) C19 0.0277(8) 0.0266(7) 0.0267(8) -0.0050(6) 0.0071(6) 0.0020(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 O1A C6 1.3183(16) . ? O1A H3 1.07(2) . ? O2A C6 1.2269(16) . ? C6 C10 1.4918(19) . ? C8 C18 1.380(2) . ? C8 C14 1.387(2) . ? C8 H8 0.9500 . ? C9 C18 1.385(2) . ? C9 C10 1.3856(19) . ? C9 H9 0.9500 . ? C10 C11 1.396(2) . ? C11 C14 1.3863(19) . ? C11 H11 0.9500 . ? C14 H14 0.9500 . ? C18 H18 0.9500 . ? N1B C5 1.3377(18) . ? N1B C12 1.3446(18) . ? O1B C16 1.2243(16) . ? C5 C15 1.3934(19) . ? C5 N2B 1.3938(17) . ? N2B C16 1.3695(18) . ? N2B H2 0.913(16) . ? C12 C13 1.3733(19) . ? C12 H12 0.9500 . ? C13 C19 1.385(2) . ? C13 H13 0.9500 . ? C15 C19 1.378(2) . ? C15 H15 0.9500 . ? C16 C17 1.5027(19) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C19 H19 0.9500 . ? 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 C6 O1A H3 112.0(11) . . ? O2A C6 O1A 123.57(13) . . ? O2A C6 C10 122.95(12) . . ? O1A C6 C10 113.47(12) . . ? C18 C8 C14 120.14(14) . . ? C18 C8 H8 119.9 . . ? C14 C8 H8 119.9 . . ? C18 C9 C10 120.14(13) . . ? C18 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C11 119.57(13) . . ? C9 C10 C6 119.87(12) . . ? C11 C10 C6 120.56(12) . . ? C14 C11 C10 120.02(13) . . ? C14 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C14 C8 119.88(14) . . ? C11 C14 H14 120.1 . . ? C8 C14 H14 120.1 . . ? C8 C18 C9 120.24(14) . . ? C8 C18 H18 119.9 . . ? C9 C18 H18 119.9 . . ? C5 N1B C12 118.92(12) . . ? N1B C5 C15 121.46(12) . . ? N1B C5 N2B 113.74(12) . . ? C15 C5 N2B 124.79(12) . . ? C16 N2B C5 128.14(12) . . ? C16 N2B H2 118.3(9) . . ? C5 N2B H2 113.5(9) . . ? N1B C12 C13 123.13(13) . . ? N1B C12 H12 118.4 . . ? C13 C12 H12 118.4 . . ? C12 C13 C19 117.65(13) . . ? C12 C13 H13 121.2 . . ? C19 C13 H13 121.2 . . ? C19 C15 C5 118.64(13) . . ? C19 C15 H15 120.7 . . ? C5 C15 H15 120.7 . . ? O1B C16 N2B 124.02(12) . . ? O1B C16 C17 122.40(13) . . ? N2B C16 C17 113.58(12) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C19 C13 120.19(13) . . ? C15 C19 H19 119.9 . . ? C13 C19 H19 119.9 . . ? 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 C18 C9 C10 C11 -0.5(2) . . . . ? C18 C9 C10 C6 -179.91(13) . . . . ? O2A C6 C10 C9 10.6(2) . . . . ? O1A C6 C10 C9 -169.19(12) . . . . ? O2A C6 C10 C11 -168.75(13) . . . . ? O1A C6 C10 C11 11.42(18) . . . . ? C9 C10 C11 C14 0.0(2) . . . . ? C6 C10 C11 C14 179.34(12) . . . . ? C10 C11 C14 C8 0.8(2) . . . . ? C18 C8 C14 C11 -1.1(2) . . . . ? C14 C8 C18 C9 0.5(2) . . . . ? C10 C9 C18 C8 0.3(2) . . . . ? C12 N1B C5 C15 -0.6(2) . . . . ? C12 N1B C5 N2B 178.87(12) . . . . ? N1B C5 N2B C16 172.73(12) . . . . ? C15 C5 N2B C16 -7.8(2) . . . . ? C5 N1B C12 C13 0.4(2) . . . . ? N1B C12 C13 C19 0.1(2) . . . . ? N1B C5 C15 C19 0.2(2) . . . . ? N2B C5 C15 C19 -179.20(13) . . . . ? C5 N2B C16 O1B -0.5(2) . . . . ? C5 N2B C16 C17 179.67(13) . . . . ? C5 C15 C19 C13 0.4(2) . . . . ? C12 C13 C19 C15 -0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 27.84 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.250 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 963008' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(III)-CCDC963009 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminobenzoic acid + 2-acetamido-6-methylpyridine ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C7 H7 N O2, C8 H10 N2 O' _chemical_formula_sum 'C15 H17 N3 O3' _chemical_formula_weight 287.32 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/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 8.4349(17) _cell_length_b 23.547(5) _cell_length_c 7.1270(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.22(3) _cell_angle_gamma 90.00 _cell_volume 1415.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7340 _cell_measurement_theta_min 3.46 _cell_measurement_theta_max 27.87 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9820 _exptl_absorpt_correction_T_max 0.9848 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7340 _diffrn_reflns_av_R_equivalents 0.0746 _diffrn_reflns_av_sigmaI/netI 0.1493 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3315 _reflns_number_gt 1563 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0671P)^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 0 _refine_ls_number_reflns 3315 _refine_ls_number_parameters 208 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1665 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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 O1A O 0.2674(2) 0.60219(7) 0.6071(3) 0.0325(5) Uani 1 1 d . . . N1B N 0.0241(2) 0.66971(8) 0.5140(3) 0.0231(5) Uani 1 1 d . . . O2A O 0.4004(2) 0.67745(7) 0.7174(3) 0.0315(5) Uani 1 1 d . . . C6B C -0.2434(3) 0.66796(11) 0.4061(4) 0.0310(7) Uani 1 1 d . . . H6B H -0.3473 0.6440 0.3663 0.037 Uiso 1 1 calc R . . O1B O 0.1138(2) 0.84614(7) 0.5374(3) 0.0358(5) Uani 1 1 d . . . C3B C 0.0189(3) 0.72644(10) 0.5142(3) 0.0230(6) Uani 1 1 d . . . C7A C 0.7326(3) 0.50795(10) 0.9062(4) 0.0252(6) Uani 1 1 d . . . C4B C -0.1133(3) 0.75768(10) 0.4582(4) 0.0288(6) Uani 1 1 d . . . H4B H -0.1127 0.8035 0.4570 0.035 Uiso 1 1 calc R . . N1A N 0.8414(3) 0.47027(9) 0.9778(3) 0.0334(6) Uani 1 1 d D . . N2B N 0.1606(3) 0.75117(8) 0.5793(3) 0.0253(5) Uani 1 1 d . . . C4A C 0.5086(3) 0.58530(9) 0.7613(3) 0.0230(6) Uani 1 1 d . . . C8A C 0.6085(3) 0.48927(10) 0.7910(4) 0.0277(6) Uani 1 1 d . . . H8A H 0.5998 0.4448 0.7551 0.033 Uiso 1 1 calc R . . C6A C 0.7464(3) 0.56680(10) 0.9414(4) 0.0282(7) Uani 1 1 d . . . H6A H 0.8440 0.5826 1.0250 0.034 Uiso 1 1 calc R . . C9B C 0.1999(3) 0.80736(10) 0.5911(4) 0.0266(6) Uani 1 1 d . . . C9A C 0.4965(3) 0.52707(10) 0.7226(4) 0.0270(6) Uani 1 1 d . . . H9A H 0.3989 0.5115 0.6386 0.032 Uiso 1 1 calc R . . C5A C 0.6362(3) 0.60407(10) 0.8699(4) 0.0260(6) Uani 1 1 d . . . H5A H 0.6487 0.6489 0.8985 0.031 Uiso 1 1 calc R . . C7B C -0.1062(3) 0.64024(10) 0.4597(4) 0.0286(6) Uani 1 1 d . . . C3A C 0.3899(3) 0.62572(11) 0.6939(4) 0.0257(6) Uani 1 1 d . . . C8B C -0.0925(3) 0.57720(10) 0.4614(4) 0.0361(7) Uani 1 1 d . . . H8B H -0.0057 0.5641 0.3592 0.054 Uiso 1 1 calc R . . H9B H -0.2060 0.5586 0.4269 0.054 Uiso 1 1 calc R . . H10B H -0.0558 0.5632 0.5992 0.054 Uiso 1 1 calc R . . C5B C -0.2466(3) 0.72654(11) 0.4037(4) 0.0320(7) Uani 1 1 d . . . H5B H -0.3528 0.7484 0.3594 0.038 Uiso 1 1 calc R . . C11B C 0.3600(3) 0.81752(10) 0.6779(4) 0.0300(7) Uani 1 1 d . . . H12B H 0.4090 0.8566 0.6238 0.045 Uiso 1 1 calc R . . H11B H 0.4379 0.7826 0.6440 0.045 Uiso 1 1 calc R . . H13B H 0.3481 0.8207 0.8284 0.045 Uiso 1 1 calc R . . H1A H 0.183(4) 0.6321(15) 0.580(5) 0.083(11) Uiso 1 1 d . . . H11A H 0.825(4) 0.4262(8) 0.956(4) 0.066(9) Uiso 1 1 d D . . H10A H 0.911(3) 0.4857(11) 1.081(3) 0.063(10) Uiso 1 1 d D . . H2B H 0.243(4) 0.7215(12) 0.621(4) 0.059(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 O1A 0.0318(11) 0.0242(10) 0.0413(12) -0.0035(8) -0.0108(9) 0.0036(8) N1B 0.0235(12) 0.0238(11) 0.0220(12) -0.0008(9) -0.0003(10) -0.0020(9) O2A 0.0315(11) 0.0221(10) 0.0406(12) -0.0002(8) -0.0068(9) 0.0029(8) C6B 0.0249(16) 0.0364(17) 0.0316(17) 0.0019(13) -0.0026(13) -0.0024(12) O1B 0.0330(11) 0.0263(10) 0.0481(13) 0.0037(9) -0.0061(9) 0.0039(8) C3B 0.0232(15) 0.0262(14) 0.0194(15) -0.0019(11) 0.0000(12) -0.0002(11) C7A 0.0244(15) 0.0245(14) 0.0267(15) 0.0000(11) 0.0052(12) 0.0022(11) C4B 0.0271(15) 0.0334(15) 0.0258(16) 0.0009(12) -0.0006(12) 0.0045(12) N1A 0.0266(13) 0.0259(13) 0.0476(17) 0.0026(11) -0.0064(12) 0.0045(10) N2B 0.0247(12) 0.0251(12) 0.0262(13) -0.0023(9) -0.0034(10) -0.0015(10) C4A 0.0222(14) 0.0222(13) 0.0246(15) 0.0023(11) -0.0006(12) 0.0017(11) C8A 0.0292(16) 0.0203(14) 0.0335(17) 0.0023(11) 0.0000(13) 0.0003(11) C6A 0.0247(15) 0.0269(14) 0.0330(18) -0.0033(12) 0.0003(13) -0.0004(11) C9B 0.0323(16) 0.0239(14) 0.0235(15) -0.0018(12) 0.0023(12) -0.0011(12) C9A 0.0279(15) 0.0276(14) 0.0255(16) -0.0009(11) 0.0024(12) 0.0000(12) C5A 0.0268(15) 0.0180(13) 0.0334(17) -0.0017(11) -0.0004(13) 0.0037(11) C7B 0.0299(16) 0.0316(14) 0.0243(16) 0.0002(12) 0.0043(12) -0.0051(12) C3A 0.0251(15) 0.0292(15) 0.0229(16) -0.0022(12) 0.0008(12) -0.0003(12) C8B 0.0338(17) 0.0309(15) 0.0434(19) -0.0013(13) -0.0021(14) -0.0063(13) C5B 0.0267(16) 0.0411(17) 0.0283(17) -0.0004(13) -0.0029(13) 0.0009(12) C11B 0.0304(16) 0.0263(14) 0.0333(17) -0.0020(12) -0.0048(13) -0.0028(11) _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 O1A C3A 1.323(3) . ? O1A H1A 1.02(4) . ? N1B C3B 1.336(3) . ? N1B C7B 1.355(3) . ? O2A C3A 1.233(3) . ? C6B C5B 1.380(3) . ? C6B C7B 1.381(4) . ? C6B H6B 1.0800 . ? O1B C9B 1.227(3) . ? C3B C4B 1.393(3) . ? C3B N2B 1.407(3) . ? C7A N1A 1.374(3) . ? C7A C8A 1.399(4) . ? C7A C6A 1.413(3) . ? C4B C5B 1.396(4) . ? C4B H4B 1.0800 . ? N1A H11A 1.057(17) . ? N1A H10A 1.004(17) . ? N2B C9B 1.367(3) . ? N2B H2B 1.03(3) . ? C4A C5A 1.395(3) . ? C4A C9A 1.402(3) . ? C4A C3A 1.462(3) . ? C8A C9A 1.385(3) . ? C8A H8A 1.0800 . ? C6A C5A 1.375(3) . ? C6A H6A 1.0800 . ? C9B C11B 1.502(4) . ? C9A H9A 1.0800 . ? C5A H5A 1.0800 . ? C7B C8B 1.489(3) . ? C8B H8B 1.0800 . ? C8B H9B 1.0800 . ? C8B H10B 1.0800 . ? C5B H5B 1.0800 . ? C11B H12B 1.0800 . ? C11B H11B 1.0800 . ? C11B H13B 1.0800 . ? 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 C3A O1A H1A 110.1(19) . . ? C3B N1B C7B 119.1(2) . . ? C5B C6B C7B 119.5(2) . . ? C5B C6B H6B 120.3 . . ? C7B C6B H6B 120.3 . . ? N1B C3B C4B 123.6(2) . . ? N1B C3B N2B 112.7(2) . . ? C4B C3B N2B 123.6(2) . . ? N1A C7A C8A 120.8(2) . . ? N1A C7A C6A 120.8(2) . . ? C8A C7A C6A 118.3(2) . . ? C3B C4B C5B 116.4(2) . . ? C3B C4B H4B 121.8 . . ? C5B C4B H4B 121.8 . . ? C7A N1A H11A 119.7(17) . . ? C7A N1A H10A 115.0(17) . . ? H11A N1A H10A 122(2) . . ? C9B N2B C3B 128.8(2) . . ? C9B N2B H2B 118.4(16) . . ? C3B N2B H2B 112.7(16) . . ? C5A C4A C9A 118.3(2) . . ? C5A C4A C3A 120.2(2) . . ? C9A C4A C3A 121.5(2) . . ? C9A C8A C7A 120.8(2) . . ? C9A C8A H8A 119.6 . . ? C7A C8A H8A 119.6 . . ? C5A C6A C7A 120.3(2) . . ? C5A C6A H6A 119.8 . . ? C7A C6A H6A 119.8 . . ? O1B C9B N2B 123.9(2) . . ? O1B C9B C11B 122.7(2) . . ? N2B C9B C11B 113.4(2) . . ? C8A C9A C4A 120.7(2) . . ? C8A C9A H9A 119.7 . . ? C4A C9A H9A 119.7 . . ? C6A C5A C4A 121.5(2) . . ? C6A C5A H5A 119.3 . . ? C4A C5A H5A 119.3 . . ? N1B C7B C6B 121.0(2) . . ? N1B C7B C8B 116.5(2) . . ? C6B C7B C8B 122.6(2) . . ? O2A C3A O1A 122.2(2) . . ? O2A C3A C4A 123.4(2) . . ? O1A C3A C4A 114.4(2) . . ? C7B C8B H8B 109.5 . . ? C7B C8B H9B 109.5 . . ? H8B C8B H9B 109.5 . . ? C7B C8B H10B 109.5 . . ? H8B C8B H10B 109.5 . . ? H9B C8B H10B 109.5 . . ? C6B C5B C4B 120.4(2) . . ? C6B C5B H5B 119.8 . . ? C4B C5B H5B 119.8 . . ? C9B C11B H12B 109.5 . . ? C9B C11B H11B 109.5 . . ? H12B C11B H11B 109.5 . . ? C9B C11B H13B 109.5 . . ? H12B C11B H13B 109.5 . . ? H11B C11B H13B 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7B N1B C3B C4B -1.2(4) . . . . ? C7B N1B C3B N2B 178.1(2) . . . . ? N1B C3B C4B C5B 1.5(4) . . . . ? N2B C3B C4B C5B -177.7(2) . . . . ? N1B C3B N2B C9B 176.9(2) . . . . ? C4B C3B N2B C9B -3.8(4) . . . . ? N1A C7A C8A C9A 178.4(2) . . . . ? C6A C7A C8A C9A -3.8(4) . . . . ? N1A C7A C6A C5A -179.6(2) . . . . ? C8A C7A C6A C5A 2.6(4) . . . . ? C3B N2B C9B O1B -2.7(4) . . . . ? C3B N2B C9B C11B 177.0(2) . . . . ? C7A C8A C9A C4A 2.5(4) . . . . ? C5A C4A C9A C8A 0.1(4) . . . . ? C3A C4A C9A C8A -178.6(2) . . . . ? C7A C6A C5A C4A -0.1(4) . . . . ? C9A C4A C5A C6A -1.3(4) . . . . ? C3A C4A C5A C6A 177.4(2) . . . . ? C3B N1B C7B C6B -0.3(4) . . . . ? C3B N1B C7B C8B 179.6(2) . . . . ? C5B C6B C7B N1B 1.5(4) . . . . ? C5B C6B C7B C8B -178.5(2) . . . . ? C5A C4A C3A O2A 4.8(4) . . . . ? C9A C4A C3A O2A -176.4(2) . . . . ? C5A C4A C3A O1A -174.1(2) . . . . ? C9A C4A C3A O1A 4.6(3) . . . . ? C7B C6B C5B C4B -1.1(4) . . . . ? C3B C4B C5B C6B -0.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.246 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 963009' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(IV)-CCDC963010 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2(4-methoxybenzoic acid) + 4,4-bipyridine ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety '2(C8 H8 O3),C10 H8 N2' _chemical_formula_sum 'C26 H24 N2 O6' _chemical_formula_weight 460.47 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/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 9.0318(7) _cell_length_b 10.8602(9) _cell_length_c 23.5610(19) _cell_angle_alpha 90.00 _cell_angle_beta 97.950(2) _cell_angle_gamma 90.00 _cell_volume 2288.