# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_pico _database_code_depnum_ccdc_archive 'CCDC 866166' #TrackingRef 'pico_boa.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Picolinamide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H6 N2 O' _chemical_formula_weight 122.13 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 5.3463(2) _cell_length_b 11.3075(5) _cell_length_c 19.9400(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.087(3) _cell_angle_gamma 90.00 _cell_volume 1193.45(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1595 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 20.34 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.828 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_reflns_number 13087 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.79 _reflns_number_total 2287 _reflns_number_gt 1192 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _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^)+(0.0615P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2287 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1098 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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 C1A C 0.3213(4) 0.36213(19) 0.21037(11) 0.0425(5) Uani 1 1 d . . . N1A N 0.1790(4) 0.36954(18) 0.26007(10) 0.0551(5) Uani 1 1 d . . . C2A C 0.5273(4) 0.2900(2) 0.21277(12) 0.0571(7) Uani 1 1 d . . . H2A H 0.6217 0.2872 0.1770 0.069 Uiso 1 1 calc R . . C3A C 0.5910(5) 0.2216(2) 0.26977(14) 0.0675(8) Uani 1 1 d . . . H3A H 0.7305 0.1717 0.2731 0.081 Uiso 1 1 calc R . . C4A C 0.4476(5) 0.2273(2) 0.32151(13) 0.0643(7) Uani 1 1 d . . . H4A H 0.4870 0.1817 0.3604 0.077 Uiso 1 1 calc R . . C5A C 0.2457(5) 0.3018(2) 0.31429(12) 0.0641(7) Uani 1 1 d . . . H5A H 0.1483 0.3057 0.3494 0.077 Uiso 1 1 calc R . . C6A C 0.2454(4) 0.43960(19) 0.14976(11) 0.0432(6) Uani 1 1 d . . . N2A N 0.0275(4) 0.4958(2) 0.14897(11) 0.0545(6) Uani 1 1 d . . . H1 H -0.019(4) 0.552(2) 0.1127(12) 0.061(7) Uiso 1 1 d . . . H2 H -0.056(5) 0.481(2) 0.1833(13) 0.075(9) Uiso 1 1 d . . . O1A O 0.3805(3) 0.44910(15) 0.10517(8) 0.0595(5) Uani 1 1 d . . . C1B C -0.0421(4) 0.7946(2) -0.04339(11) 0.0446(6) Uani 1 1 d . . . N1B N 0.0934(4) 0.81173(18) -0.09322(10) 0.0612(6) Uani 1 1 d . . . C2B C -0.2462(5) 0.8632(2) -0.03447(13) 0.0680(8) Uani 1 1 d . . . H2B H -0.3376 0.8482 0.0010 0.082 Uiso 1 1 calc R . . C3B C -0.3132(5) 0.9545(2) -0.07892(15) 0.0762(9) Uani 1 1 d . . . H3B H -0.4508 1.0024 -0.0739 0.091 Uiso 1 1 calc R . . C4B C -0.1756(5) 0.9736(2) -0.13023(14) 0.0668(8) Uani 1 1 d . . . H4B H -0.2160 1.0349 -0.1610 0.080 Uiso 1 1 