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 31250 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 28.34 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Bruker Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 31250 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 28.34 _reflns_number_total 5695 _reflns_number_gt 4225 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0552P)^2^+0.4859P] 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 none _refine_ls_number_reflns 5695 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 O1A1 O -0.52529(11) 0.31626(10) 0.29886(5) 0.0416(3) Uani 1 1 d . . . O1A2 O 0.77306(11) 0.15678(9) 0.52420(5) 0.0403(3) Uani 1 1 d . . . O2A2 O 0.80584(10) 0.35738(9) 0.54309(4) 0.0360(2) Uani 1 1 d . . . O3A1 O -1.18902(10) 0.45991(9) 0.21591(4) 0.0379(2) Uani 1 1 d . . . O2A1 O -0.53013(11) 0.47566(10) 0.35840(5) 0.0417(3) Uani 1 1 d . . . N1B N -0.24762(12) 0.28500(11) 0.34865(5) 0.0349(3) Uani 1 1 d . . . C7 C 0.05040(13) 0.25991(11) 0.39825(5) 0.0261(3) Uani 1 1 d . . . N2B N 0.50277(12) 0.20832(11) 0.47593(5) 0.0357(3) Uani 1 1 d . . . O3A2 O 1.45603(10) 0.13325(9) 0.62085(5) 0.0405(3) Uani 1 1 d . . . C10 C 0.20835(13) 0.24372(12) 0.42489(5) 0.0261(3) Uani 1 1 d . . . C11 C -0.74806(13) 0.42982(12) 0.29223(5) 0.0269(3) Uani 1 1 d . . . C12 C -0.04737(14) 0.33672(12) 0.42225(6) 0.0296(3) Uani 1 1 d . . . H12 H -0.0137 0.3825 0.4559 0.036 Uiso 1 1 calc R . . C13 C -0.84378(14) 0.50662(12) 0.31709(6) 0.0291(3) Uani 1 1 d . . . H13 H -0.8073 0.5505 0.3511 0.035 Uiso 1 1 calc R . . C14 C -1.04515(13) 0.45558(12) 0.24333(5) 0.0284(3) Uani 1 1 d . . . C15 C -0.94929(15) 0.38075(13) 0.21732(6) 0.0327(3) Uani 1 1 d . . . H15 H -0.9851 0.3380 0.1830 0.039 Uiso 1 1 calc R . . C16 C 1.26147(14) 0.28962(12) 0.60384(6) 0.0296(3) Uani 1 1 d . . . H16 H 1.3277 0.3542 0.6177 0.036 Uiso 1 1 calc R . . C17 C -0.99289(14) 0.52036(12) 0.29290(6) 0.0291(3) Uani 1 1 d . . . H17 H -1.0577 0.5733 0.3101 0.035 Uiso 1 1 calc R . . C18 C 1.31218(14) 0.16845(13) 0.60271(6) 0.0303(3) Uani 1 1 d . . . C19 C 1.01350(13) 0.22096(12) 0.56396(5) 0.0262(3) Uani 1 1 d . . . C20 C -0.00517(14) 0.19713(13) 0.34851(6) 0.0331(3) Uani 1 1 d . . . H20 H 0.0580 0.1441 0.3306 0.040 Uiso 1 1 calc R . . C21 C 1.11205(14) 0.31401(12) 0.58430(5) 0.0282(3) Uani 1 1 d . . . H21 H 1.0766 0.3963 0.5849 0.034 Uiso 1 1 calc R . . C22 C 0.28875(14) 0.33849(12) 0.45457(6) 0.0309(3) Uani 1 1 d . . . H22 H 0.2442 0.4169 0.4579 0.037 Uiso 1 1 calc R . . C23 C -0.80211(14) 0.36868(12) 0.24149(6) 0.0305(3) Uani 1 1 d . . . H23 H -0.7367 0.3181 0.2234 0.037 Uiso 1 1 calc R . . C24 C 1.06675(14) 0.10023(12) 0.56320(6) 0.0302(3) Uani 1 1 d . . . H24 H 1.0006 0.0356 0.5493 0.036 Uiso 1 1 calc R . . C25 C -0.19419(14) 0.34576(13) 0.39651(6) 0.0329(3) Uani 1 1 d . . . H25 H -0.2602 0.3976 0.4136 0.039 Uiso 1 1 calc R . . C26 C 1.21453(15) 0.07430(13) 0.58247(6) 0.0331(3) Uani 1 1 d . . . H26 H 1.2498 -0.0081 0.5819 0.040 Uiso 1 1 calc R . . C27 C -0.59110(14) 0.41124(12) 0.32001(6) 0.0298(3) Uani 1 1 d . . . C28 C 0.85445(14) 0.25254(12) 0.54313(5) 0.0288(3) Uani 1 1 d . . . C29 C 0.28008(14) 0.13119(13) 0.42097(6) 0.0334(3) Uani 1 1 d . . . H29 H 0.2294 0.0646 0.4006 0.040 Uiso 1 1 calc R . . C30 C -1.29573(16) 0.53338(15) 0.23996(8) 0.0448(4) Uani 1 1 d . . . H30A H -1.2983 0.5085 0.2798 0.067 Uiso 1 1 calc R . . H30B H -1.3948 0.5217 0.2178 0.067 Uiso 1 1 calc R . . H30C H -1.2673 0.6203 0.2388 0.067 Uiso 1 1 calc R . . C31 C -0.15326(15) 0.21238(13) 0.32519(6) 0.0377(3) Uani 1 1 d . . . H31 H -0.1894 0.1693 0.2910 0.045 Uiso 1 1 calc R . . C32 C 0.43446(14) 0.31675(13) 0.47907(6) 0.0348(3) Uani 1 1 d . . . H32 H 0.4887 0.3821 0.4991 0.042 Uiso 1 1 calc R . . C33 C 0.42593(15) 0.11756(13) 0.44703(7) 0.0366(3) Uani 1 1 d . . . H33 H 0.4737 0.0403 0.4443 0.044 Uiso 1 1 calc R . . C1 C 1.56100(16) 0.22768(15) 0.64157(8) 0.0444(4) Uani 1 1 d . . . H1A H 1.5642 0.2901 0.6117 0.067 Uiso 1 1 calc R . . H1B H 1.6605 0.1913 0.6515 0.067 Uiso 1 1 calc R . . H1C H 1.5300 0.2662 0.6757 0.067 Uiso 1 1 calc R . . H1 H -0.426(3) 0.306(2) 0.3194(10) 0.085(7) Uiso 1 1 d . . . H2 H 0.672(3) 0.188(2) 0.5062(10) 0.093(7) 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 O1A1 0.0270(5) 0.0408(6) 0.0542(7) -0.0097(5) -0.0036(4) 0.0061(4) O1A2 0.0272(5) 0.0326(5) 0.0576(7) -0.0030(5) -0.0067(4) 0.0004(4) O2A2 0.0325(5) 0.0325(5) 0.0418(6) -0.0045(4) 0.0015(4) 0.0076(4) O3A1 0.0272(5) 0.0409(6) 0.0426(6) -0.0032(4) -0.0053(4) 0.0036(4) O2A1 0.0310(5) 0.0439(6) 0.0476(6) -0.0093(5) -0.0041(4) -0.0012(4) N1B 0.0250(5) 0.0347(6) 0.0438(7) 0.0022(5) 0.0009(5) 0.0029(5) C7 0.0225(5) 0.0248(6) 0.0310(6) 0.0042(5) 0.0039(5) 0.0015(5) N2B 0.0249(5) 0.0372(7) 0.0437(7) 0.0013(5) -0.0001(5) 0.0014(5) O3A2 0.0266(5) 0.0363(6) 0.0561(7) 0.0006(5) -0.0031(4) 0.0057(4) C10 0.0221(5) 0.0281(6) 0.0282(6) 0.0023(5) 0.0043(5) 0.0020(5) C11 0.0257(6) 0.0262(6) 0.0287(6) 0.0035(5) 0.0030(5) -0.0007(5) C12 0.0288(6) 0.0309(7) 0.0291(6) 0.0019(5) 0.0038(5) 0.0042(5) C13 0.0300(6) 0.0288(7) 0.0279(6) -0.0014(5) 0.0017(5) -0.0017(5) C14 0.0261(6) 0.0272(6) 0.0305(6) 0.0052(5) -0.0008(5) -0.0002(5) C15 0.0359(7) 0.0355(7) 0.0252(6) -0.0026(5) -0.0016(5) 0.0028(6) C16 0.0289(6) 0.0291(7) 0.0297(7) -0.0018(5) 0.0003(5) -0.0010(5) C17 0.0278(6) 0.0283(6) 0.0316(7) -0.0009(5) 0.0057(5) 0.0027(5) C18 0.0259(6) 0.0350(7) 0.0298(6) 0.0008(5) 0.0026(5) 0.0048(5) C19 0.0260(6) 0.0292(6) 0.0231(6) -0.0003(5) 0.0028(5) 0.0026(5) C20 0.0271(6) 0.0316(7) 0.0403(7) -0.0059(6) 0.0034(5) 0.0050(5) C21 0.0304(6) 0.0259(6) 0.0277(6) -0.0012(5) 0.0017(5) 0.0028(5) C22 0.0305(6) 0.0262(7) 0.0353(7) 0.0002(5) 0.0021(5) 0.0033(5) C23 0.0314(6) 0.0317(7) 0.0288(6) -0.0004(5) 0.0053(5) 0.0058(5) C24 0.0296(6) 0.0277(7) 0.0330(7) -0.0038(5) 0.0036(5) -0.0009(5) C25 0.0271(6) 0.0347(7) 0.0377(7) 0.0035(6) 0.0072(5) 0.0074(5) C26 0.0321(6) 0.0275(7) 0.0398(8) -0.0012(6) 0.0049(5) 0.0059(5) C27 0.0250(6) 0.0297(7) 0.0345(7) 0.0028(5) 0.0037(5) -0.0012(5) C28 0.0279(6) 0.0315(7) 0.0270(6) -0.0012(5) 0.0034(5) 0.0017(5) C29 0.0271(6) 0.0279(7) 0.0443(8) -0.0029(6) 0.0014(5) 0.0020(5) C30 0.0284(7) 0.0451(9) 0.0594(10) 0.0001(7) 0.0012(6) 0.0050(6) C31 0.0306(7) 0.0379(8) 0.0424(8) -0.0061(6) -0.0030(6) 0.0022(6) C32 0.0298(6) 0.0327(7) 0.0403(8) -0.0003(6) -0.0008(6) -0.0021(5) C33 0.0266(6) 0.0322(7) 0.0500(9) -0.0013(6) 0.0019(6) 0.0078(5) C1 0.0275(7) 0.0450(9) 0.0571(10) 0.0038(7) -0.0075(6) 0.0003(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 O1A1 C27 1.3220(17) . ? O1A1 H1 0.97(2) . ? O1A2 C28 1.3154(16) . ? O1A2 H2 1.01(2) . ? O2A2 C28 1.2202(16) . ? O3A1 C14 1.3696(14) . ? O3A1 C30 1.4274(18) . ? O2A1 C27 1.2136(16) . ? N1B C31 1.3358(19) . ? N1B C25 1.3377(18) . ? C7 C20 1.3883(18) . ? C7 C12 1.3904(18) . ? C7 C10 1.4874(16) . ? N2B C32 1.3362(18) . ? N2B C33 1.3364(18) . ? O3A2 C18 1.3650(15) . ? O3A2 C1 1.4356(18) . ? C10 C22 1.3910(18) . ? C10 C29 1.3923(18) . ? C11 C13 1.3880(18) . ? C11 C23 1.3953(18) . ? C11 C27 1.4907(16) . ? C12 C25 1.3832(17) . ? C12 H12 0.9500 . ? C13 C17 1.3959(17) . ? C13 H13 0.9500 . ? C14 C17 1.3891(18) . ? C14 C15 1.3901(19) . ? C15 C23 1.3781(18) . ? C15 H15 0.9500 . ? C16 C21 1.3898(17) . ? C16 C18 1.3948(19) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C26 1.3908(19) . ? C19 C21 1.3875(18) . ? C19 C24 1.3975(18) . ? C19 C28 1.4923(17) . ? C20 C31 1.3838(17) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C32 1.3823(17) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C26 1.3782(18) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C29 C33 1.3822(18) . ? C29 H29 0.9500 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? 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 C27 O1A1 H1 109.8(14) . . ? C28 O1A2 H2 107.9(14) . . ? C14 O3A1 C30 118.72(11) . . ? C31 N1B C25 117.62(11) . . ? C20 C7 C12 117.53(11) . . ? C20 C7 C10 120.79(11) . . ? C12 C7 C10 121.68(11) . . ? C32 N2B C33 117.84(11) . . ? C18 O3A2 C1 117.49(11) . . ? C22 C10 C29 117.87(11) . . ? C22 C10 C7 121.88(11) . . ? C29 C10 C7 120.24(11) . . ? C13 C11 C23 118.88(11) . . ? C13 C11 C27 120.40(11) . . ? C23 C11 C27 120.71(12) . . ? C25 C12 C7 119.24(12) . . ? C25 C12 H12 120.4 . . ? C7 C12 H12 120.4 . . ? C11 C13 C17 120.93(12) . . ? C11 C13 H13 119.5 . . ? C17 C13 H13 119.5 . . ? O3A1 C14 C17 124.69(12) . . ? O3A1 C14 C15 114.85(11) . . ? C17 C14 C15 120.45(11) . . ? C23 C15 C14 119.83(12) . . ? C23 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C21 C16 C18 118.68(12) . . ? C21 C16 H16 120.7 . . ? C18 C16 H16 120.7 . . ? C14 C17 C13 119.05(12) . . ? C14 C17 H17 120.5 . . ? C13 C17 H17 120.5 . . ? O3A2 C18 C26 115.62(12) . . ? O3A2 C18 C16 123.99(12) . . ? C26 C18 C16 120.39(11) . . ? C21 C19 C24 118.83(11) . . ? C21 C19 C28 119.24(11) . . ? C24 C19 C28 121.92(11) . . ? C31 C20 C7 119.54(12) . . ? C31 C20 H20 120.2 . . ? C7 C20 H20 120.2 . . ? C19 C21 C16 121.52(12) . . ? C19 C21 H21 119.2 . . ? C16 C21 H21 119.2 . . ? C32 C22 C10 118.96(12) . . ? C32 C22 H22 120.5 . . ? C10 C22 H22 120.5 . . ? C15 C23 C11 120.80(12) . . ? C15 C23 H23 119.6 . . ? C11 C23 H23 119.6 . . ? C26 C24 C19 120.45(12) . . ? C26 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? N1B C25 C12 123.14(13) . . ? N1B C25 H25 118.4 . . ? C12 C25 H25 118.4 . . ? C24 C26 C18 120.13(12) . . ? C24 C26 H26 119.9 . . ? C18 C26 H26 119.9 . . ? O2A1 C27 O1A1 123.33(12) . . ? O2A1 C27 C11 123.72(12) . . ? O1A1 C27 C11 112.95(11) . . ? O2A2 C28 O1A2 123.60(11) . . ? O2A2 C28 C19 123.00(12) . . ? O1A2 C28 C19 113.40(11) . . ? C33 C29 C10 119.21(12) . . ? C33 C29 H29 120.4 . . ? C10 C29 H29 120.4 . . ? O3A1 C30 H30A 109.5 . . ? O3A1 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O3A1 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N1B C31 C20 122.91(13) . . ? N1B C31 H31 118.5 . . ? C20 C31 H31 118.5 . . ? N2B C32 C22 123.21(12) . . ? N2B C32 H32 118.4 . . ? C22 C32 H32 118.4 . . ? N2B C33 C29 122.90(13) . . ? N2B C33 H33 118.5 . . ? C29 C33 H33 118.5 . . ? O3A2 C1 H1A 109.5 . . ? O3A2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O3A2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C20 C7 C10 C22 148.19(14) . . . . ? C12 C7 C10 C22 -32.56(19) . . . . ? C20 C7 C10 C29 -32.25(19) . . . . ? C12 C7 C10 C29 147.00(13) . . . . ? C20 C7 C12 C25 1.00(19) . . . . ? C10 C7 C12 C25 -178.27(12) . . . . ? C23 C11 C13 C17 1.75(19) . . . . ? C27 C11 C13 C17 -177.03(12) . . . . ? C30 O3A1 C14 C17 -1.6(2) . . . . ? C30 O3A1 C14 C15 179.28(13) . . . . ? O3A1 C14 C15 C23 -179.46(12) . . . . ? C17 C14 C15 C23 1.3(2) . . . . ? O3A1 C14 C17 C13 179.15(12) . . . . ? C15 C14 C17 C13 -1.7(2) . . . . ? C11 C13 C17 C14 0.2(2) . . . . ? C1 O3A2 C18 C26 179.40(13) . . . . ? C1 O3A2 C18 C16 -0.8(2) . . . . ? C21 C16 C18 O3A2 -179.86(12) . . . . ? C21 C16 C18 C26 -0.1(2) . . . . ? C12 C7 C20 C31 -0.3(2) . . . . ? C10 C7 C20 C31 178.93(13) . . . . ? C24 C19 C21 C16 -0.08(19) . . . . ? C28 C19 C21 C16 -179.59(12) . . . . ? C18 C16 C21 C19 0.07(19) . . . . ? C29 C10 C22 C32 -0.6(2) . . . . ? C7 C10 C22 C32 179.01(12) . . . . ? C14 C15 C23 C11 0.6(2) . . . . ? C13 C11 C23 C15 -2.2(2) . . . . ? C27 C11 C23 C15 176.62(13) . . . . ? C21 C19 C24 C26 0.1(2) . . . . ? C28 C19 C24 C26 179.64(12) . . . . ? C31 N1B C25 C12 0.1(2) . . . . ? C7 C12 C25 N1B -0.9(2) . . . . ? C19 C24 C26 C18 -0.2(2) . . . . ? O3A2 C18 C26 C24 179.94(13) . . . . ? C16 C18 C26 C24 0.2(2) . . . . ? C13 C11 C27 O2A1 -13.7(2) . . . . ? C23 C11 C27 O2A1 167.53(14) . . . . ? C13 C11 C27 O1A1 165.65(12) . . . . ? C23 C11 C27 O1A1 -13.10(18) . . . . ? C21 C19 C28 O2A2 -0.1(2) . . . . ? C24 C19 C28 O2A2 -179.56(13) . . . . ? C21 C19 C28 O1A2 179.05(12) . . . . ? C24 C19 C28 O1A2 -0.44(18) . . . . ? C22 C10 C29 C33 0.9(2) . . . . ? C7 C10 C29 C33 -178.73(13) . . . . ? C25 N1B C31 C20 0.6(2) . . . . ? C7 C20 C31 N1B -0.5(2) . . . . ? C33 N2B C32 C22 0.8(2) . . . . ? C10 C22 C32 N2B -0.3(2) . . . . ? C32 N2B C33 C29 -0.5(2) . . . . ? C10 C29 C33 N2B -0.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.249 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 963010' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(V)-CCDC963011 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminobenzoic acid + 6-aminoquinoline ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C7 H6 N O2, C9 H9 N2' _chemical_formula_sum 'C16 H15 N3 O2' _chemical_formula_weight 281.31 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/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 7.3345(15) _cell_length_b 9.1868(18) _cell_length_c 21.307(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.30(3) _cell_angle_gamma 90.00 _cell_volume 1433.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6289 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.49 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9860 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Bruker Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6289 _diffrn_reflns_av_R_equivalents 0.0143 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3266 _reflns_number_gt 2867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0566P)^2^+0.3315P] 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 0 _refine_ls_number_reflns 3266 _refine_ls_number_parameters 210 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.067 _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 O2A O 0.40356(10) 0.54953(9) 0.10204(3) 0.02590(19) Uani 1 1 d . . . O1A O 0.11519(10) 0.61120(9) 0.11604(4) 0.02740(19) Uani 1 1 d . . . N1B N 0.15477(12) 0.74707(9) 0.01159(4) 0.0232(2) Uani 1 1 d . . . C4 C 0.31018(14) 1.09666(11) -0.05118(5) 0.0224(2) Uani 1 1 d . . . H4 H 0.3437 1.1372 -0.0899 0.027 Uiso 1 1 calc R . . C5 C 0.21286(14) 0.97743(12) 0.06343(5) 0.0238(2) Uani 1 1 d . . . H5 H 0.1803 0.9376 0.1024 0.029 Uiso 1 1 calc R . . C6 C 0.26076(13) 0.44283(11) 0.18768(5) 0.0205(2) Uani 1 1 d . . . N1A N 0.25408(13) 0.13996(10) 0.33488(4) 0.0240(2) Uani 1 1 d . . . H3 H 0.152(2) 0.1355(15) 0.3564(6) 0.034(4) Uiso 1 1 d . . . C8 C 0.25194(13) 0.95097(11) -0.04924(5) 0.0204(2) Uani 1 1 d . . . N2B N 0.37378(15) 1.32473(10) 0.00082(5) 0.0310(2) Uani 1 1 d D . . H2 H 0.443(2) 1.3555(17) -0.0340(6) 0.045(4) Uiso 1 1 d D . . H1 H 0.393(2) 1.3735(16) 0.0377(7) 0.035(4) Uiso 1 1 d . . . C10 C 0.26169(14) 0.54126(11) 0.13195(5) 0.0206(2) Uani 1 1 d . . . C11 C 0.10670(14) 0.33077(12) 0.27288(5) 0.0238(2) Uani 1 1 d . . . H11 H 0.0013 0.3233 0.2966 0.029 Uiso 1 1 calc R . . C12 C 0.20539(13) 0.89011(11) 0.00883(5) 0.0201(2) Uani 1 1 d . . . C13 C 0.25832(14) 0.24154(11) 0.28799(5) 0.0206(2) Uani 1 1 d . . . C14 C 0.26695(14) 1.11926(12) 0.06016(5) 0.0242(2) Uani 1 1 d . . . H14 H 0.2698 1.1777 0.0970 0.029 Uiso 1 1 calc R . . C15 C 0.41290(14) 0.35593(12) 0.20369(5) 0.0259(2) Uani 1 1 d . . . H15 H 0.5186 0.3646 0.1802 0.031 Uiso 1 1 calc R . . C16 C 0.10895(14) 0.42950(11) 0.22389(5) 0.0230(2) Uani 1 1 d . . . H16 H 0.0052 0.4894 0.2147 0.028 Uiso 1 1 calc R . . C17 C 0.23675(15) 0.86044(12) -0.10313(5) 0.0256(2) Uani 1 1 d . . . H17 H 0.2652 0.8982 -0.1429 0.031 Uiso 1 1 calc R . . C18 C 0.41329(14) 0.25773(12) 0.25280(5) 0.0267(2) Uani 1 1 d . . . H18 H 0.5191 0.2008 0.2628 0.032 Uiso 1 1 calc R . . C19 C 0.14348(15) 0.66381(12) -0.03908(5) 0.0273(2) Uani 1 1 d . . . H19 H 0.1090 0.5647 -0.0353 0.033 Uiso 1 1 calc R . . C20 C 0.31943(14) 1.18171(11) 0.00245(5) 0.0226(2) Uani 1 1 d . . . C21 C 0.18116(16) 0.71848(12) -0.09811(5) 0.0283(2) Uani 1 1 d . . . H21 H 0.1685 0.6582 -0.1343 0.034 Uiso 1 1 calc R . . H6 H 0.3615(19) 0.1037(15) 0.3514(6) 0.030(3) Uiso 1 1 d . . . H7 H 0.136(2) 0.697(2) 0.0558(8) 0.063(5) 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 O2A 0.0235(4) 0.0313(4) 0.0232(4) 0.0029(3) 0.0043(3) -0.0034(3) O1A 0.0268(4) 0.0273(4) 0.0287(4) 0.0087(3) 0.0059(3) 0.0038(3) N1B 0.0221(4) 0.0199(4) 0.0276(4) 0.0045(3) 0.0025(3) 0.0001(3) C4 0.0254(5) 0.0205(5) 0.0215(5) 0.0039(4) 0.0028(4) 0.0008(4) C5 0.0234(5) 0.0277(5) 0.0205(5) 0.0034(4) 0.0032(4) -0.0005(4) C6 0.0225(5) 0.0187(5) 0.0205(5) -0.0011(4) 0.0012(4) -0.0024(4) N1A 0.0224(5) 0.0248(5) 0.0247(4) 0.0055(4) 0.0009(4) -0.0004(4) C8 0.0189(5) 0.0200(5) 0.0222(5) 0.0019(4) 0.0006(4) 0.0025(4) N2B 0.0408(6) 0.0213(5) 0.0313(5) -0.0031(4) 0.0064(4) -0.0072(4) C10 0.0239(5) 0.0178(5) 0.0201(5) -0.0029(4) 0.0017(4) -0.0038(4) C11 0.0221(5) 0.0262(5) 0.0236(5) 0.0022(4) 0.0051(4) 0.0007(4) C12 0.0172(5) 0.0195(5) 0.0235(5) 0.0036(4) 0.0003(4) 0.0012(4) C13 0.0229(5) 0.0187(5) 0.0199(5) -0.0008(4) -0.0010(4) -0.0031(4) C14 0.0238(5) 0.0270(5) 0.0220(5) -0.0038(4) 0.0018(4) -0.0003(4) C15 0.0215(5) 0.0282(5) 0.0287(5) 0.0040(4) 0.0069(4) 0.0001(4) C16 0.0222(5) 0.0237(5) 0.0231(5) 0.0015(4) 0.0014(4) 0.0032(4) C17 0.0289(5) 0.0255(5) 0.0224(5) 0.0008(4) 0.0025(4) 0.0019(4) C18 0.0213(5) 0.0274(5) 0.0317(6) 0.0057(4) 0.0028(4) 0.0043(4) C19 0.0270(5) 0.0192(5) 0.0358(6) 0.0001(4) 0.0030(4) -0.0015(4) C20 0.0209(5) 0.0195(5) 0.0275(5) 0.0008(4) 0.0016(4) 0.0007(4) C21 0.0308(6) 0.0248(5) 0.0292(5) -0.0057(4) 0.0013(4) 0.0004(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 O2A C10 1.2534(13) . ? O1A C10 1.2808(13) . ? N1B C19 1.3218(15) . ? N1B C12 1.3678(13) . ? N1B H7 1.065(18) . ? C4 C20 1.3827(15) . ? C4 C8 1.4063(14) . ? C4 H4 0.9500 . ? C5 C14 1.3650(16) . ? C5 C12 1.4116(14) . ? C5 H5 0.9500 . ? C6 C16 1.3960(15) . ? C6 C15 1.3982(15) . ? C6 C10 1.4929(14) . ? N1A C13 1.3687(13) . ? N1A H3 0.902(15) . ? N1A H6 0.908(14) . ? C8 C17 1.4170(14) . ? C8 C12 1.4172(14) . ? N2B C20 1.3741(14) . ? N2B H2 0.966(13) . ? N2B H1 0.908(15) . ? C11 C16 1.3836(14) . ? C11 C13 1.4040(15) . ? C11 H11 0.9500 . ? C13 C18 1.4051(15) . ? C14 C20 1.4296(15) . ? C14 H14 0.9500 . ? C15 C18 1.3815(15) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C21 1.3724(16) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C21 1.3967(16) . ? C19 H19 0.9500 . ? C21 H21 0.9500 . ? 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 C19 N1B C12 121.69(9) . . ? C19 N1B H7 117.8(10) . . ? C12 N1B H7 120.2(10) . . ? C20 C4 C8 120.93(9) . . ? C20 C4 H4 119.5 . . ? C8 C4 H4 119.5 . . ? C14 C5 C12 119.86(9) . . ? C14 C5 H5 120.1 . . ? C12 C5 H5 120.1 . . ? C16 C6 C15 117.76(9) . . ? C16 C6 C10 122.21(9) . . ? C15 C6 C10 119.99(9) . . ? C13 N1A H3 117.2(9) . . ? C13 N1A H6 118.5(9) . . ? H3 N1A H6 120.9(12) . . ? C4 C8 C17 123.00(9) . . ? C4 C8 C12 119.34(9) . . ? C17 C8 C12 117.66(9) . . ? C20 N2B H2 117.8(9) . . ? C20 N2B H1 118.8(9) . . ? H2 N2B H1 117.1(13) . . ? O2A C10 O1A 122.91(9) . . ? O2A C10 C6 118.89(9) . . ? O1A C10 C6 118.19(9) . . ? C16 C11 C13 120.80(9) . . ? C16 C11 H11 119.6 . . ? C13 C11 H11 119.6 . . ? N1B C12 C5 120.55(9) . . ? N1B C12 C8 119.75(9) . . ? C5 C12 C8 119.70(9) . . ? N1A C13 C11 120.97(9) . . ? N1A C13 C18 120.98(10) . . ? C11 C13 C18 118.05(9) . . ? C5 C14 C20 121.36(9) . . ? C5 C14 H14 119.3 . . ? C20 C14 H14 119.3 . . ? C18 C15 C6 121.63(10) . . ? C18 C15 H15 119.2 . . ? C6 C15 H15 119.2 . . ? C11 C16 C6 121.26(10) . . ? C11 C16 H16 119.4 . . ? C6 C16 H16 119.4 . . ? C21 C17 C8 120.30(10) . . ? C21 C17 H17 119.8 . . ? C8 C17 H17 119.8 . . ? C15 C18 C13 120.45(10) . . ? C15 C18 H18 119.8 . . ? C13 C18 H18 119.8 . . ? N1B C19 C21 121.40(10) . . ? N1B C19 H19 119.3 . . ? C21 C19 H19 119.3 . . ? N2B C20 C4 121.34(10) . . ? N2B C20 C14 119.88(10) . . ? C4 C20 C14 118.77(9) . . ? C17 C21 C19 119.14(10) . . ? C17 C21 H21 120.4 . . ? C19 C21 H21 120.4 . . ? 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 C20 C4 C8 C17 178.71(10) . . . . ? C20 C4 C8 C12 -1.16(15) . . . . ? C16 C6 C10 O2A 179.01(9) . . . . ? C15 C6 C10 O2A -3.45(14) . . . . ? C16 C6 C10 O1A -2.55(14) . . . . ? C15 C6 C10 O1A 175.00(9) . . . . ? C19 N1B C12 C5 178.74(10) . . . . ? C19 N1B C12 C8 -1.70(15) . . . . ? C14 C5 C12 N1B 178.77(10) . . . . ? C14 C5 C12 C8 -0.80(15) . . . . ? C4 C8 C12 N1B -177.71(9) . . . . ? C17 C8 C12 N1B 2.41(14) . . . . ? C4 C8 C12 C5 1.86(14) . . . . ? C17 C8 C12 C5 -178.02(9) . . . . ? C16 C11 C13 N1A -177.53(9) . . . . ? C16 C11 C13 C18 1.32(15) . . . . ? C12 C5 C14 C20 -0.97(16) . . . . ? C16 C6 C15 C18 1.26(16) . . . . ? C10 C6 C15 C18 -176.39(10) . . . . ? C13 C11 C16 C6 0.53(16) . . . . ? C15 C6 C16 C11 -1.81(15) . . . . ? C10 C6 C16 C11 175.79(9) . . . . ? C4 C8 C17 C21 179.22(10) . . . . ? C12 C8 C17 C21 -0.91(15) . . . . ? C6 C15 C18 C13 0.58(17) . . . . ? N1A C13 C18 C15 176.99(10) . . . . ? C11 C13 C18 C15 -1.86(16) . . . . ? C12 N1B C19 C21 -0.61(16) . . . . ? C8 C4 C20 N2B -179.10(10) . . . . ? C8 C4 C20 C14 -0.57(15) . . . . ? C5 C14 C20 N2B -179.78(10) . . . . ? C5 C14 C20 C4 1.67(16) . . . . ? C8 C17 C21 C19 -1.30(16) . . . . ? N1B C19 C21 C17 2.13(17) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.285 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 963011' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(VI)-CCDC963012 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-nitrobenzoic acid + quinoline ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C7 H5 N O4, C9 H7 N' _chemical_formula_sum 'C16 H12 N2 O4' _chemical_formula_weight 296.28 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 3.7592(13) _cell_length_b 27.082(9) _cell_length_c 6.551(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.735(8) _cell_angle_gamma 90.00 _cell_volume 666.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5055 _cell_measurement_theta_min 1.50 _cell_measurement_theta_max 26.50 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9766 _exptl_absorpt_correction_T_max 0.9808 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Bruker Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5055 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0682 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 26.50 _reflns_number_total 2702 _reflns_number_gt 1894 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0472P)^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 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration unknown _refine_ls_number_reflns 2702 _refine_ls_number_parameters 204 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0837 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 O1A O 1.9830(6) 1.20186(8) 0.1881(3) 0.0363(6) Uani 1 1 d . . . H1 H 2.084(10) 1.1762(15) 0.092(6) 0.067(12) Uiso 1 1 d . . . N1B N 2.2251(6) 1.14060(9) -0.0869(4) 0.0285(6) Uani 1 1 d . . . O3A O 1.2588(8) 1.38328(9) 0.7901(4) 0.0550(8) Uani 1 1 d . . . N4 N 1.3138(7) 1.39259(10) 0.6099(4) 0.0338(7) Uani 1 1 d . . . O4A O 1.2315(7) 1.43171(9) 0.5300(4) 0.0542(7) Uani 1 1 d . . . C6 C 1.7767(7) 1.28341(11) 0.2422(5) 0.0229(6) Uani 1 1 d . . . O2A O 2.0117(7) 1.25516(9) -0.0703(4) 0.0423(6) Uani 1 1 d . . . C8 C 1.6993(8) 1.27320(10) 0.4447(5) 0.0280(7) Uani 1 1 d . . . H8 H 1.7513 1.2415 0.4993 0.034 Uiso 1 1 calc R . . C9 C 2.4401(8) 1.08056(12) -0.4065(5) 0.0298(7) Uani 1 1 d . . . H9 H 2.5171 1.0604 -0.5160 0.036 Uiso 1 1 calc R . . C10 C 2.4739(9) 1.13074(12) -0.4189(5) 0.0333(8) Uani 1 1 d . . . H10 H 2.5714 1.1459 -0.5364 0.040 Uiso 1 1 calc R . . C11 C 2.2923(8) 1.05869(11) -0.2329(5) 0.0263(7) Uani 1 1 d . . . C12 C 1.9996(9) 1.02002(11) 0.1229(5) 0.0345(8) Uani 1 1 d . . . H12 H 1.9022 1.0065 0.2436 0.041 Uiso 1 1 calc R . . C13 C 2.2422(8) 1.00758(12) -0.2111(5) 0.0323(8) Uani 1 1 d . . . H13 H 2.3064 0.9860 -0.3188 0.039 Uiso 1 1 calc R . . C14 C 2.0392(8) 1.07011(11) 0.1056(5) 0.0313(8) Uani 1 1 d . . . H14 H 1.9670 1.0911 0.2135 0.038 Uiso 1 1 calc R . . C15 C 1.9353(8) 1.24535(11) 0.1043(5) 0.0283(8) Uani 1 1 d . . . C16 C 2.1873(7) 1.09056(10) -0.0724(4) 0.0239(7) Uani 1 1 d . . . C17 C 1.5531(8) 1.36576(12) 0.2824(5) 0.0307(7) Uani 1 1 d . . . H17 H 1.5018 1.3976 0.2284 0.037 Uiso 1 1 calc R . . C18 C 1.5472(8) 1.30878(11) 0.5673(5) 0.0309(8) Uani 1 1 d . . . H18 H 1.4926 1.3020 0.7057 0.037 Uiso 1 1 calc R . . C19 C 1.4777(8) 1.35419(10) 0.4826(5) 0.0253(7) Uani 1 1 d . . . C20 C 2.3607(8) 1.15910(13) -0.2537(5) 0.0319(8) Uani 1 1 d . . . H20 H 2.3834 1.1940 -0.2629 0.038 Uiso 1 1 calc R . . C21 C 1.7049(9) 1.32976(11) 0.1639(5) 0.0315(8) Uani 1 1 d . . . H21 H 1.7612 1.3369 0.0260 0.038 Uiso 1 1 calc R . . C22 C 2.1013(9) 0.98863(12) -0.0358(6) 0.0352(8) Uani 1 1 d . . . H22 H 2.0725 0.9539 -0.0219 0.042 Uiso 1 1 calc 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 O1A 0.0542(15) 0.0245(13) 0.0306(13) -0.0002(10) 0.0090(11) 0.0081(10) N1B 0.0315(13) 0.0264(14) 0.0278(16) -0.0005(11) 0.0037(11) 0.0023(11) O3A 0.087(2) 0.0493(18) 0.0297(15) -0.0017(12) 0.0190(14) 0.0164(13) N4 0.0365(16) 0.0326(16) 0.0323(17) -0.0025(14) 0.0010(13) 0.0041(13) O4A 0.084(2) 0.0344(16) 0.0438(15) 0.0005(12) 0.0092(14) 0.0213(13) C6 0.0227(15) 0.0251(16) 0.0209(15) -0.0022(13) 0.0021(12) -0.0010(12) O2A 0.0621(17) 0.0382(14) 0.0269(14) 0.0018(11) 0.0145(12) 0.0095(12) C8 0.0351(18) 0.0258(18) 0.0232(17) 0.0030(13) 0.0038(14) -0.0008(13) C9 0.0267(16) 0.038(2) 0.0244(17) -0.0053(15) 0.0025(13) 0.0034(14) C10 0.0337(18) 0.042(2) 0.0247(18) 0.0028(15) 0.0063(14) -0.0011(14) C11 0.0246(17) 0.0271(18) 0.0273(18) -0.0013(13) 0.0003(14) 0.0031(12) C12 0.0349(18) 0.034(2) 0.035(2) 0.0069(15) 0.0034(15) -0.0002(15) C13 0.0341(18) 0.0292(19) 0.034(2) -0.0057(14) 0.0034(15) -0.0005(14) C14 0.0328(18) 0.031(2) 0.0301(19) -0.0003(14) -0.0005(14) 0.0023(13) C15 0.0297(18) 0.0254(19) 0.030(2) -0.0026(15) 0.0022(15) 0.0037(13) C16 0.0225(14) 0.0251(17) 0.0241(17) -0.0007(12) 0.0007(13) 0.0028(12) C17 0.0381(18) 0.0247(16) 0.0293(19) 0.0036(14) 0.0035(15) 0.0027(14) C18 0.0388(18) 0.0320(19) 0.0220(18) 0.0015(14) 0.0043(14) 0.0011(14) C19 0.0265(15) 0.0218(17) 0.0276(17) -0.0035(13) 0.0047(13) 0.0009(11) C20 0.0341(19) 0.0322(19) 0.0295(18) 0.0006(15) 0.0048(15) 0.0010(14) C21 0.0358(18) 0.033(2) 0.0262(18) 0.0026(15) 0.0028(15) -0.0006(13) C22 0.0360(18) 0.0244(18) 0.045(2) 0.0010(15) 0.0045(16) -0.0023(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 O1A C15 1.311(3) . ? O1A H1 1.02(4) . ? N1B C20 1.311(4) . ? N1B C16 1.366(4) . ? O3A N4 1.227(4) . ? N4 O4A 1.220(3) . ? N4 C19 1.473(4) . ? C6 C21 1.382(4) . ? C6 C8 1.389(4) . ? C6 C15 1.500(4) . ? O2A C15 1.212(4) . ? C8 C18 1.383(4) . ? C8 H8 0.9500 . ? C9 C10 1.368(4) . ? C9 C11 1.403(4) . ? C9 H9 0.9500 . ? C10 C20 1.398(5) . ? C10 H10 0.9500 . ? C11 C13 1.404(4) . ? C11 C16 1.420(4) . ? C12 C14 1.370(4) . ? C12 C22 1.400(4) . ? C12 H12 0.9500 . ? C13 C22 1.371(5) . ? C13 H13 0.9500 . ? C14 C16 1.411(4) . ? C14 H14 0.9500 . ? C17 C21 1.375(4) . ? C17 C19 1.381(4) . ? C17 H17 0.9500 . ? C18 C19 1.373(4) . ? C18 H18 0.9500 . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? 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 C15 O1A H1 114(2) . . ? C20 N1B C16 118.6(3) . . ? O4A N4 O3A 123.1(3) . . ? O4A N4 C19 118.4(3) . . ? O3A N4 C19 118.4(3) . . ? C21 C6 C8 119.6(3) . . ? C21 C6 C15 118.6(3) . . ? C8 C6 C15 121.9(3) . . ? C18 C8 C6 120.6(3) . . ? C18 C8 H8 119.7 . . ? C6 C8 H8 119.7 . . ? C10 C9 C11 120.4(3) . . ? C10 C9 H9 119.8 . . ? C11 C9 H9 119.8 . . ? C9 C10 C20 118.1(3) . . ? C9 C10 H10 121.0 . . ? C20 C10 H10 121.0 . . ? C9 C11 C13 123.6(3) . . ? C9 C11 C16 117.4(3) . . ? C13 C11 C16 119.0(3) . . ? C14 C12 C22 120.6(3) . . ? C14 C12 H12 119.7 . . ? C22 C12 H12 119.7 . . ? C22 C13 C11 120.5(3) . . ? C22 C13 H13 119.7 . . ? C11 C13 H13 119.7 . . ? C12 C14 C16 120.1(3) . . ? C12 C14 H14 120.0 . . ? C16 C14 H14 120.0 . . ? O2A C15 O1A 124.0(3) . . ? O2A C15 C6 121.3(3) . . ? O1A C15 C6 114.7(3) . . ? N1B C16 C14 119.3(3) . . ? N1B C16 C11 121.4(3) . . ? C14 C16 C11 119.3(3) . . ? C21 C17 C19 117.8(3) . . ? C21 C17 H17 121.1 . . ? C19 C17 H17 121.1 . . ? C19 C18 C8 117.9(3) . . ? C19 C18 H18 121.1 . . ? C8 C18 H18 121.1 . . ? C18 C19 C17 123.1(3) . . ? C18 C19 N4 118.8(3) . . ? C17 C19 N4 118.0(3) . . ? N1B C20 C10 124.1(3) . . ? N1B C20 H20 117.9 . . ? C10 C20 H20 117.9 . . ? C17 C21 C6 121.0(3) . . ? C17 C21 H21 119.5 . . ? C6 C21 H21 119.5 . . ? C13 C22 C12 120.5(3) . . ? C13 C22 H22 119.8 . . ? C12 C22 H22 119.8 . . ? 