calc R . . C5B C 0.0226(5) 0.9006(2) -0.13526(14) 0.0713(8) Uani 1 1 d . . . H5B H 0.1155 0.9138 -0.1706 0.086 Uiso 1 1 calc R . . C6B C 0.0344(4) 0.6954(2) 0.00498(12) 0.0492(6) Uani 1 1 d . . . N2B N 0.2351(4) 0.6327(2) -0.00480(12) 0.0581(6) Uani 1 1 d . . . O1B O -0.0882(3) 0.67628(16) 0.05146(8) 0.0745(6) Uani 1 1 d . . . H3 H 0.312(4) 0.651(2) -0.0391(13) 0.060(8) Uiso 1 1 d . . . H4 H 0.287(6) 0.568(3) 0.0282(17) 0.130(13) 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 C1A 0.0468(13) 0.0409(13) 0.0400(13) 0.0002(11) 0.0073(11) -0.0030(11) N1A 0.0626(12) 0.0620(13) 0.0427(12) 0.0091(11) 0.0142(10) 0.0058(11) C2A 0.0597(16) 0.0583(16) 0.0555(16) 0.0072(13) 0.0154(13) 0.0074(13) C3A 0.0644(17) 0.0696(19) 0.0694(18) 0.0163(15) 0.0120(15) 0.0178(14) C4A 0.0757(18) 0.0645(18) 0.0520(16) 0.0175(14) 0.0062(15) 0.0031(15) C5A 0.0767(18) 0.0706(19) 0.0485(15) 0.0115(14) 0.0206(14) 0.0085(15) C6A 0.0486(13) 0.0399(13) 0.0413(13) -0.0027(11) 0.0067(11) -0.0017(11) N2A 0.0583(14) 0.0597(14) 0.0464(13) 0.0121(11) 0.0109(11) 0.0087(11) O1A 0.0689(11) 0.0650(12) 0.0487(10) 0.0107(9) 0.0228(9) 0.0058(9) C1B 0.0523(14) 0.0406(13) 0.0415(13) -0.0010(11) 0.0086(11) 0.0015(11) N1B 0.0696(14) 0.0568(14) 0.0616(14) 0.0147(12) 0.0243(12) 0.0080(11) C2B 0.0710(17) 0.0708(19) 0.0673(18) 0.0086(16) 0.0275(14) 0.0175(15) C3B 0.0748(18) 0.070(2) 0.087(2) 0.0152(17) 0.0218(17) 0.0224(16) C4B 0.0736(18) 0.0532(17) 0.072(2) 0.0156(14) 0.0047(15) 0.0079(15) C5B 0.084(2) 0.0629(18) 0.0724(19) 0.0206(16) 0.0320(16) 0.0087(16) C6B 0.0582(15) 0.0511(15) 0.0392(13) -0.0010(12) 0.0101(12) 0.0049(13) N2B 0.0653(14) 0.0619(15) 0.0497(14) 0.0072(12) 0.0175(12) 0.0120(12) O1B 0.0964(13) 0.0799(14) 0.0545(11) 0.0178(10) 0.0357(10) 0.0291(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 C1A N1A 1.334(3) . ? C1A C2A 1.366(3) . ? C1A C6A 1.502(3) . ? N1A C5A 1.332(3) . ? C2A C3A 1.377(3) . ? C2A H2A 0.9300 . ? C3A C4A 1.371(3) . ? C3A H3A 0.9300 . ? C4A C5A 1.361(3) . ? C4A H4A 0.9300 . ? C5A H5A 0.9300 . ? C6A O1A 1.227(2) . ? C6A N2A 1.325(3) . ? N2A H1 0.97(2) . ? N2A H2 0.88(2) . ? C1B N1B 1.324(3) . ? C1B C2B 1.370(3) . ? C1B C6B 1.499(3) . ? N1B C5B 1.329(3) . ? C2B C3B 1.375(3) . ? C2B H2B 0.9300 . ? C3B C4B 1.359(3) . ? C3B H3B 0.9300 . ? C4B C5B 1.358(3) . ? C4B H4B 0.9300 . ? C5B H5B 0.9300 . ? C6B O1B 1.227(2) . ? C6B N2B 1.323(3) . ? N2B H3 0.87(2) . ? N2B H4 0.99(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 N1A C1A C2A 123.6(2) . . ? N1A C1A C6A 116.3(2) . . ? C2A C1A C6A 120.1(2) . . ? C5A N1A C1A 116.8(2) . . ? C1A C2A C3A 117.9(2) . . ? C1A C2A H2A 121.0 . . ? C3A C2A H2A 121.0 . . ? C4A C3A C2A 119.7(2) . . ? C4A C3A H3A 120.2 . . ? C2A C3A H3A 120.2 . . ? C5A C4A C3A 118.0(2) . . ? C5A C4A H4A 121.0 . . ? C3A C4A H4A 121.0 . . ? N1A C5A C4A 124.0(2) . . ? N1A C5A H5A 118.0 . . ? C4A C5A H5A 118.0 . . ? O1A C6A N2A 123.8(2) . . ? O1A C6A C1A 121.0(2) . . ? N2A C6A C1A 115.3(2) . . ? C6A N2A H1 117.1(13) . . ? C6A N2A H2 115.8(17) . . ? H1 N2A H2 127(2) . . ? N1B C1B C2B 123.0(2) . . ? N1B C1B C6B 117.6(2) . . ? C2B C1B C6B 119.4(2) . . ? C1B N1B C5B 116.5(2) . . ? C1B C2B C3B 118.8(2) . . ? C1B C2B H2B 120.6 . . ? C3B C2B H2B 120.6 . . ? C4B C3B C2B 119.0(3) . . ? C4B C3B H3B 120.5 . . ? C2B C3B H3B 120.5 . . ? C5B C4B C3B 118.0(3) . . ? C5B C4B H4B 121.0 . . ? C3B C4B H4B 121.0 . . ? N1B C5B C4B 124.7(2) . . ? N1B C5B H5B 117.7 . . ? C4B C5B H5B 117.7 . . ? O1B C6B N2B 123.2(2) . . ? O1B C6B C1B 119.4(2) . . ? N2B C6B C1B 117.4(2) . . ? C6B N2B H3 118.2(16) . . ? C6B N2B H4 116.8(18) . . ? H3 N2B H4 125(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.140 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.038 data_picolinamida _database_code_depnum_ccdc_archive 'CCDC 866167' #TrackingRef 'picolinamida_boa.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; \a - picolinamide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N2 O' _chemical_formula_sum 'C6 H6 N2 O' _chemical_formula_weight 122.13 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 5.1973(3) _cell_length_b 7.0850(4) _cell_length_c 16.4114(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.233(4) _cell_angle_gamma 90.00 _cell_volume 592.74(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2849 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 24.00 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_reflns_number 12204 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.15 _reflns_number_total 1309 _reflns_number_gt 989 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _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^)+(0.0423P)^2^+0.0724P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1309 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 O1 O 0.19732(17) -0.18180(15) -0.04185(7) 0.0693(3) Uani 1 1 d . . . N1 N -0.2858(2) -0.45661(16) -0.16745(7) 0.0548(3) Uani 1 1 d . . . N2 N -0.2412(2) -0.14584(18) -0.06842(8) 0.0540(3) Uani 1 1 d . . . H2A H -0.228(3) -0.033(2) -0.0358(9) 0.065 Uiso 1 1 d . . . H2B H -0.395(3) -0.199(2) -0.0889(9) 0.065 Uiso 1 1 d . . . C1 C -0.0562(2) -0.42569(17) -0.11642(7) 0.0444(3) Uani 1 1 d . . . C2 C 0.1456(3) -0.5546(2) -0.10321(9) 0.0540(4) Uani 1 1 d . . . H2 H 0.305(3) -0.523(2) -0.0665(9) 0.065 Uiso 1 1 d . . . C3 C 0.1092(4) -0.7254(2) -0.14429(10) 0.0659(4) Uani 1 1 d . . . H3 H 0.242(3) -0.810(3) -0.1352(10) 0.079 Uiso 1 1 d . . . C4 C -0.1234(4) -0.7578(2) -0.19800(10) 0.0680(5) Uani 1 1 d . . . H4 H -0.155(3) -0.876(3) -0.2287(11) 0.082 Uiso 1 1 d . . . C5 C -0.3126(3) -0.6212(2) -0.20788(10) 0.0650(4) Uani 1 1 d . . . H5 H -0.482(3) -0.643(2) -0.2444(11) 0.078 Uiso 1 1 d . . . C6 C -0.0241(2) -0.23948(18) -0.07240(8) 0.0475(3) Uani 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 O1 0.0429(5) 0.0689(7) 0.0968(8) -0.0305(6) 0.0155(5) -0.0123(5) N1 0.0509(7) 0.0578(7) 0.0549(7) -0.0089(5) 0.0087(5) -0.0077(5) N2 0.0448(6) 0.0494(7) 0.0666(8) -0.0097(6) 0.0082(5) -0.0037(5) C1 0.0458(7) 0.0464(7) 0.0431(6) -0.0002(5) 0.0136(5) -0.0069(5) C2 0.0542(8) 0.0541(8) 0.0541(8) 0.0012(6) 0.0119(6) -0.0002(6) C3 0.0784(11) 0.0514(9) 0.0744(10) -0.0006(7) 0.0308(9) 0.0060(8) C4 0.0858(11) 0.0567(9) 0.0696(10) -0.0180(8) 0.0352(9) -0.0169(8) C5 0.0642(9) 0.0711(10) 0.0605(9) -0.0193(8) 0.0141(7) -0.0159(8) C6 0.0437(7) 0.0478(7) 0.0523(7) -0.0026(6) 0.0124(6) -0.0076(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.2320(14) . ? N1 C1 1.3356(16) . ? N1 C5 1.3355(19) . ? N2 C6 1.3213(16) . ? N2 H2A 0.957(17) . ? N2 H2B 0.887(16) . ? C1 C2 1.3762(19) . ? C1 C6 1.4977(18) . ? C2 C3 1.380(2) . ? C2 H2 0.949(15) . ? C3 C4 1.369(2) . ? C3 H3 0.904(18) . ? C4 C5 1.367(2) . ? C4 H4 0.977(19) . ? C5 H5 0.976(16) . ? 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 C1 N1 C5 116.67(13) . . ? C6 N2 H2A 118.6(8) . . ? C6 N2 H2B 118.7(10) . . ? H2A N2 H2B 121.8(13) . . ? N1 C1 C2 123.39(12) . . ? N1 C1 C6 116.68(11) . . ? C2 C1 C6 119.93(11) . . ? C1 C2 C3 118.50(14) . . ? C1 C2 H2 119.1(10) . . ? C3 C2 H2 122.4(10) . . ? C4 C3 C2 118.80(15) . . ? C4 C3 H3 123.0(11) . . ? C2 C3 H3 118.2(11) . . ? C5 C4 C3 118.81(15) . . ? C5 C4 H4 120.3(10) . . ? C3 C4 H4 120.9(10) . . ? N1 C5 C4 123.80(15) . . ? N1 C5 H5 115.8(10) . . ? C4 C5 H5 120.3(10) . . ? O1 C6 N2 123.51(12) . . ? O1 C6 C1 119.73(11) . . ? N2 C6 C1 116.75(11) . . ? 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 C5 N1 C1 C2 -1.20(19) . . . . ? C5 N1 C1 C6 178.79(12) . . . . ? N1 C1 C2 C3 -0.4(2) . . . . ? C6 C1 C2 C3 179.58(12) . . . . ? C1 C2 C3 C4 1.6(2) . . . . ? C2 C3 C4 C5 -1.1(2) . . . . ? C1 N1 C5 C4 1.7(2) . . . . ? C3 C4 C5 N1 -0.6(2) . . . . ? N1 C1 C6 O1 -161.65(13) . . . . ? C2 C1 C6 O1 18.34(19) . . . . ? N1 C1 C6 N2 18.70(17) . . . . ? C2 C1 C6 N2 -161.31(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.116 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.036 data_picolow1 _database_code_depnum_ccdc_archive 'CCDC 902045' #TrackingRef 'picolow1_boa.