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 C21 C6 C8 C18 0.8(4) . . . . ? C15 C6 C8 C18 -178.9(3) . . . . ? C11 C9 C10 C20 0.6(5) . . . . ? C10 C9 C11 C13 178.6(3) . . . . ? C10 C9 C11 C16 -1.0(5) . . . . ? C9 C11 C13 C22 179.0(3) . . . . ? C16 C11 C13 C22 -1.4(4) . . . . ? C22 C12 C14 C16 -0.7(4) . . . . ? C21 C6 C15 O2A 2.6(5) . . . . ? C8 C6 C15 O2A -177.7(3) . . . . ? C21 C6 C15 O1A -177.6(3) . . . . ? C8 C6 C15 O1A 2.1(4) . . . . ? C20 N1B C16 C14 -179.5(3) . . . . ? C20 N1B C16 C11 0.2(4) . . . . ? C12 C14 C16 N1B -180.0(3) . . . . ? C12 C14 C16 C11 0.3(4) . . . . ? C9 C11 C16 N1B 0.6(4) . . . . ? C13 C11 C16 N1B -179.0(3) . . . . ? C9 C11 C16 C14 -179.6(3) . . . . ? C13 C11 C16 C14 0.7(4) . . . . ? C6 C8 C18 C19 -0.3(4) . . . . ? C8 C18 C19 C17 -0.1(5) . . . . ? C8 C18 C19 N4 179.6(3) . . . . ? C21 C17 C19 C18 0.0(4) . . . . ? C21 C17 C19 N4 -179.8(3) . . . . ? O4A N4 C19 C18 -175.3(3) . . . . ? O3A N4 C19 C18 3.0(4) . . . . ? O4A N4 C19 C17 4.5(4) . . . . ? O3A N4 C19 C17 -177.2(3) . . . . ? C16 N1B C20 C10 -0.7(5) . . . . ? C9 C10 C20 N1B 0.3(5) . . . . ? C19 C17 C21 C6 0.5(5) . . . . ? C8 C6 C21 C17 -0.9(4) . . . . ? C15 C6 C21 C17 178.7(3) . . . . ? C11 C13 C22 C12 1.1(5) . . . . ? C14 C12 C22 C13 0.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.159 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 963012' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(VII)-CCDC963014 _audit_creation_method SHELXL-97 _chemical_name_systematic ; benzoic acid + 2-aminopyridine ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C7 H5 O2, C5 H7 N2' _chemical_formula_sum 'C12 H12 N2 O2' _chemical_formula_weight 216.24 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.500(2) _cell_length_b 15.191(3) _cell_length_c 12.228(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2136.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4451 _cell_measurement_theta_min 3.77 _cell_measurement_theta_max 27.88 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9861 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4451 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 27.88 _reflns_number_total 2433 _reflns_number_gt 1432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0581P)^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 0 _refine_ls_number_reflns 2433 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1054 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _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 O1A O 0.05123(9) 0.56884(7) 0.12465(8) 0.0246(3) Uani 1 1 d . . . O2A O -0.12293(10) 0.62721(7) 0.08896(8) 0.0264(3) Uani 1 1 d . . . N1B N -0.04343(11) 0.49008(9) 0.29643(10) 0.0211(3) Uani 1 1 d . . . C4 C 0.03011(14) 0.65713(9) -0.03503(11) 0.0200(4) Uani 1 1 d . . . N2B N -0.22443(13) 0.55327(9) 0.27654(11) 0.0282(4) Uani 1 1 d . . . C6 C -0.04395(14) 0.70401(10) -0.10415(11) 0.0233(4) Uani 1 1 d . . . H6 H -0.1246 0.7073 -0.0877 0.028 Uiso 1 1 calc R . . C7 C -0.01813(14) 0.61469(10) 0.06636(11) 0.0203(4) Uani 1 1 d . . . C8 C -0.00109(14) 0.74572(10) -0.19642(12) 0.0271(4) Uani 1 1 d . . . H8 H -0.0522 0.7775 -0.2429 0.032 Uiso 1 1 calc R . . C9 C -0.19034(15) 0.44900(10) 0.42283(12) 0.0247(4) Uani 1 1 d . . . H9 H -0.2681 0.4530 0.4485 0.030 Uiso 1 1 calc R . . C10 C 0.03400(15) 0.43706(10) 0.34863(12) 0.0250(4) Uani 1 1 d . . . H10 H 0.1115 0.4332 0.3221 0.030 Uiso 1 1 calc R . . C11 C -0.15407(14) 0.49856(10) 0.33095(11) 0.0223(4) Uani 1 1 d . . . C12 C 0.14737(15) 0.65275(10) -0.06053(12) 0.0250(4) Uani 1 1 d . . . H12 H 0.1987 0.6207 -0.0145 0.030 Uiso 1 1 calc R . . C13 C -0.11228(15) 0.39541(11) 0.47426(13) 0.0276(4) Uani 1 1 d . . . H13 H -0.1365 0.3616 0.5356 0.033 Uiso 1 1 calc R . . C14 C 0.11631(15) 0.74109(11) -0.22092(12) 0.0270(4) Uani 1 1 d . . . H14 H 0.1457 0.7696 -0.2843 0.032 Uiso 1 1 calc R . . C15 C 0.19058(16) 0.69499(10) -0.15312(12) 0.0286(4) Uani 1 1 d . . . H15 H 0.2712 0.6921 -0.1696 0.034 Uiso 1 1 calc R . . C16 C 0.00276(15) 0.38947(11) 0.43808(12) 0.0280(4) Uani 1 1 d . . . H16 H 0.0575 0.3532 0.4749 0.034 Uiso 1 1 calc R . . H5 H -0.1951(18) 0.5828(13) 0.2118(17) 0.055(6) Uiso 1 1 d . . . H7 H -0.2984(18) 0.5631(12) 0.3056(15) 0.046(6) Uiso 1 1 d . . . H1 H -0.0130(17) 0.5223(13) 0.2320(15) 0.051(5) 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 O1A 0.0195(6) 0.0321(7) 0.0221(6) 0.0061(5) -0.0020(5) 0.0016(5) O2A 0.0185(7) 0.0376(7) 0.0233(6) 0.0019(5) 0.0016(5) 0.0005(5) N1B 0.0188(8) 0.0243(8) 0.0202(7) 0.0018(5) 0.0019(6) -0.0012(6) C4 0.0229(10) 0.0188(8) 0.0183(8) -0.0032(6) 0.0000(6) -0.0015(7) N2B 0.0177(9) 0.0388(9) 0.0281(8) 0.0064(6) 0.0037(6) 0.0031(7) C6 0.0225(9) 0.0229(9) 0.0244(8) -0.0023(6) -0.0030(7) -0.0006(7) C7 0.0199(10) 0.0226(9) 0.0183(8) -0.0048(6) -0.0018(7) -0.0021(8) C8 0.0335(11) 0.0248(9) 0.0228(8) 0.0030(6) -0.0060(7) -0.0026(8) C9 0.0235(10) 0.0274(10) 0.0232(8) -0.0040(7) 0.0064(7) -0.0045(8) C10 0.0221(10) 0.0245(9) 0.0284(9) -0.0021(7) 0.0007(7) 0.0011(8) C11 0.0197(9) 0.0258(10) 0.0213(8) -0.0035(7) 0.0015(7) -0.0044(7) C12 0.0226(10) 0.0248(9) 0.0276(9) 0.0032(7) -0.0001(7) 0.0028(8) C13 0.0359(11) 0.0241(9) 0.0228(8) 0.0014(7) 0.0039(7) -0.0056(8) C14 0.0368(11) 0.0219(9) 0.0225(8) 0.0012(6) 0.0029(7) -0.0038(8) C15 0.0281(10) 0.0256(10) 0.0320(9) 0.0015(7) 0.0094(7) 0.0013(8) C16 0.0314(11) 0.0260(10) 0.0265(9) 0.0040(7) -0.0016(7) -0.0011(8) _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 O1A C7 1.2765(18) . ? O2A C7 1.2510(19) . ? N1B C11 1.347(2) . ? N1B C10 1.360(2) . ? N1B H1 0.992(19) . ? C4 C12 1.386(2) . ? C4 C6 1.395(2) . ? C4 C7 1.503(2) . ? N2B C11 1.337(2) . ? N2B H5 0.97(2) . ? N2B H7 0.93(2) . ? C6 C8 1.385(2) . ? C6 H6 0.9500 . ? C8 C14 1.385(2) . ? C8 H8 0.9500 . ? C9 C13 1.365(2) . ? C9 C11 1.415(2) . ? C9 H9 0.9500 . ? C10 C16 1.359(2) . ? C10 H10 0.9500 . ? C12 C15 1.393(2) . ? C12 H12 0.9500 . ? C13 C16 1.398(2) . ? C13 H13 0.9500 . ? C14 C15 1.381(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 N1B C10 121.88(14) . . ? C11 N1B H1 122.3(11) . . ? C10 N1B H1 115.8(12) . . ? C12 C4 C6 118.83(13) . . ? C12 C4 C7 121.60(13) . . ? C6 C4 C7 119.55(14) . . ? C11 N2B H5 118.8(12) . . ? C11 N2B H7 117.5(11) . . ? H5 N2B H7 123.6(16) . . ? C8 C6 C4 120.65(15) . . ? C8 C6 H6 119.7 . . ? C4 C6 H6 119.7 . . ? O2A C7 O1A 124.16(14) . . ? O2A C7 C4 118.20(14) . . ? O1A C7 C4 117.64(14) . . ? C14 C8 C6 120.00(15) . . ? C14 C8 H8 120.0 . . ? C6 C8 H8 120.0 . . ? C13 C9 C11 119.28(16) . . ? C13 C9 H9 120.4 . . ? C11 C9 H9 120.4 . . ? C16 C10 N1B 121.31(16) . . ? C16 C10 H10 119.3 . . ? N1B C10 H10 119.3 . . ? N2B C11 N1B 118.37(14) . . ? N2B C11 C9 123.18(15) . . ? N1B C11 C9 118.45(15) . . ? C4 C12 C15 120.53(15) . . ? C4 C12 H12 119.7 . . ? C15 C12 H12 119.7 . . ? C9 C13 C16 120.99(15) . . ? C9 C13 H13 119.5 . . ? C16 C13 H13 119.5 . . ? C15 C14 C8 119.93(15) . . ? C15 C14 H14 120.0 . . ? C8 C14 H14 120.0 . . ? C14 C15 C12 120.06(16) . . ? C14 C15 H15 120.0 . . ? C12 C15 H15 120.0 . . ? C10 C16 C13 118.06(16) . . ? C10 C16 H16 121.0 . . ? C13 C16 H16 121.0 . . ? 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 C12 C4 C6 C8 -0.2(2) . . . . ? C7 C4 C6 C8 178.22(13) . . . . ? C12 C4 C7 O2A 174.31(14) . . . . ? C6 C4 C7 O2A -4.1(2) . . . . ? C12 C4 C7 O1A -4.9(2) . . . . ? C6 C4 C7 O1A 176.68(13) . . . . ? C4 C6 C8 C14 0.1(2) . . . . ? C11 N1B C10 C16 0.5(2) . . . . ? C10 N1B C11 N2B 178.73(14) . . . . ? C10 N1B C11 C9 -1.4(2) . . . . ? C13 C9 C11 N2B -179.28(15) . . . . ? C13 C9 C11 N1B 0.9(2) . . . . ? C6 C4 C12 C15 0.5(2) . . . . ? C7 C4 C12 C15 -177.94(14) . . . . ? C11 C9 C13 C16 0.6(2) . . . . ? C6 C8 C14 C15 -0.1(2) . . . . ? C8 C14 C15 C12 0.4(2) . . . . ? C4 C12 C15 C14 -0.6(2) . . . . ? N1B C10 C16 C13 1.0(2) . . . . ? C9 C13 C16 C10 -1.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.219 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 963014' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(VIII)-CCDC963015 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-bromobenzoic acid + 2-aminopyridine ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C7 H4 Br O2, C5 H7 N2' _chemical_formula_sum 'C12 H11 Br N2 O2' _chemical_formula_weight 295.14 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' Br Br -0.2901 2.4595 '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 9.6861(7) _cell_length_b 10.3327(7) _cell_length_c 12.0022(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.765(2) _cell_angle_gamma 90.00 _cell_volume 1190.21(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 18549 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 26.43 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.647 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 3.444 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5458 _exptl_absorpt_correction_T_max 0.6442 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Bruker Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18549 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.43 _reflns_number_total 2439 _reflns_number_gt 2182 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0227P)^2^+0.6440P] 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 0 _refine_ls_number_reflns 2439 _refine_ls_number_parameters 198 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0208 _refine_ls_wR_factor_ref 0.0533 _refine_ls_wR_factor_gt 0.0515 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.052 _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 Br1 Br -0.043454(19) 0.34763(2) 0.272345(16) 0.03741(8) Uani 1 1 d . . . O1A O 0.43045(13) -0.13695(12) 0.43136(9) 0.0277(3) Uani 1 1 d . . . O2A O 0.31085(15) -0.13215(14) 0.57726(10) 0.0368(3) Uani 1 1 d . . . C4 C 0.07913(18) 0.21826(18) 0.34019(15) 0.0273(4) Uani 1 1 d . . . C5 C 0.17891(19) 0.16792(18) 0.28079(15) 0.0283(4) Uani 1 1 d . . . C6 C 0.25293(16) 0.02298(17) 0.43502(13) 0.0230(3) Uani 1 1 d . . . C9 C 0.0656(2) 0.17506(19) 0.44741(16) 0.0321(4) Uani 1 1 d . . . C10 C 0.56183(18) -0.37170(18) 0.64948(14) 0.0277(4) Uani 1 1 d . . . C11 C 0.33867(17) -0.08983(17) 0.48526(13) 0.0247(3) Uani 1 1 d . . . N2B N 0.47626(18) -0.30737(17) 0.70726(13) 0.0337(4) Uani 1 1 d D . . C13 C 0.26631(18) 0.07035(18) 0.32858(14) 0.0255(4) Uani 1 1 d . . . C14 C 0.15326(18) 0.07778(18) 0.49389(15) 0.0286(4) Uani 1 1 d . . . C15 C 0.65312(19) -0.3961(2) 0.47694(16) 0.0326(4) Uani 1 1 d . . . C17 C 0.7338(2) -0.4964(2) 0.5159(2) 0.0426(5) Uani 1 1 d . . . C18 C 0.7297(2) -0.5369(2) 0.6273(2) 0.0447(5) Uani 1 1 d . . . N1B N 0.56955(15) -0.33475(15) 0.54238(12) 0.0253(3) Uani 1 1 d . . . C2 C 0.6462(2) -0.4760(2) 0.69318(17) 0.0365(4) Uani 1 1 d . . . H1 H 0.144(2) 0.042(2) 0.5642(17) 0.034(5) Uiso 1 1 d . . . H2 H 0.647(2) -0.361(2) 0.4026(19) 0.039(6) Uiso 1 1 d . . . H3 H -0.004(2) 0.207(2) 0.4854(18) 0.038(5) Uiso 1 1 d . . . H4 H 0.188(2) 0.201(2) 0.2097(18) 0.039(6) Uiso 1 1 d . . . H5 H 0.335(2) 0.038(2) 0.2910(17) 0.037(6) Uiso 1 1 d . . . H6 H 0.641(2) -0.500(2) 0.7663(19) 0.041(6) Uiso 1 1 d . . . H7 H 0.519(2) -0.267(2) 0.5114(18) 0.040(6) Uiso 1 1 d . . . H8 H 0.464(2) -0.339(2) 0.7790(15) 0.051(7) Uiso 1 1 d D . . H9 H 0.413(2) -0.244(2) 0.6677(19) 0.057(7) Uiso 1 1 d D . . H10 H 0.778(2) -0.606(3) 0.6566(19) 0.048(7) Uiso 1 1 d . . . H11 H 0.787(3) -0.540(3) 0.470(2) 0.057(7) 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 Br1 0.03310(11) 0.03603(13) 0.04267(12) 0.00764(8) 0.00357(8) 0.00999(8) O1A 0.0340(6) 0.0296(7) 0.0202(6) 0.0003(5) 0.0060(5) 0.0065(5) O2A 0.0481(8) 0.0392(8) 0.0257(6) 0.0088(6) 0.0142(6) 0.0113(6) C4 0.0253(8) 0.0247(10) 0.0308(9) 0.0019(7) 0.0000(7) 0.0012(7) C5 0.0322(9) 0.0282(10) 0.0248(8) 0.0035(7) 0.0046(7) 0.0008(7) C6 0.0240(8) 0.0232(9) 0.0215(8) -0.0027(6) 0.0017(6) -0.0039(7) C9 0.0295(9) 0.0349(11) 0.0335(9) -0.0012(8) 0.0104(7) 0.0050(8) C10 0.0326(9) 0.0266(10) 0.0226(8) 0.0025(7) -0.0008(7) -0.0082(7) C11 0.0297(8) 0.0243(9) 0.0197(8) -0.0022(7) 0.0021(6) -0.0022(7) N2B 0.0444(9) 0.0371(10) 0.0208(7) 0.0059(7) 0.0080(7) -0.0009(8) C13 0.0272(8) 0.0263(10) 0.0238(8) -0.0003(7) 0.0064(7) 0.0005(7) C14 0.0313(9) 0.0314(11) 0.0238(9) 0.0014(7) 0.0068(7) 0.0014(8) C15 0.0320(9) 0.0353(11) 0.0314(10) -0.0053(8) 0.0072(8) -0.0043(8) C17 0.0349(10) 0.0373(12) 0.0557(13) -0.0101(10) 0.0069(9) 0.0026(9) C18 0.0376(11) 0.0295(12) 0.0627(14) 0.0050(10) -0.0084(10) 0.0022(9) N1B 0.0291(7) 0.0249(8) 0.0217(7) 0.0025(6) 0.0030(6) -0.0008(6) C2 0.0404(11) 0.0320(11) 0.0334(10) 0.0093(8) -0.0082(8) -0.0064(9) _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 Br1 C4 1.8970(18) . ? O1A C11 1.265(2) . ? O2A C11 1.250(2) . ? C4 C5 1.378(2) . ? C4 C9 1.385(3) . ? C5 C13 1.390(3) . ? C5 H4 0.93(2) . ? C6 C13 1.390(2) . ? C6 C14 1.391(2) . ? C6 C11 1.509(2) . ? C9 C14 1.384(3) . ? C9 H3 0.92(2) . ? C10 N2B 1.328(2) . ? C10 N1B 1.353(2) . ? C10 C2 1.410(3) . ? N2B H8 0.941(16) . ? N2B H9 0.971(17) . ? C13 H5 0.92(2) . ? C14 H1 0.93(2) . ? C15 C17 1.343(3) . ? C15 N1B 1.359(2) . ? C15 H2 0.96(2) . ? C17 C18 1.407(3) . ? C17 H11 0.92(3) . ? C18 C2 1.360(3) . ? C18 H10 0.90(3) . ? N1B H7 0.90(2) . ? C2 H6 0.92(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 C5 C4 C9 121.34(17) . . ? C5 C4 Br1 119.07(13) . . ? C9 C4 Br1 119.58(13) . . ? C4 C5 C13 119.41(16) . . ? C4 C5 H4 119.5(13) . . ? C13 C5 H4 121.1(13) . . ? C13 C6 C14 118.72(16) . . ? C13 C6 C11 121.64(15) . . ? C14 C6 C11 119.58(15) . . ? C14 C9 C4 118.60(17) . . ? C14 C9 H3 120.7(13) . . ? C4 C9 H3 120.6(13) . . ? N2B C10 N1B 118.25(16) . . ? N2B C10 C2 124.00(17) . . ? N1B C10 C2 117.75(17) . . ? O2A C11 O1A 124.54(17) . . ? O2A C11 C6 116.77(15) . . ? O1A C11 C6 118.67(14) . . ? C10 N2B H8 118.0(14) . . ? C10 N2B H9 118.4(15) . . ? H8 N2B H9 122(2) . . ? C5 C13 C6 120.50(16) . . ? C5 C13 H5 120.3(13) . . ? C6 C13 H5 119.2(13) . . ? C9 C14 C6 121.40(16) . . ? C9 C14 H1 121.4(13) . . ? C6 C14 H1 117.1(13) . . ? C17 C15 N1B 121.54(19) . . ? C17 C15 H2 125.2(13) . . ? N1B C15 H2 113.3(13) . . ? C15 C17 C18 118.1(2) . . ? C15 C17 H11 121.0(16) . . ? C18 C17 H11 120.9(16) . . ? C2 C18 C17 120.7(2) . . ? C2 C18 H10 117.5(15) . . ? C17 C18 H10 121.8(15) . . ? C10 N1B C15 122.09(17) . . ? C10 N1B H7 120.8(14) . . ? C15 N1B H7 117.2(14) . . ? C18 C2 C10 119.86(19) . . ? C18 C2 H6 122.8(14) . . ? C10 C2 H6 117.4(14) . . ? 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 C9 C4 C5 C13 1.1(3) . . . . ? Br1 C4 C5 C13 -178.06(14) . . . . ? C5 C4 C9 C14 -1.1(3) . . . . ? Br1 C4 C9 C14 178.00(14) . . . . ? C13 C6 C11 O2A -174.18(16) . . . . ? C14 C6 C11 O2A 2.8(2) . . . . ? C13 C6 C11 O1A 4.2(2) . . . . ? C14 C6 C11 O1A -178.80(16) . . . . ? C4 C5 C13 C6 0.5(3) . . . . ? C14 C6 C13 C5 -1.9(3) . . . . ? C11 C6 C13 C5 175.16(16) . . . . ? C4 C9 C14 C6 -0.4(3) . . . . ? C13 C6 C14 C9 1.8(3) . . . . ? C11 C6 C14 C9 -175.26(17) . . . . ? N1B C15 C17 C18 0.1(3) . . . . ? C15 C17 C18 C2 0.0(3) . . . . ? N2B C10 N1B C15 -179.23(16) . . . . ? C2 C10 N1B C15 1.2(3) . . . . ? C17 C15 N1B C10 -0.7(3) . . . . ? C17 C18 C2 C10 0.5(3) . . . . ? N2B C10 C2 C18 179.34(19) . . . . ? N1B C10 C2 C18 -1.1(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.262 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 963015' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(IX)-CCDC963016 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-aminobenzoic acid + 2-amino-4-methylpyridine ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C7 H6 N O2, C6 H9 N2' _chemical_formula_sum 'C13 H15 N3 O2' _chemical_formula_weight 245.28 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 P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.5541(11) _cell_length_b 8.5531(17) _cell_length_c 25.380(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1205.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2199 _cell_measurement_theta_min 4.38 _cell_measurement_theta_max 25.34 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9815 _exptl_absorpt_correction_T_max 0.9833 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Bruker Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2199 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0867 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 4.38 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2199 _reflns_number_gt 1468 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0320P)^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 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration unknown _refine_ls_number_reflns 2199 _refine_ls_number_parameters 184 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.941 _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 O2A O 0.5698(3) 0.86700(17) 0.07743(6) 0.0308(4) Uani 1 1 d . . . O1A O 0.7620(3) 0.81044(17) 0.15245(5) 0.0265(4) Uani 1 1 d . . . C3A C 0.5973(4) 0.8806(2) 0.12663(9) 0.0230(5) Uani 1 1 d . . . C4A C 0.4332(4) 0.9854(2) 0.15702(9) 0.0212(5) Uani 1 1 d . . . N2B N 0.9286(4) 0.6705(2) 0.02920(8) 0.0293(5) Uani 1 1 d D . . N1B N 1.0800(4) 0.6225(2) 0.11195(7) 0.0237(5) Uani 1 1 d . . . C7A C 0.1290(4) 1.1839(3) 0.21554(9) 0.0230(6) Uani 1 1 d . . . N1A N -0.0194(4) 1.2786(3) 0.24560(9) 0.0321(5) Uani 1 1 d . . . C9A C 0.4898(4) 1.0291(3) 0.20855(9) 0.0232(6) Uani 1 1 d . . . H9A H 0.6330 0.9897 0.2242 0.028 Uiso 1 1 calc R . . C3B C 1.0921(4) 0.5987(2) 0.05945(9) 0.0224(6) Uani 1 1 d . . . C5A C 0.2214(4) 1.0443(3) 0.13565(9) 0.0257(6) Uani 1 1 d . . . H5A H 0.1789 1.0177 0.1005 0.031 Uiso 1 1 calc R . . C5B C 1.4301(4) 0.4262(2) 0.07294(9) 0.0247(6) Uani 1 1 d . . . C4B C 1.2716(4) 0.4998(3) 0.03975(9) 0.0241(5) Uani 1 1 d . . . H4B H 1.2839 0.4834 0.0028 0.029 Uiso 1 1 calc R . . C8A C 0.3446(4) 1.1274(3) 0.23746(9) 0.0248(6) Uani 1 1 d . . . H8A H 0.3900 1.1570 0.2721 0.030 Uiso 1 1 calc R . . C6A C 0.0714(4) 1.1408(2) 0.16445(8) 0.0262(6) Uani 1 1 d . . . H6A H -0.0733 1.1781 0.1490 0.031 Uiso 1 1 calc R . . C7B C 1.2378(4) 0.5522(3) 0.14520(9) 0.0287(6) Uani 1 1 d . . . H7B H 1.2258 0.5716 0.1820 0.034 Uiso 1 1 calc R . . C6B C 1.4123(4) 0.4549(3) 0.12723(9) 0.0290(6) Uani 1 1 d . . . H6B H 1.5212 0.4068 0.1511 0.035 Uiso 1 1 calc R . . C8B C 1.6145(4) 0.3146(3) 0.05230(9) 0.0331(6) Uani 1 1 d . . . H9B H 1.7726 0.3411 0.0670 0.050 Uiso 1 1 calc R . . H10B H 1.6206 0.3218 0.0138 0.050 Uiso 1 1 calc R . . H8B H 1.5713 0.2078 0.0626 0.050 Uiso 1 1 calc R . . H3B H 0.929(4) 0.654(2) -0.0097(6) 0.052(8) Uiso 1 1 d D . . H1B H 0.947(4) 0.693(3) 0.1256(8) 0.037(6) Uiso 1 1 d . . . H10A H -0.150(5) 1.328(3) 0.2288(10) 0.058(9) Uiso 1 1 d . . . H2B H 0.804(4) 0.736(3) 0.0429(9) 0.050(8) Uiso 1 1 d . . . H11A H 0.044(5) 1.321(3) 0.2771(11) 0.063(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 O2A 0.0358(10) 0.0418(9) 0.0150(9) -0.0033(7) -0.0002(8) 0.0049(9) O1A 0.0280(9) 0.0293(8) 0.0221(9) -0.0018(8) 0.0008(8) 0.0049(9) C3A 0.0245(14) 0.0215(13) 0.0230(14) -0.0017(11) 0.0023(12) -0.0083(12) C4A 0.0238(12) 0.0216(12) 0.0183(13) 0.0011(10) 0.0033(12) -0.0008(12) N2B 0.0320(12) 0.0382(13) 0.0178(12) 0.0006(10) -0.0009(11) 0.0087(12) N1B 0.0255(11) 0.0259(11) 0.0198(12) -0.0012(9) 0.0038(10) 0.0014(10) C7A 0.0256(14) 0.0221(13) 0.0213(14) 0.0003(11) 0.0024(11) -0.0043(12) N1A 0.0287(12) 0.0382(13) 0.0293(13) -0.0069(11) -0.0038(11) 0.0097(11) C9A 0.0223(13) 0.0260(12) 0.0213(14) 0.0009(12) -0.0005(11) -0.0004(11) C3B 0.0243(14) 0.0211(12) 0.0218(14) -0.0007(10) 0.0002(11) -0.0035(13) C5A 0.0291(14) 0.0276(13) 0.0205(14) 0.0006(10) -0.0015(12) -0.0032(13) C5B 0.0242(13) 0.0231(13) 0.0268(15) -0.0003(10) 0.0012(12) -0.0032(12) C4B 0.0273(13) 0.0268(13) 0.0183(13) -0.0024(10) 0.0026(12) -0.0038(13) C8A 0.0262(14) 0.0321(13) 0.0161(13) -0.0024(11) 0.0003(11) -0.0006(12) C6A 0.0237(13) 0.0297(13) 0.0254(14) 0.0033(11) -0.0024(12) -0.0012(13) C7B 0.0330(14) 0.0347(14) 0.0183(14) 0.0017(11) -0.0010(13) -0.0008(15) C6B 0.0318(14) 0.0316(14) 0.0236(14) 0.0036(11) -0.0047(13) 0.0042(14) C8B 0.0329(14) 0.0311(14) 0.0351(15) 0.0012(12) 0.0008(12) 0.0039(14) _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 O2A C3A 1.263(2) . ? O1A C3A 1.275(3) . ? C3A C4A 1.493(3) . ? C4A C5A 1.390(3) . ? C4A C9A 1.396(3) . ? N2B C3B 1.339(3) . ? N2B H3B 0.996(16) . ? N2B H2B 0.96(3) . ? N1B C3B 1.349(3) . ? N1B C7B 1.357(3) . ? N1B H1B 1.02(2) . ? C7A N1A 1.385(3) . ? C7A C6A 1.386(3) . ? C7A C8A 1.406(3) . ? N1A H10A 0.94(3) . ? N1A H11A 0.95(3) . ? C9A C8A 1.377(3) . ? C9A H9A 0.9500 . ? C3B C4B 1.400(3) . ? C5A C6A 1.382(3) . ? C5A H5A 0.9500 . ? C5B C4B 1.372(3) . ? C5B C6B 1.403(3) . ? C5B C8B 1.494(3) . ? C4B H4B 0.9500 . ? C8A H8A 0.9500 . ? C6A H6A 0.9500 . ? C7B C6B 1.356(3) . ? C7B H7B 0.9500 . ? C6B H6B 0.9500 . ? C8B H9B 0.9800 . ? C8B H10B 0.9800 . ? C8B H8B 0.9800 . ? 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 O2A C3A O1A 123.5(2) . . ? O2A C3A C4A 119.5(2) . . ? O1A C3A C4A 117.1(2) . . ? C5A C4A C9A 117.3(2) . . ? C5A C4A C3A 122.2(2) . . ? C9A C4A C3A 120.5(2) . . ? C3B N2B H3B 120.3(13) . . ? C3B N2B H2B 123.5(14) . . ? H3B N2B H2B 116(2) . . ? C3B N1B C7B 121.0(2) . . ? C3B N1B H1B 117.5(12) . . ? C7B N1B H1B 121.4(12) . . ? N1A C7A C6A 122.3(2) . . ? N1A C7A C8A 119.3(2) . . ? C6A C7A C8A 118.4(2) . . ? C7A N1A H10A 118.1(16) . . ? C7A N1A H11A 118.0(16) . . ? H10A N1A H11A 120(2) . . ? C8A C9A C4A 122.1(2) . . ? C8A C9A H9A 119.0 . . ? C4A C9A H9A 119.0 . . ? N2B C3B N1B 117.6(2) . . ? N2B C3B C4B 123.8(2) . . ? N1B C3B C4B 118.6(2) . . ? C6A C5A C4A 121.4(2) . . ? C6A C5A H5A 119.3 . . ? C4A C5A H5A 119.3 . . ? C4B C5B C6B 118.5(2) . . ? C4B C5B C8B 121.2(2) . . ? C6B C5B C8B 120.3(2) . . ? C5B C4B C3B 121.0(2) . . ? C5B C4B H4B 119.5 . . ? C3B C4B H4B 119.5 . . ? C9A C8A C7A 119.9(2) . . ? C9A C8A H8A 120.1 . . ? C7A C8A H8A 120.1 . . ? C5A C6A C7A 121.0(2) . . ? C5A C6A H6A 119.5 . . ? C7A C6A H6A 119.5 . . ? C6B C7B N1B 121.6(2) . . ? C6B C7B H7B 119.2 . . ? N1B C7B H7B 119.2 . . ? C7B C6B C5B 119.2(2) . . ? C7B C6B H6B 120.4 . . ? C5B C6B H6B 120.4 . . ? C5B C8B H9B 109.5 . . ? C5B C8B H10B 109.5 . . ? H9B C8B H10B 109.5 . . ? C5B C8B H8B 109.5 . . ? H9B C8B H8B 109.5 . . ? H10B C8B H8B 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2A C3A C4A C5A 13.4(3) . . . . ? O1A C3A C4A C5A -167.54(19) . . . . ? O2A C3A C4A C9A -166.1(2) . . . . ? O1A C3A C4A C9A 13.0(3) . . . . ? C5A C4A C9A C8A -0.5(3) . . . . ? C3A C4A C9A C8A 179.01(19) . . . . ? C7B N1B C3B N2B 179.2(2) . . . . ? C7B N1B C3B C4B -0.1(3) . . . . ? C9A C4A C5A C6A -0.7(3) . . . . ? C3A C4A C5A C6A 179.8(2) . . . . ? C6B C5B C4B C3B -1.5(3) . . . . ? C8B C5B C4B C3B 177.1(2) . . . . ? N2B C3B C4B C5B -178.2(2) . . . . ? N1B C3B C4B C5B 1.0(3) . . . . ? C4A C9A C8A C7A 1.5(3) . . . . ? N1A C7A C8A C9A 177.9(2) . . . . ? C6A C7A C8A C9A -1.3(3) . . . . ? C4A C5A C6A C7A 0.9(3) . . . . ? N1A C7A C6A C5A -179.1(2) . . . . ? C8A C7A C6A C5A 0.2(3) . . . . ? C3B N1B C7B C6B -0.4(3) . . . . ? N1B C7B C6B C5B 0.0(3) . . . . ? C4B C5B C6B C7B 1.0(3) . . . . ? C8B C5B C6B C7B -177.59(19) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.163 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 963016' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(X)-CCDC963017 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-methoxybenzoic acid + 2-amino-6-methylpyridine ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C8 H7 O3, C6 H9 N2' _chemical_formula_sum 'C14 H16 N2 O3' _chemical_formula_weight 260.29 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 9.4403(19) _cell_length_b 11.509(2) _cell_length_c 12.690(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.77(3) _cell_angle_gamma 90.00 _cell_volume 1289.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4578 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 25.37 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9821 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4578 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0692 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.37 _reflns_number_total 2355 _reflns_number_gt 1445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0443P)^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 0 _refine_ls_number_reflns 2355 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 O3A O 0.06964(14) 0.14097(11) 0.81390(10) 0.0274(3) Uani 1 1 d . . . O1A O 0.74031(15) 0.27837(11) 0.85823(11) 0.0261(3) Uani 1 1 d . . . O2A O 0.78419(15) 0.19748(11) 1.02678(11) 0.0301(4) Uani 1 1 d . . . N1B N 1.02563(18) 0.36409(12) 0.94414(13) 0.0203(4) Uani 1 1 d . . . N2B N 1.0832(2) 0.26625(14) 1.11324(15) 0.0268(4) Uani 1 1 d . . . C6 C 0.2686(2) 0.23790(15) 0.78147(15) 0.0226(5) Uani 1 1 d . . . H6 H 0.1962 0.2705 0.7155 0.027 Uiso 1 1 calc R . . C7 C 0.5295(2) 0.21589(15) 0.90570(15) 0.0196(4) Uani 1 1 d . . . C8 C 0.2216(2) 0.16493(15) 0.85025(15) 0.0211(4) Uani 1 1 d . . . C9 C 0.3268(2) 0.12006(15) 0.94805(15) 0.0234(5) Uani 1 1 d . . . H9 H 0.2951 0.0717 0.9962 0.028 Uiso 1 1 calc R . . C10 C 1.1256(2) 0.34007(15) 1.04877(15) 0.0214(5) Uani 1 1 d . . . C11 C 1.2685(2) 0.39394(16) 1.08314(17) 0.0262(5) Uani 1 1 d . . . H11 H 1.3428 0.3764 1.1545 0.031 Uiso 1 1 calc R . . C12 C 1.1933(2) 0.49497(16) 0.90555(17) 0.0282(5) Uani 1 1 d . . . H12 H 1.2156 0.5493 0.8573 0.034 Uiso 1 1 calc R . . C13 C 0.4790(2) 0.14649(15) 0.97485(15) 0.0231(5) Uani 1 1 d . . . H13 H 0.5508 0.1163 1.0424 0.028 Uiso 1 1 calc R . . C14 C 1.0579(2) 0.43866(16) 0.87155(15) 0.0237(5) Uani 1 1 d . . . C15 C 0.6961(2) 0.23178(15) 0.93259(16) 0.0231(5) Uani 1 1 d . . . C16 C 1.2995(2) 0.47162(17) 1.01309(17) 0.0307(5) Uani 1 1 d . . . H16 H 1.3945 0.5105 1.0374 0.037 Uiso 1 1 calc R . . C17 C 0.4207(2) 0.26283(15) 0.80945(16) 0.0220(5) Uani 1 1 d . . . H17 H 0.4519 0.3129 0.7623 0.026 Uiso 1 1 calc R . . C18 C 0.9384(2) 0.44927(17) 0.75726(16) 0.0320(5) Uani 1 1 d . . . H18A H 0.9637 0.5135 0.7164 0.048 Uiso 1 1 calc R . . H18B H 0.8404 0.4645 0.7649 0.048 Uiso 1 1 calc R . . H18C H 0.9327 0.3767 0.7155 0.048 Uiso 1 1 calc R . . C19 C 0.0202(2) 0.06185(17) 0.88146(17) 0.0311(5) Uani 1 1 d . . . H19A H 0.0726 -0.0126 0.8868 0.047 Uiso 1 1 calc R . . H19B H -0.0893 0.0498 0.8465 0.047 Uiso 1 1 calc R . . H19C H 0.0437 0.0944 0.9571 0.047 Uiso 1 1 calc R . . H1 H 0.975(3) 0.2415(17) 1.0818(18) 0.043(6) Uiso 1 1 d . . . H2 H 0.921(2) 0.3255(15) 0.9158(16) 0.035(6) Uiso 1 1 d . . . H3 H 1.143(3) 0.2546(17) 1.1878(19) 0.048(7) 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 O3A 0.0206(8) 0.0336(8) 0.0264(8) 0.0025(6) 0.0065(6) -0.0036(6) O1A 0.0239(8) 0.0323(8) 0.0223(8) -0.0003(6) 0.0086(6) -0.0035(6) O2A 0.0235(8) 0.0378(8) 0.0256(8) 0.0048(6) 0.0046(7) -0.0019(6) N1B 0.0196(10) 0.0208(9) 0.0209(9) -0.0001(7) 0.0076(8) 0.0003(7) N2B 0.0230(11) 0.0342(10) 0.0189(10) 0.0032(8) 0.0024(9) -0.0026(8) C6 0.0231(12) 0.0249(11) 0.0188(10) 0.0009(8) 0.0063(9) 0.0037(8) C7 0.0204(11) 0.0205(10) 0.0186(10) -0.0026(8) 0.0077(9) -0.0003(8) C8 0.0186(12) 0.0229(10) 0.0220(11) -0.0057(8) 0.0074(9) -0.0006(8) C9 0.0241(12) 0.0263(11) 0.0205(11) 0.0018(9) 0.0089(9) -0.0028(9) C10 0.0215(12) 0.0218(10) 0.0206(11) -0.0018(8) 0.0070(9) 0.0021(8) C11 0.0200(12) 