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Picolinamide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N2 O' _chemical_formula_sum 'C6 H6 N2 O' _chemical_formula_weight 122.13 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 5.2831(4) _cell_length_b 11.2901(9) _cell_length_c 19.8654(17) _cell_angle_alpha 90.00 _cell_angle_beta 98.2809(17) _cell_angle_gamma 90.00 _cell_volume 1172.55(16) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2542 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 25.39 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.60 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 APEX CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_reflns_number 8215 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.74 _reflns_number_total 2233 _reflns_number_gt 1749 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _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^)+(0.0468P)^2^+0.1607P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2233 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0876 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 C1A C 0.3200(2) 0.36149(11) 0.21127(7) 0.0235(3) Uani 1 1 d . . . N1A N 0.1779(2) 0.36963(11) 0.26181(6) 0.0305(3) Uani 1 1 d . . . C2A C 0.5304(3) 0.28856(13) 0.21343(7) 0.0307(3) Uani 1 1 d . . . H2A H 0.6244 0.2855 0.1773 0.037 Uiso 1 1 calc R . . C3A C 0.5977(3) 0.21992(14) 0.27107(8) 0.0368(4) Uani 1 1 d . . . H3A H 0.7388 0.1699 0.2743 0.044 Uiso 1 1 calc R . . C4A C 0.4536(3) 0.22655(14) 0.32346(8) 0.0350(4) Uani 1 1 d . . . H4A H 0.4947 0.1811 0.3625 0.042 Uiso 1 1 calc R . . C5A C 0.2472(3) 0.30212(14) 0.31656(7) 0.0351(4) Uani 1 1 d . . . H5A H 0.1505 0.3065 0.3521 0.042 Uiso 1 1 calc R . . C6A C 0.2404(3) 0.43865(12) 0.15004(7) 0.0241(3) Uani 1 1 d . . . N2A N 0.0195(2) 0.49499(11) 0.14954(6) 0.0290(3) Uani 1 1 d . . . H1 H -0.032(3) 0.5481(16) 0.1153(9) 0.046(5) Uiso 1 1 d . . . H2 H -0.073(3) 0.4832(14) 0.1840(8) 0.037(4) Uiso 1 1 d . . . O1A O 0.37668(18) 0.44749(9) 0.10463(5) 0.0321(3) Uani 1 1 d . . . C1B C -0.0499(3) 0.79312(12) -0.04444(7) 0.0261(3) Uani 1 1 d . . . N1B N 0.0901(2) 0.81096(11) -0.09421(6) 0.0337(3) Uani 1 1 d . . . C2B C -0.2589(3) 0.86216(14) -0.03572(8) 0.0362(4) Uani 1 1 d . . . H2B H -0.3537 0.8463 -0.0008 0.043 Uiso 1 1 calc R . . C3B C -0.3242(3) 0.95537(14) -0.08006(8) 0.0410(4) Uani 1 1 d . . . H3B H -0.4625 1.0039 -0.0751 0.049 Uiso 1 1 calc R . . C4B C -0.1815(3) 0.97493(14) -0.13143(8) 0.0369(4) Uani 1 1 d . . . H4B H -0.2211 1.0368 -0.1621 0.044 Uiso 1 1 calc R . . C5B C 0.0217(3) 