0.0310(11) 0.0257(11) -0.0059(9) 0.0058(9) -0.0008(9) C12 0.0318(13) 0.0244(11) 0.0340(13) -0.0011(9) 0.0187(11) -0.0032(9) C13 0.0249(12) 0.0247(11) 0.0172(10) -0.0017(8) 0.0043(9) -0.0003(9) C14 0.0286(12) 0.0224(10) 0.0232(11) -0.0004(9) 0.0128(10) 0.0045(9) C15 0.0270(12) 0.0204(10) 0.0207(11) -0.0039(9) 0.0070(10) -0.0005(8) C16 0.0251(12) 0.0319(12) 0.0374(13) -0.0097(10) 0.0141(11) -0.0051(9) C17 0.0259(12) 0.0204(10) 0.0222(11) -0.0003(8) 0.0114(9) 0.0010(8) C18 0.0388(14) 0.0327(12) 0.0266(12) 0.0043(10) 0.0142(11) 0.0025(10) C19 0.0255(12) 0.0349(12) 0.0324(12) 0.0047(10) 0.0098(10) -0.0059(9) _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 O3A C8 1.370(2) . ? O3A C19 1.437(2) . ? O1A C15 1.277(2) . ? O2A C15 1.253(2) . ? N1B C10 1.357(2) . ? N1B C14 1.370(2) . ? N1B H2 1.03(2) . ? N2B C10 1.335(2) . ? N2B H1 1.00(2) . ? N2B H3 0.92(2) . ? C6 C17 1.382(3) . ? C6 C8 1.392(2) . ? C6 H6 0.9500 . ? C7 C13 1.390(2) . ? C7 C17 1.396(3) . ? C7 C15 1.498(3) . ? C8 C9 1.385(3) . ? C9 C13 1.388(3) . ? C9 H9 0.9500 . ? C10 C11 1.407(3) . ? C11 C16 1.364(3) . ? C11 H11 0.9500 . ? C12 C14 1.359(3) . ? C12 C16 1.404(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C18 1.494(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 C8 O3A C19 116.69(15) . . ? C10 N1B C14 122.84(17) . . ? C10 N1B H2 120.2(10) . . ? C14 N1B H2 116.9(10) . . ? C10 N2B H1 115.1(12) . . ? C10 N2B H3 121.0(14) . . ? H1 N2B H3 122.1(18) . . ? C17 C6 C8 119.80(18) . . ? C17 C6 H6 120.1 . . ? C8 C6 H6 120.1 . . ? C13 C7 C17 117.68(17) . . ? C13 C7 C15 119.57(17) . . ? C17 C7 C15 122.65(16) . . ? O3A C8 C9 123.98(16) . . ? O3A C8 C6 116.00(17) . . ? C9 C8 C6 120.02(18) . . ? C8 C9 C13 119.26(17) . . ? C8 C9 H9 120.4 . . ? C13 C9 H9 120.4 . . ? N2B C10 N1B 118.28(18) . . ? N2B C10 C11 123.59(19) . . ? N1B C10 C11 118.13(18) . . ? C16 C11 C10 119.4(2) . . ? C16 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C14 C12 C16 118.99(19) . . ? C14 C12 H12 120.5 . . ? C16 C12 H12 120.5 . . ? C9 C13 C7 121.87(18) . . ? C9 C13 H13 119.1 . . ? C7 C13 H13 119.1 . . ? C12 C14 N1B 119.56(18) . . ? C12 C14 C18 124.80(18) . . ? N1B C14 C18 115.62(17) . . ? O2A C15 O1A 123.82(19) . . ? O2A C15 C7 117.84(17) . . ? O1A C15 C7 118.34(17) . . ? C11 C16 C12 120.98(19) . . ? C11 C16 H16 119.5 . . ? C12 C16 H16 119.5 . . ? C6 C17 C7 121.31(17) . . ? C6 C17 H17 119.3 . . ? C7 C17 H17 119.3 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O3A C19 H19A 109.5 . . ? O3A C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3A C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C19 O3A C8 C9 -1.7(2) . . . . ? C19 O3A C8 C6 177.44(16) . . . . ? C17 C6 C8 O3A -177.40(15) . . . . ? C17 C6 C8 C9 1.8(3) . . . . ? O3A C8 C9 C13 177.56(15) . . . . ? C6 C8 C9 C13 -1.5(3) . . . . ? C14 N1B C10 N2B 179.91(16) . . . . ? C14 N1B C10 C11 -0.4(2) . . . . ? N2B C10 C11 C16 -177.48(17) . . . . ? N1B C10 C11 C16 2.8(3) . . . . ? C8 C9 C13 C7 -0.7(3) . . . . ? C17 C7 C13 C9 2.6(3) . . . . ? C15 C7 C13 C9 -173.85(16) . . . . ? C16 C12 C14 N1B 2.6(3) . . . . ? C16 C12 C14 C18 -176.02(18) . . . . ? C10 N1B C14 C12 -2.3(3) . . . . ? C10 N1B C14 C18 176.37(16) . . . . ? C13 C7 C15 O2A -11.5(2) . . . . ? C17 C7 C15 O2A 172.26(16) . . . . ? C13 C7 C15 O1A 167.88(16) . . . . ? C17 C7 C15 O1A -8.3(3) . . . . ? C10 C11 C16 C12 -2.6(3) . . . . ? C14 C12 C16 C11 -0.1(3) . . . . ? C8 C6 C17 C7 0.2(3) . . . . ? C13 C7 C17 C6 -2.3(3) . . . . ? C15 C7 C17 C6 173.97(16) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.187 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 963017' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(XI)-CCDC963018 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-methoxybenzoic acid + 2-amino-4-methylpyridine ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C8 H7 O3, C6 H9 N2' _chemical_formula_sum 'C14 H16 N2 O3' _chemical_formula_weight 260.29 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/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 10.337(2) _cell_length_b 11.727(2) _cell_length_c 11.031(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.53(3) _cell_angle_gamma 90.00 _cell_volume 1288.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5041 _cell_measurement_theta_min 3.47 _cell_measurement_theta_max 27.89 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9784 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5041 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0851 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 27.89 _reflns_number_total 2887 _reflns_number_gt 1640 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0632P)^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 0 _refine_ls_number_reflns 2887 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1040 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1209 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _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 O1A O 0.90723(11) 0.11980(8) 0.92411(11) 0.0235(3) Uani 1 1 d . . . O2A O 0.81293(12) 0.12610(9) 1.08405(11) 0.0301(3) Uani 1 1 d . . . C5 C 0.75132(16) -0.02609(12) 0.93936(15) 0.0178(4) Uani 1 1 d . . . C6 C 0.65592(16) -0.06522(13) 0.99689(15) 0.0206(4) Uani 1 1 d . . . H6 H 0.6446 -0.0263 1.0689 0.025 Uiso 1 1 calc R . . O3A O 0.52051(12) -0.30926(8) 0.79252(11) 0.0277(3) Uani 1 1 d . . . C10 C 0.76879(16) -0.08578(12) 0.83533(15) 0.0197(4) Uani 1 1 d . . . H10 H 0.8356 -0.0618 0.7962 0.024 Uiso 1 1 calc R . . C11 C 0.57650(17) -0.15969(13) 0.95218(16) 0.0224(4) Uani 1 1 d . . . H11 H 0.5115 -0.1853 0.9927 0.027 Uiso 1 1 calc R . . C12 C 0.82969(17) 0.08043(13) 0.98640(15) 0.0205(4) Uani 1 1 d . . . C13 C 0.59417(17) -0.21604(12) 0.84675(16) 0.0203(4) Uani 1 1 d . . . C15 C 0.69019(17) -0.17909(12) 0.78885(16) 0.0208(4) Uani 1 1 d . . . H15 H 0.7018 -0.2182 0.7171 0.025 Uiso 1 1 calc R . . C19 C 0.42663(18) -0.35445(14) 0.85382(19) 0.0321(5) Uani 1 1 d . . . H19A H 0.4744 -0.3800 0.9386 0.048 Uiso 1 1 calc R . . H19B H 0.3794 -0.4192 0.8054 0.048 Uiso 1 1 calc R . . H19C H 0.3616 -0.2953 0.8596 0.048 Uiso 1 1 calc R . . N1B N 1.04274(14) 0.30703(11) 1.02091(12) 0.0182(3) Uani 1 1 d . . . N2B N 0.94793(15) 0.32025(12) 1.18660(15) 0.0238(4) Uani 1 1 d . . . H1 H 0.9357(18) 0.3536(13) 1.2529(19) 0.027(5) Uiso 1 1 d . . . H2 H 0.9929(19) 0.2421(17) 0.9923(19) 0.043(6) Uiso 1 1 d . . . H3 H 0.895(2) 0.2537(16) 1.151(2) 0.049(6) Uiso 1 1 d . . . C8 C 1.03403(17) 0.36104(12) 1.12700(15) 0.0183(4) Uani 1 1 d . . . C9 C 1.11708(16) 0.45677(12) 1.16731(15) 0.0191(4) Uani 1 1 d . . . H9 H 1.1126 0.4963 1.2413 0.023 Uiso 1 1 calc R . . C14 C 1.20386(16) 0.49339(12) 1.10134(15) 0.0200(4) Uani 1 1 d . . . C16 C 1.20928(16) 0.43389(13) 0.99145(16) 0.0220(4) Uani 1 1 d . . . H16 H 1.2685 0.4578 0.9438 0.026 Uiso 1 1 calc R . . C17 C 1.29306(18) 0.59528(13) 1.14403(17) 0.0277(4) Uani 1 1 d . . . H17A H 1.2798 0.6242 1.2232 0.042 Uiso 1 1 calc R . . H17B H 1.2703 0.6551 1.0797 0.042 Uiso 1 1 calc R . . H17C H 1.3871 0.5729 1.1569 0.042 Uiso 1 1 calc R . . C18 C 1.12847(16) 0.34197(13) 0.95503(16) 0.0202(4) Uani 1 1 d . . . H18 H 1.1323 0.3013 0.8816 0.024 Uiso 1 1 calc 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 O1A 0.0292(7) 0.0222(7) 0.0221(7) -0.0011(5) 0.0121(6) -0.0068(5) O2A 0.0446(9) 0.0262(7) 0.0257(8) -0.0071(5) 0.0201(7) -0.0114(6) C5 0.0197(9) 0.0172(8) 0.0167(9) 0.0039(7) 0.0052(7) 0.0013(7) C6 0.0237(10) 0.0202(9) 0.0203(10) -0.0004(7) 0.0104(8) 0.0008(7) O3A 0.0280(7) 0.0251(7) 0.0300(8) -0.0044(5) 0.0077(6) -0.0095(5) C10 0.0197(10) 0.0216(9) 0.0189(9) 0.0038(7) 0.0071(8) -0.0006(7) C11 0.0204(9) 0.0243(9) 0.0251(10) 0.0036(7) 0.0106(8) 0.0001(7) C12 0.0255(10) 0.0187(8) 0.0187(10) 0.0031(7) 0.0082(8) 0.0012(7) C13 0.0203(10) 0.0172(9) 0.0210(10) 0.0019(7) 0.0015(8) 0.0001(7) C15 0.0241(10) 0.0205(9) 0.0185(9) -0.0001(7) 0.0071(8) 0.0017(7) C19 0.0299(11) 0.0306(10) 0.0366(12) -0.0012(8) 0.0101(10) -0.0136(8) N1B 0.0209(8) 0.0173(8) 0.0165(8) -0.0004(6) 0.0053(7) 0.0002(6) N2B 0.0310(9) 0.0243(9) 0.0200(9) -0.0041(7) 0.0136(7) -0.0049(7) C8 0.0197(9) 0.0193(9) 0.0152(9) 0.0022(6) 0.0036(8) 0.0034(7) C9 0.0235(10) 0.0181(9) 0.0153(9) -0.0007(7) 0.0044(8) 0.0025(7) C14 0.0196(9) 0.0183(9) 0.0204(10) 0.0018(7) 0.0026(8) 0.0019(7) C16 0.0212(10) 0.0242(9) 0.0222(10) 0.0019(7) 0.0085(8) -0.0013(7) C17 0.0291(11) 0.0286(10) 0.0264(11) -0.0050(8) 0.0093(9) -0.0054(8) C18 0.0229(10) 0.0232(9) 0.0159(9) 0.0009(7) 0.0075(8) 0.0017(7) _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 O1A C12 1.2739(19) . ? O2A C12 1.2559(19) . ? C5 C6 1.386(2) . ? C5 C10 1.397(2) . ? C5 C12 1.504(2) . ? C6 C11 1.388(2) . ? C6 H6 0.9500 . ? O3A C13 1.3743(18) . ? O3A C19 1.425(2) . ? C10 C15 1.377(2) . ? C10 H10 0.9500 . ? C11 C13 1.392(2) . ? C11 H11 0.9500 . ? C13 C15 1.386(2) . ? C15 H15 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? N1B C18 1.351(2) . ? N1B C8 1.355(2) . ? N1B H2 0.93(2) . ? N2B C8 1.329(2) . ? N2B H1 0.868(19) . ? N2B H3 0.97(2) . ? C8 C9 1.411(2) . ? C9 C14 1.367(2) . ? C9 H9 0.9500 . ? C14 C16 1.413(2) . ? C14 C17 1.506(2) . ? C16 C18 1.357(2) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18 0.9500 . ? 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 C6 C5 C10 118.34(14) . . ? C6 C5 C12 120.05(14) . . ? C10 C5 C12 121.58(14) . . ? C5 C6 C11 121.81(15) . . ? C5 C6 H6 119.1 . . ? C11 C6 H6 119.1 . . ? C13 O3A C19 117.23(13) . . ? C15 C10 C5 120.72(15) . . ? C15 C10 H10 119.6 . . ? C5 C10 H10 119.6 . . ? C6 C11 C13 118.58(15) . . ? C6 C11 H11 120.7 . . ? C13 C11 H11 120.7 . . ? O2A C12 O1A 124.01(15) . . ? O2A C12 C5 117.71(15) . . ? O1A C12 C5 118.27(14) . . ? O3A C13 C15 115.45(15) . . ? O3A C13 C11 124.06(15) . . ? C15 C13 C11 120.48(15) . . ? C10 C15 C13 120.04(15) . . ? C10 C15 H15 120.0 . . ? C13 C15 H15 120.0 . . ? O3A C19 H19A 109.5 . . ? O3A C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3A C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 N1B C8 121.85(14) . . ? C18 N1B H2 116.8(12) . . ? C8 N1B H2 121.3(12) . . ? C8 N2B H1 121.5(12) . . ? C8 N2B H3 117.6(12) . . ? H1 N2B H3 120.8(17) . . ? N2B C8 N1B 117.86(15) . . ? N2B C8 C9 124.19(15) . . ? N1B C8 C9 117.95(15) . . ? C14 C9 C8 120.86(15) . . ? C14 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C14 C16 118.96(14) . . ? C9 C14 C17 121.14(14) . . ? C16 C14 C17 119.90(15) . . ? C18 C16 C14 118.92(15) . . ? C18 C16 H16 120.5 . . ? C14 C16 H16 120.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1B C18 C16 121.46(15) . . ? N1B C18 H18 119.3 . . ? C16 C18 H18 119.3 . . ? 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 C10 C5 C6 C11 -1.4(2) . . . . ? C12 C5 C6 C11 176.52(14) . . . . ? C6 C5 C10 C15 2.0(2) . . . . ? C12 C5 C10 C15 -175.93(14) . . . . ? C5 C6 C11 C13 0.1(2) . . . . ? C6 C5 C12 O2A 5.5(2) . . . . ? C10 C5 C12 O2A -176.66(15) . . . . ? C6 C5 C12 O1A -173.49(15) . . . . ? C10 C5 C12 O1A 4.4(2) . . . . ? C19 O3A C13 C15 176.10(14) . . . . ? C19 O3A C13 C11 -4.2(2) . . . . ? C6 C11 C13 O3A -178.97(14) . . . . ? C6 C11 C13 C15 0.7(2) . . . . ? C5 C10 C15 C13 -1.2(2) . . . . ? O3A C13 C15 C10 179.54(13) . . . . ? C11 C13 C15 C10 -0.2(2) . . . . ? C18 N1B C8 N2B -179.34(14) . . . . ? C18 N1B C8 C9 0.5(2) . . . . ? N2B C8 C9 C14 179.63(16) . . . . ? N1B C8 C9 C14 -0.2(2) . . . . ? C8 C9 C14 C16 0.1(2) . . . . ? C8 C9 C14 C17 -179.82(14) . . . . ? C9 C14 C16 C18 -0.2(2) . . . . ? C17 C14 C16 C18 179.68(14) . . . . ? C8 N1B C18 C16 -0.7(2) . . . . ? C14 C16 C18 N1B 0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.263 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 963018' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(XII)-CCDC963019 _audit_creation_method SHELXL-97 _chemical_name_systematic ; benzoic acid + 2-amino-6-methylpyridine ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C7 H5 O2, C6 H9 N2' _chemical_formula_sum 'C13 H14 N2 O2' _chemical_formula_weight 230.26 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 Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 11.888(2) _cell_length_b 12.313(3) _cell_length_c 16.815(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2461.3(9) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4641 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 28.05 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9790 _exptl_absorpt_correction_T_max 0.9840 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4641 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0861 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 28.05 _reflns_number_total 4641 _reflns_number_gt 3081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0539P)^2^+0.5172P] 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 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration unknown _refine_ls_number_reflns 4641 _refine_ls_number_parameters 333 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1051 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1297 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 O1A2 O 0.94721(16) 0.10643(18) 0.45248(15) 0.0327(6) Uani 1 1 d . . . N1B2 N 1.0457(2) -0.0628(2) 0.36974(18) 0.0286(7) Uani 1 1 d . . . O2A2 O 1.11809(17) 0.12866(17) 0.50530(16) 0.0365(6) Uani 1 1 d . . . C3C C 1.0182(2) 0.1591(3) 0.4943(2) 0.0282(8) Uani 1 1 d . . . C9C C 1.0611(3) 0.3253(3) 0.5741(2) 0.0335(9) Uani 1 1 d . . . H9C H 1.1479 0.2996 0.5761 0.040 Uiso 1 1 calc R . . N2B2 N 1.2065(2) -0.0635(2) 0.4471(2) 0.0346(7) Uani 1 1 d . . . H2D H 1.180(3) 0.002(3) 0.468(2) 0.040(10) Uiso 1 1 d . . . C6D C 1.0199(3) -0.1790(3) 0.2599(2) 0.0411(9) Uani 1 1 d . . . H6D H 0.9691 -0.2093 0.2115 0.049 Uiso 1 1 calc R . . C4C C 0.9830(2) 0.2628(3) 0.5339(2) 0.0294(8) Uani 1 1 d . . . C8C C 1.0295(3) 0.4209(3) 0.6121(2) 0.0377(9) Uani 1 1 d . . . H8C H 1.0921 0.4695 0.6420 0.045 Uiso 1 1 calc R . . C5D C 1.1279(3) -0.2220(3) 0.2737(3) 0.0411(9) Uani 1 1 d . . . H5D H 1.1600 -0.2849 0.2352 0.049 Uiso 1 1 calc R . . C3D C 1.1503(2) -0.1034(2) 0.3849(2) 0.0271(8) Uani 1 1 d . . . C8D C 0.8673(3) -0.0468(3) 0.3004(3) 0.0417(10) Uani 1 1 d . . . H8D H 0.8757 0.0400 0.3071 0.063 Uiso 1 1 calc R . . H9D H 0.8121 -0.0780 0.3460 0.063 Uiso 1 1 calc R . . H10D H 0.8324 -0.0648 0.2426 0.063 Uiso 1 1 calc R . . C4D C 1.1924(3) -0.1854(3) 0.3351(2) 0.0339(8) Uani 1 1 d . . . H4D H 1.2751 -0.2190 0.3453 0.041 Uiso 1 1 calc R . . C7D C 0.9805(3) -0.0991(3) 0.3079(2) 0.0315(8) Uani 1 1 d . . . C7C C 0.9200(3) 0.4536(3) 0.6117(3) 0.0546(12) Uani 1 1 d . . . H7C H 0.8955 0.5276 0.6415 0.065 Uiso 1 1 calc R . . C5C C 0.8715(3) 0.2962(4) 0.5344(3) 0.0708(16) Uani 1 1 d . . . H5C H 0.8084 0.2479 0.5047 0.085 Uiso 1 1 calc R . . C6C C 0.8408(4) 0.3913(5) 0.5730(4) 0.096(2) Uani 1 1 d . . . H6C H 0.7538 0.4168 0.5727 0.115 Uiso 1 1 calc R . . O1A1 O 0.02755(16) 0.40288(17) 0.27981(15) 0.0292(5) Uani 1 1 d . . . O2A1 O -0.14312(16) 0.35130(17) 0.24014(17) 0.0422(7) Uani 1 1 d . . . C3A C -0.0385(2) 0.3402(3) 0.2421(2) 0.0265(7) Uani 1 1 d . . . C4A C 0.0098(2) 0.2454(2) 0.1964(2) 0.0259(8) Uani 1 1 d . . . C9A C 0.1259(3) 0.2334(3) 0.1859(2) 0.0297(8) Uani 1 1 d . . . H9A H 0.1830 0.2922 0.2112 0.036 Uiso 1 1 calc R . . C5A C -0.0622(3) 0.1691(3) 0.1638(2) 0.0327(9) Uani 1 1 d . . . H5A H -0.1520 0.1783 0.1712 0.039 Uiso 1 1 calc R . . C8A C 0.1680(3) 0.1451(3) 0.1427(2) 0.0341(8) Uani 1 1 d . . . H8A H 0.2575 0.1369 0.1337 0.041 Uiso 1 1 calc R . . C7A C 0.0959(3) 0.0686(3) 0.1116(3) 0.0428(10) Uani 1 1 d . . . H7A H 0.1289 -0.0004 0.0796 0.051 Uiso 1 1 calc R . . C6A C -0.0204(3) 0.0807(3) 0.1216(3) 0.0455(10) Uani 1 1 d . . . H6A H -0.0775 0.0215 0.0966 0.055 Uiso 1 1 calc R . . N1B1 N -0.0783(2) 0.5653(2) 0.36258(17) 0.0260(6) Uani 1 1 d . . . N2B1 N -0.2381(2) 0.5438(2) 0.28576(19) 0.0324(7) Uani 1 1 d . . . C3B C -0.1854(2) 0.5960(2) 0.3445(2) 0.0280(7) Uani 1 1 d . . . C7B C -0.0170(3) 0.6139(3) 0.4214(2) 0.0305(8) Uani 1 1 d . . . C6B C -0.0627(3) 0.6973(3) 0.4644(2) 0.0376(9) Uani 1 1 d . . . H6B H -0.0149 0.7364 0.5110 0.045 Uiso 1 1 calc R . . C8B C 0.0988(3) 0.5695(3) 0.4352(2) 0.0378(9) Uani 1 1 d . . . H10B H 0.1488 0.5802 0.3821 0.057 Uiso 1 1 calc R . . H9B H 0.0933 0.4841 0.4493 0.057 Uiso 1 1 calc R . . H8B H 0.1378 0.6122 0.4841 0.057 Uiso 1 1 calc R . . C4B C -0.2334(3) 0.6824(2) 0.3877(2) 0.0321(8) Uani 1 1 d . . . H4B H -0.3175 0.7098 0.3740 0.039 Uiso 1 1 calc R . . C5B C -0.1733(3) 0.7314(3) 0.4469(3) 0.0375(8) Uani 1 1 d . . . H5B H -0.2108 0.7968 0.4805 0.045 Uiso 1 1 calc R . . H3B H -0.316(3) 0.558(3) 0.2853(19) 0.031(9) Uiso 1 1 d . . . H2B H -0.205(3) 0.470(3) 0.267(3) 0.062(12) Uiso 1 1 d . . . H3D H 1.275(3) -0.082(3) 0.456(3) 0.056(12) Uiso 1 1 d . . . H1 H 1.019(2) 0.001(2) 0.4003(18) 0.018(8) Uiso 1 1 d . . . H2 H -0.046(3) 0.501(3) 0.325(3) 0.061(12) 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 O1A2 0.0221(11) 0.0357(14) 0.0403(15) -0.0054(12) -0.0045(11) -0.0023(9) N1B2 0.0229(14) 0.0274(15) 0.0354(19) -0.0009(13) -0.0012(13) 0.0007(10) O2A2 0.0187(11) 0.0310(12) 0.0597(18) -0.0030(12) -0.0071(11) 0.0013(9) C3C 0.0231(16) 0.0311(19) 0.030(2) 0.0044(16) -0.0008(15) -0.0054(13) C9C 0.0294(17) 0.029(2) 0.042(3) 0.0019(17) -0.0001(15) -0.0068(13) N2B2 0.0216(15) 0.0378(18) 0.045(2) -0.0046(15) -0.0046(14) 0.0070(12) C6D 0.0381(19) 0.041(2) 0.044(3) -0.0069(18) 0.0001(18) -0.0010(15) C4C 0.0276(17) 0.0298(18) 0.031(2) -0.0032(16) -0.0017(15) 0.0030(13) C8C 0.045(2) 0.0276(19) 0.041(3) -0.0036(18) -0.0030(18) -0.0030(15) C5D 0.038(2) 0.036(2) 0.049(3) -0.0064(18) 0.0085(19) -0.0037(15) C3D 0.0208(16) 0.0262(17) 0.034(2) 0.0028(16) 0.0043(14) -0.0010(12) C8D 0.0283(18) 0.050(2) 0.046(3) -0.0089(18) -0.0148(17) 0.0029(15) C4D 0.0270(17) 0.0296(17) 0.045(2) -0.0020(17) 0.0064(16) 0.0004(13) C7D 0.0297(17) 0.0331(19) 0.032(2) -0.0017(15) -0.0049(15) -0.0053(14) C7C 0.064(3) 0.054(3) 0.046(3) -0.024(2) -0.018(2) 0.016(2) C5C 0.036(2) 0.082(3) 0.094(4) -0.053(3) -0.029(2) 0.022(2) C6C 0.060(3) 0.113(4) 0.114(5) -0.086(4) -0.047(3) 0.049(3) O1A1 0.0186(10) 0.0281(11) 0.0408(15) -0.0027(11) -0.0011(10) -0.0025(8) O2A1 0.0159(11) 0.0351(13) 0.075(2) -0.0139(13) -0.0013(12) -0.0011(9) C3A 0.0214(16) 0.0233(16) 0.035(2) 0.0030(15) -0.0006(15) -0.0023(12) C4A 0.0230(15) 0.0240(17) 0.031(2) 0.0045(15) -0.0014(13) -0.0004(12) C9A 0.0292(17) 0.0289(17) 0.031(2) 0.0022(15) -0.0025(14) 0.0049(13) C5A 0.0310(17) 0.0294(19) 0.038(2) -0.0026(17) 0.0005(15) -0.0029(14) C8A 0.0379(18) 0.0356(19) 0.029(2) 0.0045(16) 0.0015(15) 0.0080(15) C7A 0.048(2) 0.035(2) 0.045(3) -0.0066(19) 0.002(2) 0.0085(16) C6A 0.048(2) 0.038(2) 0.050(3) -0.010(2) -0.003(2) -0.0065(17) N1B1 0.0186(13) 0.0295(14) 0.0297(18) -0.0010(13) -0.0014(11) -0.0011(10) N2B1 0.0194(14) 0.0368(16) 0.041(2) -0.0024(14) -0.0014(13) 0.0033(11) C3B 0.0223(15) 0.0279(17) 0.034(2) 0.0015(16) 0.0015(15) -0.0010(13) C7B 0.0279(16) 0.032(2) 0.031(2) 0.0020(16) -0.0017(15) -0.0028(13) C6B 0.0359(19) 0.040(2) 0.037(2) -0.0088(17) -0.0018(16) 0.0001(15) C8B 0.0279(17) 0.045(2) 0.040(3) -0.0037(18) -0.0087(16) 0.0010(14) C4B 0.0262(16) 0.0332(18) 0.037(2) -0.0012(16) 0.0048(15) 0.0045(13) C5B 0.0376(18) 0.0323(19) 0.043(2) -0.0029(17) 0.0066(18) 0.0038(14) _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 O1A2 C3C 1.275(4) . ? N1B2 C3D 1.364(4) . ? N1B2 C7D 1.373(4) . ? N1B2 H1 0.99(3) . ? O2A2 C3C 1.258(4) . ? C3C C4C 1.500(4) . ? C9C C4C 1.383(5) . ? C9C C8C 1.390(5) . ? C9C H9C 1.0800 . ? N2B2 C3D 1.335(5) . ? N2B2 H2D 0.93(4) . ? N2B2 H3D 0.86(4) . ? C6D C7D 1.357(5) . ? C6D C5D 1.407(5) . ? C6D H6D 1.0800 . ? C4C C5C 1.387(5) . ? C8C C7C 1.363(5) . ? C8C H8C 1.0800 . ? C5D C4D 1.363(5) . ? C5D H5D 1.0800 . ? C3D C4D 1.404(5) . ? C8D C7D 1.496(4) . ? C8D H8D 1.0800 . ? C8D H9D 1.0800 . ? C8D H10D 1.0800 . ? C4D H4D 1.0800 . ? C7C C6C 1.377(6) . ? C7C H7C 1.0800 . ? C5C C6C 1.388(6) . ? C5C H5C 1.0800 . ? C6C H6C 1.0800 . ? O1A1 C3A 1.271(4) . ? O2A1 C3A 1.252(3) . ? C3A C4A 1.510(4) . ? C4A C5A 1.385(4) . ? C4A C9A 1.398(4) . ? C9A C8A 1.400(5) . ? C9A H9A 1.0800 . ? C5A C6A 1.391(5) . ? C5A H5A 1.0800 . ? C8A C7A 1.376(5) . ? C8A H8A 1.0800 . ? C7A C6A 1.401(5) . ? C7A H7A 1.0800 . ? C6A H6A 1.0800 . ? N1B1 C3B 1.362(4) . ? N1B1 C7B 1.366(4) . ? N1B1 H2 1.08(4) . ? N2B1 C3B 1.335(4) . ? N2B1 H3B 0.94(3) . ? N2B1 H2B 1.04(4) . ? C3B C4B 1.409(4) . ? C7B C6B 1.369(5) . ? C7B C8B 1.499(4) . ? C6B C5B 1.412(5) . ? C6B H6B 1.0800 . ? C8B H10B 1.0800 . ? C8B H9B 1.0800 . ? C8B H8B 1.0800 . ? C4B C5B 1.366(5) . ? C4B H4B 1.0800 . ? C5B H5B 1.0800 . ? 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 C3D N1B2 C7D 122.5(3) . . ? C3D N1B2 H1 118.9(16) . . ? C7D N1B2 H1 118.2(16) . . ? O2A2 C3C O1A2 123.7(3) . . ? O2A2 C3C C4C 116.8(3) . . ? O1A2 C3C C4C 119.5(3) . . ? C4C C9C C8C 120.9(3) . . ? C4C C9C H9C 119.5 . . ? C8C C9C H9C 119.5 . . ? C3D N2B2 H2D 117(2) . . ? C3D N2B2 H3D 120(3) . . ? H2D N2B2 H3D 119(3) . . ? C7D C6D C5D 119.3(3) . . ? C7D C6D H6D 120.3 . . ? C5D C6D H6D 120.3 . . ? C9C C4C C5C 118.2(3) . . ? C9C C4C C3C 120.2(3) . . ? C5C C4C C3C 121.5(3) . . ? C7C C8C C9C 120.4(3) . . ? C7C C8C H8C 119.8 . . ? C9C C8C H8C 119.8 . . ? C4D C5D C6D 121.0(3) . . ? C4D C5D H5D 119.5 . . ? C6D C5D H5D 119.5 . . ? N2B2 C3D N1B2 117.9(3) . . ? N2B2 C3D C4D 123.6(3) . . ? N1B2 C3D C4D 118.5(3) . . ? C7D C8D H8D 109.5 . . ? C7D C8D H9D 109.5 . . ? H8D C8D H9D 109.5 . . ? C7D C8D H10D 109.5 . . ? H8D C8D H10D 109.5 . . ? H9D C8D H10D 109.5 . . ? C5D C4D C3D 119.3(3) . . ? C5D C4D H4D 120.4 . . ? C3D C4D H4D 120.4 . . ? C6D C7D N1B2 119.4(3) . . ? C6D C7D C8D 124.9(3) . . ? N1B2 C7D C8D 115.6(3) . . ? C8C C7C C6C 119.4(4) . . ? C8C C7C H7C 120.3 . . ? C6C C7C H7C 120.3 . . ? C4C C5C C6C 120.3(4) . . ? C4C C5C H5C 119.8 . . ? C6C C5C H5C 119.8 . . ? C7C C6C C5C 120.7(4) . . ? C7C C6C H6C 119.7 . . ? C5C C6C H6C 119.7 . . ? O2A1 C3A O1A1 124.1(3) . . ? O2A1 C3A C4A 116.7(3) . . ? O1A1 C3A C4A 119.2(2) . . ? C5A C4A C9A 119.2(3) . . ? C5A C4A C3A 119.4(3) . . ? C9A C4A C3A 121.4(3) . . ? C4A C9A C8A 120.0(3) . . ? C4A C9A H9A 120.0 . . ? C8A C9A H9A 120.0 . . ? C4A C5A C6A 120.8(3) . . ? C4A C5A H5A 119.6 . . ? C6A C5A H5A 119.6 . . ? C7A C8A C9A 120.4(3) . . ? C7A C8A H8A 119.8 . . ? C9A C8A H8A 119.8 . . ? C8A C7A C6A 119.8(3) . . ? C8A C7A H7A 120.1 . . ? C6A C7A H7A 120.1 . . ? C5A C6A C7A 119.8(3) . . ? C5A C6A H6A 120.1 . . ? C7A C6A H6A 120.1 . . ? C3B N1B1 C7B 122.6(3) . . ? C3B N1B1 H2 114(2) . . ? C7B N1B1 H2 124(2) . . ? C3B N2B1 H3B 112(2) . . ? C3B N2B1 H2B 118(2) . . ? H3B N2B1 H2B 122(3) . . ? N2B1 C3B N1B1 118.0(3) . . ? N2B1 C3B C4B 123.7(3) . . ? N1B1 C3B C4B 118.3(3) . . ? N1B1 C7B C6B 119.9(3) . . ? N1B1 C7B C8B 116.2(3) . . ? C6B C7B C8B 123.8(3) . . ? C7B C6B C5B 118.8(3) . . ? C7B C6B H6B 120.6 . . ? C5B C6B H6B 120.6 . . ? C7B C8B H10B 109.5 . . ? C7B C8B H9B 109.5 . . ? H10B C8B H9B 109.5 . . ? C7B C8B H8B 109.5 . . ? H10B C8B H8B 109.5 . . ? H9B C8B H8B 109.5 . . ? C5B C4B C3B 119.8(3) . . ? C5B C4B H4B 120.1 . . ? C3B C4B H4B 120.1 . . ? C4B C5B C6B 120.5(3) . . ? C4B C5B H5B 119.7 . . ? C6B C5B H5B 119.7 . . ? 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 C8C C9C C4C C5C -2.0(6) . . . . ? C8C C9C C4C C3C -179.1(3) . . . . ? O2A2 C3C C4C C9C 5.7(5) . . . . ? O1A2 C3C C4C C9C -174.9(3) . . . . ? O2A2 C3C C4C C5C -171.3(4) . . . . ? O1A2 C3C C4C C5C 8.1(6) . . . . ? C4C C9C C8C C7C 1.5(6) . . . . ? C7D C6D C5D C4D 0.8(6) . . . . ? C7D N1B2 C3D N2B2 -179.2(3) . . . . ? C7D N1B2 C3D C4D 0.0(5) . . . . ? C6D C5D C4D C3D -0.1(5) . . . . ? N2B2 C3D C4D C5D 179.0(3) . . . . ? N1B2 C3D C4D C5D -0.3(5) . . . . ? C5D C6D C7D N1B2 -1.0(5) . . . . ? C5D C6D C7D C8D -179.5(4) . . . . ? C3D N1B2 C7D C6D 0.6(5) . . . . ? C3D N1B2 C7D C8D 179.2(3) . . . . ? C9C C8C C7C C6C -0.4(7) . . . . ? C9C C4C C5C C6C 1.5(8) . . . . ? C3C C4C C5C C6C 178.6(5) . . . . ? C8C C7C C6C C5C -0.1(9) . . . . ? C4C C5C C6C C7C -0.5(10) . . . . ? O2A1 C3A C4A C5A -8.0(5) . . . . ? O1A1 C3A C4A C5A 171.8(3) . . . . ? O2A1 C3A C4A C9A 171.6(3) . . . . ? O1A1 C3A C4A C9A -8.6(5) . . . . ? C5A C4A C9A C8A 0.1(5) . . . . ? C3A C4A C9A C8A -179.5(3) . . . . ? C9A C4A C5A C6A 0.6(6) . . . . ? C3A C4A C5A C6A -179.8(4) . . . . ? C4A C9A C8A C7A -1.2(5) . . . . ? C9A C8A C7A C6A 1.6(6) . . . . ? C4A C5A C6A C7A -0.3(6) . . . . ? C8A C7A C6A C5A -0.8(6) . . . . ? C7B N1B1 C3B N2B1 179.7(3) . . . . ? C7B N1B1 C3B C4B 1.0(5) . . . . ? C3B N1B1 C7B C6B -0.4(5) . . . . ? C3B N1B1 C7B C8B 178.9(3) . . . . ? N1B1 C7B C6B C5B 0.1(5) . . . . ? C8B C7B C6B C5B -179.1(3) . . . . ? N2B1 C3B C4B C5B -179.9(3) . . . . ? N1B1 C3B C4B C5B -1.2(5) . . . . ? C3B C4B C5B C6B 0.9(5) . . . . ? C7B C6B C5B C4B -0.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.835 _diffrn_reflns_theta_full 28.05 _diffrn_measured_fraction_theta_full 0.835 _refine_diff_density_max 0.212 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 963019' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(XIII)-CCDC963020 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-bromobenzoic acid + 2-amino-6-methylpyridine + 2(water) ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C7 H4 Br O2, C6 H9 N2, 2(H2 O)' _chemical_formula_sum 'C13 H17 Br N2 O4' _chemical_formula_weight 345.20 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' 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' Br Br -0.2901 2.4595 '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 17.1239(16) _cell_length_b 4.1317(4) _cell_length_c 22.882(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.762(2) _cell_angle_gamma 90.00 _cell_volume 1503.