0.90085(14) -0.13655(8) 0.0389(4) Uani 1 1 d . . . H5B H 0.1172 0.9143 -0.1716 0.047 Uiso 1 1 calc R . . C6B C 0.0248(3) 0.69228(12) 0.00407(7) 0.0269(3) Uani 1 1 d . . . N2B N 0.2297(2) 0.63032(11) -0.00539(7) 0.0312(3) Uani 1 1 d . . . O1B O -0.1027(2) 0.67350(10) 0.05040(5) 0.0397(3) Uani 1 1 d . . . H3 H 0.310(3) 0.6463(15) -0.0400(9) 0.045(5) Uiso 1 1 d . . . H4 H 0.277(3) 0.5675(16) 0.0240(9) 0.044(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 C1A 0.0247(7) 0.0225(7) 0.0235(7) -0.0021(5) 0.0046(6) -0.0037(6) N1A 0.0329(7) 0.0337(7) 0.0265(6) 0.0038(5) 0.0093(5) 0.0029(5) C2A 0.0299(8) 0.0325(8) 0.0311(8) 0.0017(6) 0.0093(6) 0.0016(6) C3A 0.0330(8) 0.0354(8) 0.0421(9) 0.0076(7) 0.0053(7) 0.0087(7) C4A 0.0403(9) 0.0335(8) 0.0306(8) 0.0078(6) 0.0032(7) -0.0001(7) C5A 0.0398(9) 0.0403(9) 0.0271(8) 0.0052(7) 0.0108(7) 0.0014(7) C6A 0.0267(7) 0.0237(7) 0.0224(7) -0.0024(5) 0.0050(6) -0.0033(6) N2A 0.0289(7) 0.0326(7) 0.0262(7) 0.0046(6) 0.0066(5) 0.0042(5) O1A 0.0344(6) 0.0348(6) 0.0291(6) 0.0053(4) 0.0118(4) 0.0040(5) C1B 0.0284(7) 0.0259(7) 0.0244(7) -0.0029(6) 0.0046(6) -0.0016(6) N1B 0.0358(7) 0.0316(7) 0.0361(7) 0.0064(6) 0.0129(6) 0.0043(6) C2B 0.0377(9) 0.0379(8) 0.0357(9) 0.0037(7) 0.0150(7) 0.0060(7) C3B 0.0388(9) 0.0364(9) 0.0491(10) 0.0044(7) 0.0106(8) 0.0120(7) C4B 0.0401(9) 0.0299(8) 0.0403(9) 0.0084(7) 0.0043(7) 0.0024(7) C5B 0.0432(9) 0.0374(9) 0.0393(9) 0.0099(7) 0.0168(7) 0.0019(7) C6B 0.0297(8) 0.0292(7) 0.0219(7) -0.0023(6) 0.0044(6) 0.0007(6) N2B 0.0346(7) 0.0328(7) 0.0274(7) 0.0047(6) 0.0086(6) 0.0069(6) O1B 0.0499(7) 0.0432(6) 0.0295(6) 0.0080(5) 0.0177(5) 0.0137(5) _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 C1A N1A 1.3406(17) . ? C1A C2A 1.3791(19) . ? C1A C6A 1.5060(19) . ? N1A C5A 1.3355(19) . ? C2A C3A 1.386(2) . ? C2A H2A 0.9300 . ? C3A C4A 1.377(2) . ? C3A H3A 0.9300 . ? C4A C5A 1.375(2) . ? C4A H4A 0.9300 . ? C5A H5A 0.9300 . ? C6A O1A 1.2368(15) . ? C6A N2A 1.3277(17) . ? N2A H1 0.918(18) . ? N2A H2 0.908(16) . ? C1B N1B 1.3326(17) . ? C1B C2B 1.383(2) . ? C1B C6B 1.507(2) . ? N1B C5B 1.3342(19) . ? C2B C3B 1.384(2) . ? C2B H2B 0.9300 . ? C3B C4B 1.371(2) . ? C3B H3B 0.9300 . ? C4B C5B 1.376(2) . ? C4B H4B 0.9300 . ? C5B H5B 0.9300 . ? C6B O1B 1.2348(16) . ? C6B N2B 1.3246(18) . ? N2B H3 0.876(18) . ? N2B H4 0.930(18) . ? 