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8753 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 26.40 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 2.748 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6996 _exptl_absorpt_correction_T_max 0.7707 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Bruker Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8753 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.40 _reflns_number_total 3036 _reflns_number_gt 2400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0512P)^2^+0.1304P] 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 0 _refine_ls_number_reflns 3036 _refine_ls_number_parameters 204 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0820 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.003 _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 Br1 Br 0.859211(16) -0.58912(6) 0.414506(12) 0.03978(11) Uani 1 1 d . . . O2A O 0.43806(11) -0.2024(4) 0.27577(7) 0.0328(4) Uani 1 1 d . . . O1A O 0.49064(12) 0.0276(5) 0.21051(8) 0.0417(5) Uani 1 1 d . . . C11 C 0.74817(15) -0.4462(5) 0.36764(11) 0.0290(5) Uani 1 1 d . . . C13 C 0.60323(16) -0.4171(6) 0.35367(11) 0.0305(5) Uani 1 1 d . . . H13 H 0.5592 -0.4619 0.3683 0.037 Uiso 1 1 calc R . . C12 C 0.68405(17) -0.5189(6) 0.38853(11) 0.0328(6) Uani 1 1 d . . . H12 H 0.6954 -0.6374 0.4264 0.039 Uiso 1 1 calc R . . C7 C 0.49833(16) -0.1352(6) 0.25849(10) 0.0290(5) Uani 1 1 d . . . C8 C 0.58538(15) -0.2493(5) 0.29721(10) 0.0256(5) Uani 1 1 d . . . C9 C 0.65116(16) -0.1808(6) 0.27772(10) 0.0314(5) Uani 1 1 d . . . H9 H 0.6399 -0.0660 0.2395 0.038 Uiso 1 1 calc R . . C10 C 0.73258(16) -0.2752(6) 0.31239(10) 0.0318(5) Uani 1 1 d . . . H10 H 0.7771 -0.2239 0.2986 0.038 Uiso 1 1 calc R . . N2B N 0.27517(15) -0.0049(6) 0.18040(10) 0.0356(5) Uani 1 1 d D . . C2 C 0.20068(16) 0.2931(6) 0.08481(11) 0.0324(5) Uani 1 1 d . . . H2 H 0.1472 0.2386 0.0856 0.039 Uiso 1 1 calc R . . C1 C 0.27507(16) 0.1810(6) 0.13255(10) 0.0277(5) Uani 1 1 d . . . C5 C 0.35669(16) 0.4499(6) 0.08202(11) 0.0295(5) Uani 1 1 d . . . N1B N 0.34968(13) 0.2662(5) 0.12956(9) 0.0276(4) Uani 1 1 d . . . C3 C 0.20678(17) 0.4803(6) 0.03762(11) 0.0340(6) Uani 1 1 d . . . H3 H 0.1571 0.5576 0.0055 0.041 Uiso 1 1 calc R . . C4 C 0.28556(17) 0.5602(6) 0.03598(11) 0.0340(6) Uani 1 1 d . . . H4 H 0.2892 0.6906 0.0029 0.041 Uiso 1 1 calc R . . C6 C 0.44411(17) 0.5133(7) 0.08504(12) 0.0370(6) Uani 1 1 d . . . H6A H 0.4418 0.6357 0.0477 0.056 Uiso 1 1 calc R . . H6B H 0.4730 0.3070 0.0864 0.056 Uiso 1 1 calc R . . H6C H 0.4749 0.6388 0.1230 0.056 Uiso 1 1 calc R . . O1W1 O 0.39590(12) -0.6908(5) 0.33712(8) 0.0340(4) Uani 1 1 d . . . O1W2 O 0.00426(18) 0.2490(13) -0.03510(11) 0.1164(13) Uani 1 1 d . . . H2B H 0.2217(14) -0.085(7) 0.1829(14) 0.055(9) Uiso 1 1 d D . . H2A H 0.3266(15) -0.090(7) 0.2136(12) 0.059(10) Uiso 1 1 d D . . H1 H 0.395(2) 0.183(7) 0.1597(14) 0.050(9) Uiso 1 1 d . . . H3A H 0.410(2) -0.535(9) 0.3205(15) 0.056(10) Uiso 1 1 d . . . H3B H 0.405(2) -0.861(8) 0.3213(14) 0.043(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 Br1 0.02368(16) 0.04552(17) 0.04233(17) 0.00325(12) 0.00314(11) 0.00712(12) O2A 0.0226(9) 0.0388(9) 0.0363(9) 0.0048(7) 0.0101(8) 0.0032(8) O1A 0.0247(10) 0.0625(12) 0.0339(9) 0.0168(9) 0.0063(8) 0.0065(9) C11 0.0231(13) 0.0298(12) 0.0285(12) -0.0033(10) 0.0028(10) 0.0035(10) C13 0.0242(13) 0.0385(13) 0.0277(11) 0.0033(10) 0.0084(10) -0.0012(11) C12 0.0295(15) 0.0385(13) 0.0261(11) 0.0060(10) 0.0053(11) -0.0008(11) C7 0.0226(13) 0.0331(12) 0.0266(11) -0.0019(10) 0.0037(10) 0.0025(10) C8 0.0222(13) 0.0270(11) 0.0250(11) -0.0022(9) 0.0058(9) 0.0005(10) C9 0.0280(14) 0.0416(13) 0.0242(11) 0.0039(10) 0.0091(10) 0.0057(11) C10 0.0270(14) 0.0397(13) 0.0307(12) 0.0007(11) 0.0130(11) 0.0025(11) N2B 0.0227(12) 0.0504(12) 0.0302(11) 0.0049(9) 0.0058(9) -0.0023(10) C2 0.0207(13) 0.0404(13) 0.0331(12) -0.0057(11) 0.0065(10) 0.0018(11) C1 0.0224(13) 0.0315(11) 0.0264(11) -0.0056(9) 0.0056(10) 0.0001(10) C5 0.0288(14) 0.0306(12) 0.0266(11) -0.0041(10) 0.0076(10) -0.0007(10) N1B 0.0195(11) 0.0337(10) 0.0252(10) -0.0013(9) 0.0031(8) 0.0018(9) C3 0.0260(14) 0.0404(13) 0.0270(12) -0.0026(10) -0.0003(10) 0.0073(11) C4 0.0339(15) 0.0372(13) 0.0275(12) 0.0022(11) 0.0073(11) 0.0013(12) C6 0.0298(15) 0.0439(14) 0.0371(13) 0.0040(11) 0.0120(12) -0.0018(12) O1W1 0.0297(11) 0.0411(11) 0.0339(9) -0.0002(9) 0.0148(8) 0.0006(9) O1W2 0.0483(18) 0.239(4) 0.0473(14) -0.012(2) 0.0001(12) -0.002(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 Br1 C11 1.898(2) . ? O2A C7 1.265(3) . ? O1A C7 1.252(3) . ? C11 C12 1.383(3) . ? C11 C10 1.385(3) . ? C13 C12 1.382(4) . ? C13 C8 1.397(3) . ? C13 H13 0.9500 . ? C12 H12 0.9500 . ? C7 C8 1.500(3) . ? C8 C9 1.386(3) . ? C9 C10 1.380(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? N2B C1 1.337(3) . ? N2B H2B 0.996(18) . ? N2B H2A 0.990(18) . ? C2 C3 1.363(4) . ? C2 C1 1.414(3) . ? C2 H2 0.9500 . ? C1 N1B 1.351(3) . ? C5 C4 1.360(4) . ? C5 N1B 1.368(3) . ? C5 C6 1.496(4) . ? N1B H1 0.90(3) . ? C3 C4 1.403(4) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? O1W1 H3A 0.83(4) . ? O1W1 H3B 0.83(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 C12 C11 C10 121.1(2) . . ? C12 C11 Br1 119.64(18) . . ? C10 C11 Br1 119.21(18) . . ? C12 C13 C8 120.9(2) . . ? C12 C13 H13 119.5 . . ? C8 C13 H13 119.5 . . ? C13 C12 C11 119.2(2) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? O1A C7 O2A 124.0(2) . . ? O1A C7 C8 116.4(2) . . ? O2A C7 C8 119.6(2) . . ? C9 C8 C13 118.3(2) . . ? C9 C8 C7 119.6(2) . . ? C13 C8 C7 122.1(2) . . ? C10 C9 C8 121.7(2) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C9 C10 C11 118.7(2) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C1 N2B H2B 121.1(18) . . ? C1 N2B H2A 124.3(19) . . ? H2B N2B H2A 114(3) . . ? C3 C2 C1 119.1(2) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? N2B C1 N1B 118.5(2) . . ? N2B C1 C2 123.2(2) . . ? N1B C1 C2 118.3(2) . . ? C4 C5 N1B 119.0(2) . . ? C4 C5 C6 124.8(2) . . ? N1B C5 C6 116.2(2) . . ? C1 N1B C5 123.2(2) . . ? C1 N1B H1 116(2) . . ? C5 N1B H1 121.0(19) . . ? C2 C3 C4 120.8(2) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.6(2) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? H3A O1W1 H3B 109(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 C8 C13 C12 C11 1.5(4) . . . . ? C10 C11 C12 C13 -0.4(4) . . . . ? Br1 C11 C12 C13 -179.22(18) . . . . ? C12 C13 C8 C9 -1.5(3) . . . . ? C12 C13 C8 C7 -179.9(2) . . . . ? O1A C7 C8 C9 -2.1(3) . . . . ? O2A C7 C8 C9 178.8(2) . . . . ? O1A C7 C8 C13 176.3(2) . . . . ? O2A C7 C8 C13 -2.8(3) . . . . ? C13 C8 C9 C10 0.3(4) . . . . ? C7 C8 C9 C10 178.7(2) . . . . ? C8 C9 C10 C11 0.8(4) . . . . ? C12 C11 C10 C9 -0.8(4) . . . . ? Br1 C11 C10 C9 178.09(18) . . . . ? C3 C2 C1 N2B -179.7(2) . . . . ? C3 C2 C1 N1B 0.3(3) . . . . ? N2B C1 N1B C5 178.7(2) . . . . ? C2 C1 N1B C5 -1.3(3) . . . . ? C4 C5 N1B C1 1.6(3) . . . . ? C6 C5 N1B C1 -178.2(2) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? N1B C5 C4 C3 -0.9(3) . . . . ? C6 C5 C4 C3 178.9(2) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.591 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.064 _database_code_depnum_ccdc_archive 'CCDC 963020' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_data(XIV)-CCDC963021 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-bromobenzoic acid + 2-amino-4-methylpyridine ; _chemical_name_common none _chemical_melting_point none _chemical_formula_moiety 'C7 H4 Br O2, C6 H9 N2' _chemical_formula_sum 'C13 H13 Br N2 O2' _chemical_formula_weight 309.16 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' Br Br -0.2901 2.4595 '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 9.5786(19) _cell_length_b 11.539(2) _cell_length_c 11.311(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.45(3) _cell_angle_gamma 90.00 _cell_volume 1229.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6862 _cell_measurement_theta_min 4.07 _cell_measurement_theta_max 27.86 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 3.339 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6343 _exptl_absorpt_correction_T_max 0.6901 _exptl_absorpt_process_details DENZO-SMN _exptl_special_details ; none ; _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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.2\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6862 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 27.86 _reflns_number_total 2789 _reflns_number_gt 2326 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0275P)^2^+0.1668P] 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 0 _refine_ls_number_reflns 2789 _refine_ls_number_parameters 176 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0557 _refine_ls_wR_factor_gt 0.0526 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.055 _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 Br1 Br 0.544081(18) 0.648741(15) 0.202285(15) 0.01739(7) Uani 1 1 d . . . O1A O 0.09261(13) 1.11360(11) 0.07387(10) 0.0153(3) Uani 1 1 d . . . N1B N -0.04656(14) 1.30212(14) -0.02326(12) 0.0119(3) Uani 1 1 d . . . C5 C 0.42812(17) 0.77660(15) 0.14104(15) 0.0131(4) Uani 1 1 d . . . O2A O 0.18905(13) 1.10955(12) -0.09159(10) 0.0201(3) Uani 1 1 d . . . C7 C -0.03449(18) 1.35504(15) -0.12815(15) 0.0125(4) Uani 1 1 d . . . C9 C 0.25933(17) 0.96469(15) 0.05436(14) 0.0118(3) Uani 1 1 d . . . C10 C 0.24754(18) 0.91369(16) 0.16367(15) 0.0140(4) Uani 1 1 d . . . H10 H 0.1812 0.9436 0.2088 0.017 Uiso 1 1 calc R . . C11 C -0.13540(19) 1.34313(15) 0.04780(15) 0.0146(4) Uani 1 1 d . . . H11 H -0.1415 1.3038 0.1205 0.018 Uiso 1 1 calc R . . C12 C -0.20676(18) 1.49720(16) -0.09139(15) 0.0141(4) Uani 1 1 d . . . C13 C 0.17338(17) 1.07020(15) 0.00807(14) 0.0122(4) Uani 1 1 d . . . C14 C 0.33153(18) 0.81971(16) 0.20745(15) 0.0150(4) Uani 1 1 d . . . H14 H 0.3229 0.7853 0.2821 0.018 Uiso 1 1 calc R . . C16 C -0.11735(18) 1.45437(16) -0.16288(15) 0.0148(4) Uani 1 1 d . . . H16 H -0.1113 1.4920 -0.2365 0.018 Uiso 1 1 calc R . . C18 C -0.21561(17) 1.43901(16) 0.01713(15) 0.0155(4) Uani 1 1 d . . . H18 H -0.2771 1.4668 0.0679 0.019 Uiso 1 1 calc R . . N2B N 0.05501(16) 1.30900(15) -0.19304(13) 0.0172(3) Uani 1 1 d D . . C2 C 0.35653(18) 0.91859(15) -0.01158(15) 0.0144(4) Uani 1 1 d . . . H2 H 0.3642 0.9517 -0.0871 0.017 Uiso 1 1 calc R . . C3 C 0.44166(18) 0.82549(16) 0.03164(16) 0.0162(4) Uani 1 1 d . . . H3 H 0.5085 0.7954 -0.0130 0.019 Uiso 1 1 calc R . . C1 C -0.29296(19) 1.60442(17) -0.12644(17) 0.0198(4) Uani 1 1 d . . . H1A H -0.2523 1.6693 -0.0757 0.030 Uiso 1 1 calc R . . H1B H -0.3910 1.5913 -0.1157 0.030 Uiso 1 1 calc R . . H1C H -0.2920 1.6228 -0.2109 0.030 Uiso 1 1 calc R . . H4 H 0.105(2) 1.2405(16) -0.1629(17) 0.031(6) Uiso 1 1 d D . . H6 H 0.004(2) 1.236(2) 0.0042(18) 0.023(5) Uiso 1 1 d . . . H1 H 0.066(2) 1.3489(18) -0.2661(17) 0.036(7) 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 Br1 0.01623(11) 0.01348(11) 0.02135(11) 0.00034(7) 0.00041(8) 0.00425(7) O1A 0.0193(6) 0.0138(7) 0.0132(6) -0.0015(5) 0.0040(5) 0.0048(6) N1B 0.0139(7) 0.0100(8) 0.0114(7) 0.0004(6) 0.0014(6) 0.0005(6) C5 0.0121(8) 0.0086(9) 0.0171(8) -0.0027(7) -0.0011(7) -0.0007(7) O2A 0.0283(7) 0.0190(7) 0.0146(6) 0.0047(5) 0.0081(6) 0.0071(6) C7 0.0144(8) 0.0105(9) 0.0115(8) -0.0001(7) -0.0006(7) -0.0025(7) C9 0.0132(8) 0.0092(9) 0.0123(8) -0.0024(7) 0.0002(7) -0.0030(7) C10 0.0135(8) 0.0153(10) 0.0130(8) -0.0031(7) 0.0022(7) 0.0007(7) C11 0.0155(9) 0.0168(10) 0.0117(8) -0.0008(7) 0.0027(7) -0.0031(7) C12 0.0125(8) 0.0111(9) 0.0168(8) -0.0003(7) -0.0026(7) -0.0018(7) C13 0.0137(8) 0.0101(9) 0.0123(8) -0.0030(7) 0.0014(7) -0.0013(7) C14 0.0174(9) 0.0147(9) 0.0125(8) 0.0004(7) 0.0017(7) -0.0014(8) C16 0.0158(8) 0.0139(10) 0.0142(8) 0.0023(7) 0.0012(7) -0.0031(8) C18 0.0137(8) 0.0169(10) 0.0162(8) -0.0018(8) 0.0034(7) 0.0017(8) N2B 0.0231(8) 0.0168(9) 0.0135(7) 0.0040(7) 0.0077(7) 0.0052(7) C2 0.0166(9) 0.0119(10) 0.0149(8) -0.0008(7) 0.0033(7) -0.0011(7) C3 0.0143(8) 0.0168(10) 0.0185(9) -0.0026(7) 0.0058(8) 0.0010(7) C1 0.0193(9) 0.0148(10) 0.0250(10) 0.0014(8) 0.0032(8) 0.0025(8) _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 Br1 C5 1.9003(17) . ? O1A C13 1.270(2) . ? N1B C11 1.357(2) . ? N1B C7 1.358(2) . ? N1B H6 0.92(2) . ? C5 C14 1.386(2) . ? C5 C3 1.387(2) . ? O2A C13 1.249(2) . ? C7 N2B 1.336(2) . ? C7 C16 1.409(2) . ? C9 C10 1.392(2) . ? C9 C2 1.399(2) . ? C9 C13 1.509(2) . ? C10 C14 1.387(3) . ? C10 H10 0.9500 . ? C11 C18 1.356(3) . ? C11 H11 0.9500 . ? C12 C16 1.372(2) . ? C12 C18 1.415(2) . ? C12 C1 1.500(3) . ? C14 H14 0.9500 . ? C16 H16 0.9500 . ? C18 H18 0.9500 . ? N2B H4 0.956(16) . ? N2B H1 0.967(16) . ? C2 C3 1.383(3) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? 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 N1B C7 121.50(16) . . ? C11 N1B H6 115.8(12) . . ? C7 N1B H6 122.7(12) . . ? C14 C5 C3 121.15(17) . . ? C14 C5 Br1 118.99(13) . . ? C3 C5 Br1 119.86(13) . . ? N2B C7 N1B 117.78(16) . . ? N2B C7 C16 123.76(15) . . ? N1B C7 C16 118.46(15) . . ? C10 C9 C2 118.79(16) . . ? C10 C9 C13 121.47(14) . . ? C2 C9 C13 119.71(14) . . ? C14 C10 C9 120.82(15) . . ? C14 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C18 C11 N1B 121.34(16) . . ? C18 C11 H11 119.3 . . ? N1B C11 H11 119.3 . . ? C16 C12 C18 118.83(17) . . ? C16 C12 C1 120.91(16) . . ? C18 C12 C1 120.25(15) . . ? O2A C13 O1A 124.84(17) . . ? O2A C13 C9 117.32(14) . . ? O1A C13 C9 117.83(14) . . ? C5 C14 C10 119.22(15) . . ? C5 C14 H14 120.4 . . ? C10 C14 H14 120.4 . . ? C12 C16 C7 120.60(16) . . ? C12 C16 H16 119.7 . . ? C7 C16 H16 119.7 . . ? C11 C18 C12 119.26(16) . . ? C11 C18 H18 120.4 . . ? C12 C18 H18 120.4 . . ? C7 N2B H4 117.8(12) . . ? C7 N2B H1 117.2(13) . . ? H4 N2B H1 125.0(17) . . ? C3 C2 C9 120.89(16) . . ? C3 C2 H2 119.6 . . ? C9 C2 H2 119.6 . . ? C2 C3 C5 119.11(16) . . ? C2 C3 H3 120.4 . . ? C5 C3 H3 120.4 . . ? C12 C1 H1A 109.5 . . ? C12 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C12 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1B C7 N2B -179.80(16) . . . . ? C11 N1B C7 C16 -0.3(2) . . . . ? C2 C9 C10 C14 0.7(3) . . . . ? C13 C9 C10 C14 -177.28(16) . . . . ? C7 N1B C11 C18 -0.2(3) . . . . ? C10 C9 C13 O2A -179.08(16) . . . . ? C2 C9 C13 O2A 2.9(2) . . . . ? C10 C9 C13 O1A 2.1(2) . . . . ? C2 C9 C13 O1A -175.86(15) . . . . ? C3 C5 C14 C10 -0.3(3) . . . . ? Br1 C5 C14 C10 179.42(13) . . . . ? C9 C10 C14 C5 0.0(3) . . . . ? C18 C12 C16 C7 -0.8(3) . . . . ? C1 C12 C16 C7 178.66(16) . . . . ? N2B C7 C16 C12 -179.73(17) . . . . ? N1B C7 C16 C12 0.8(2) . . . . ? N1B C11 C18 C12 0.2(3) . . . . ? C16 C12 C18 C11 0.3(3) . . . . ? C1 C12 C18 C11 -179.16(16) . . . . ? C10 C9 C2 C3 -1.3(3) . . . . ? C13 C9 C2 C3 176.78(16) . . . . ? C9 C2 C3 C5 1.0(3) . . . . ? C14 C5 C3 C2 -0.3(3) . . . . ? Br1 C5 C3 C2 -179.94(13) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.493 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.144 _database_code_depnum_ccdc_archive 'CCDC 963021'