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 N1A C1A C2A 123.61(13) . . ? N1A C1A C6A 116.34(11) . . ? C2A C1A C6A 120.05(12) . . ? C5A N1A C1A 116.95(12) . . ? C1A C2A C3A 117.98(14) . . ? C1A C2A H2A 121.0 . . ? C3A C2A H2A 121.0 . . ? C4A C3A C2A 119.35(14) . . ? C4A C3A H3A 120.3 . . ? C2A C3A H3A 120.3 . . ? C5A C4A C3A 118.35(14) . . ? C5A C4A H4A 120.8 . . ? C3A C4A H4A 120.8 . . ? N1A C5A C4A 123.76(14) . . ? N1A C5A H5A 118.1 . . ? C4A C5A H5A 118.1 . . ? O1A C6A N2A 124.01(13) . . ? O1A C6A C1A 120.76(12) . . ? N2A C6A C1A 115.23(12) . . ? C6A N2A H1 119.0(10) . . ? C6A N2A H2 119.6(10) . . ? H1 N2A H2 121.3(14) . . ? N1B C1B C2B 123.12(13) . . ? N1B C1B C6B 117.79(12) . . ? C2B C1B C6B 119.09(12) . . ? C1B N1B C5B 116.99(12) . . ? C1B C2B C3B 118.63(14) . . ? C1B C2B H2B 120.7 . . ? C3B C2B H2B 120.7 . . ? C4B C3B C2B 118.87(14) . . ? C4B C3B H3B 120.6 . . ? C2B C3B H3B 120.6 . . ? C3B C4B C5B 118.40(14) . . ? C3B C4B H4B 120.8 . . ? C5B C4B H4B 120.8 . . ? N1B C5B C4B 123.98(14) . . ? N1B C5B H5B 118.0 . . ? C4B C5B H5B 118.0 . . ? O1B C6B N2B 124.04(14) . . ? O1B C6B C1B 119.04(12) . . ? N2B C6B C1B 116.90(12) . . ? C6B N2B H3 119.9(11) . . ? C6B N2B H4 117.7(10) . . ? H3 N2B H4 122.2(15) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.168 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.038 data_picolow2 _database_code_depnum_ccdc_archive 'CCDC 902046' #TrackingRef 'picolow2_boa.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; \a - picolinamide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H6 N2 O' _chemical_formula_sum 'C6 H6 N2 O' _chemical_formula_weight 122.13 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 5.1578(4) _cell_length_b 7.0249(5) _cell_length_c 16.2192(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.728(5) _cell_angle_gamma 90.00 _cell_volume 577.40(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1039 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 24.68 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 APEX CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_reflns_number 3319 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.74 _reflns_number_total 1083 _reflns_number_gt 848 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _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^)+(0.0461P)^2^+0.1319P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1083 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0985 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 O1 O 0.1999(2) -0.18310(17) -0.04244(8) 0.0368(4) Uani 1 1 d . . . N1 N -0.2883(3) -0.4612(2) -0.16831(8) 0.0296(4) Uani 1 1 d . . . N2 N -0.2430(3) -0.1461(2) -0.06844(9) 0.0290(4) Uani 1 1 d . . . H2A H -0.232(3) -0.036(3) -0.0386(11) 0.035 Uiso 1 1 d . . . H2B H -0.404(4) -0.202(3) -0.0870(11) 0.035 Uiso 1 1 d . . . C1 C -0.0570(3) -0.4301(2) -0.11668(9) 0.0244(4) Uani 1 1 d . . . C2 C 0.1465(3) -0.5605(2) -0.10318(10) 0.0289(4) Uani 1 1 d . . . H2 H 0.309(4) -0.527(3) -0.0639(11) 0.035 Uiso 1 1 d . . . C3 C 0.1098(4) -0.7337(3) -0.14425(11) 0.0348(5) Uani 1 1 d . . . H3 H 0.239(4) -0.824(3) -0.1373(12) 0.042 Uiso 1 1 d . . . C4 C -0.1241(4) -0.7665(3) -0.19860(11) 0.0354(5) Uani 1 1 d . . . H4 H -0.157(4) -0.888(3) -0.2289(12) 0.042 Uiso 1 1 d . . . C5 C -0.3153(4) -0.6276(3) -0.20883(11) 0.0341(4) Uani 1 1 d . . . H5 H -0.485(4) -0.646(3) -0.2456(12) 0.041 Uiso 1 1 d . . . C6 C -0.0244(3) -0.2411(2) -0.07281(10) 0.0261(4) Uani 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 O1 0.0239(6) 0.0371(7) 0.0501(8) -0.0154(6) 0.0086(5) -0.0062(5) N1 0.0280(8) 0.0327(8) 0.0284(7) -0.0042(6) 0.0060(6) -0.0042(6) N2 0.0251(7) 0.0264(8) 0.0355(8) -0.0061(6) 0.0054(6) -0.0020(6) C1 0.0260(8) 0.0268(9) 0.0220(8) 0.0014(7) 0.0083(6) -0.0035(7) C2 0.0298(9) 0.0314(9) 0.0268(9) 0.0019(7) 0.0085(7) -0.0006(7) C3 0.0435(11) 0.0281(10) 0.0367(10) 0.0029(8) 0.0173(9) 0.0038(8) C4 0.0461(11) 0.0313(10) 0.0325(10) -0.0088(8) 0.0172(9) -0.0100(8) C5 0.0343(10) 0.0377(10) 0.0310(10) -0.0087(8) 0.0079(8) -0.0088(8) C6 0.0260(9) 0.0275(9) 0.0254(9) -0.0009(7) 0.0067(7) -0.0037(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 O1 C6 1.2390(18) . ? N1 C5 1.335(2) . ? N1 C1 1.342(2) . ? N2 C6 1.323(2) . ? N2 H2A 0.91(2) . ? N2 H2B 0.917(19) . ? C1 C2 1.380(2) . ? C1 C6 1.501(2) . ? C2 C3 1.383(2) . ? C2 H2 0.983(18) . ? C3 C4 1.375(3) . ? C3 H3 0.91(2) . ? C4 C5 1.375(3) . ? C4 H4 0.98(2) . ? C5 H5 0.971(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 116.66(15) . . ? C6 N2 H2A 119.1(11) . . ? C6 N2 H2B 119.8(11) . . ? H2A N2 H2B 120.2(16) . . ? N1 C1 C2 123.54(15) . . ? N1 C1 C6 116.62(14) . . ? C2 C1 C6 119.84(14) . . ? C1 C2 C3 118.42(16) . . ? C1 C2 H2 118.6(11) . . ? C3 C2 H2 123.0(11) . . ? C4 C3 C2 118.78(17) . . ? C4 C3 H3 119.8(12) . . ? C2 C3 H3 121.4(12) . . ? C3 C4 C5 118.84(17) . . ? C3 C4 H4 121.0(11) . . ? C5 C4 H4 120.1(11) . . ? N1 C5 C4 123.71(17) . . ? N1 C5 H5 114.8(11) . . ? C4 C5 H5 121.5(11) . . ? O1 C6 N2 123.70(15) . . ? O1 C6 C1 119.55(14) . . ? N2 C6 C1 116.75(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 C5 N1 C1 C2 -1.1(2) . . . . ? C5 N1 C1 C6 178.54(14) . . . . ? N1 C1 C2 C3 -0.7(2) . . . . ? C6 C1 C2 C3 179.70(13) . . . . ? C1 C2 C3 C4 1.9(2) . . . . ? C2 C3 C4 C5 -1.4(3) . . . . ? C1 N1 C5 C4 1.7(2) . . . . ? C3 C4 C5 N1 -0.5(3) . . . . ? N1 C1 C6 O1 -161.32(15) . . . . ? C2 C1 C6 O1 18.3(2) . . . . ? N1 C1 C6 N2 19.3(2) . . . . ? C2 C1 C6 N2 -161.12(14) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.170 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.046