# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry, 1999 # CCDC Number: 182/1306 data_global _publ_requested_journal ' ChemComm' _publ_contact_author ; Veneta Videnova-Adrabiska Institute of Inorganic Chemistry Wrocaw University of Technology 23 Smoluchowskiego 23 50 370 Wrocw, Poland ; _publ_contact_author_email ' veneta@ichn.ch.chem.wroc.pl' _publ_section_title ; Urea-picoline-N-oxide cocrystal. An unusual channel inclusion compound ; _publ_section_references ; Molecular Structure Corporation, (1985). TEXSAN, TEXRAY Structure Analysis Package; MSC, 3200A Research Forest Drive, The Woodlands, TX 77381, USA. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Johnson, C. K. (1976). ORTEP II. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Gilmore, C. J. (1984). J. Appl. Cryst. 17, 42?46. Cromer, D.T. & Waber, J.T. (1974). International Tables for X-ray Crystallography; vol. IV, The Kynoch Press, Birmingham, England. Beurkens, P.T. (1984). DIRDIF, An automatic procedure for phase extension and refinement of difference structure factors; Tech. Rep. 1984/1. Univ. of Nijmegen, The Netherlands. Motherwell, W. D. S. & Clegg, W. (1978). PLUTO. Program for Plotting Molecular and Crystal Structures. Univ. of Cambridge, England. Ibers, J.A., & Hamilton, W.C., Acta Crystallogr., 1969, 17, 781. ; data_1 _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'MITHRIL DIRDIF' _computing_structure_refinement 'TEXSAN' _computing_molecular_graphics 'ORTEP PLUTO' _computing_publication_material 'PLUTO' _chemical_name_common 'urea:picoline-N-oxide' _chemical_formula_sum 'C8 H15 N5 O3 ' _chemical_formula_weight 229.24 _chemical_melting_point 146-148 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P mc21' _symmetry_Int_Tables_number 26 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, z' '-x, -y, 1/2+z' 'x, -y, 1/2+z' _cell_length_a 7.09(3) _cell_length_b 10.065(3) _cell_length_c 16.267(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1162.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 297 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.15 _cell_measurement_theta_max 23.55 _exptl_crystal_description 'prism' _exptl_crystal_colour 'transparent' _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.300 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method ? _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min none _exptl_absorpt_correction_T_max none _exptl_special_details ; \q scan width 0.70 +0.35tan\q%, \q scan rate 8.2\% per min. ; _diffrn_ambient_temperature 297 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method scanning _diffrn_standards_number 3 _diffrn_standards_interval_time '50 min' _diffrn_standards_decay_% 0 _diffrn_reflns_number 3055 _reflns_number_total 1649 _diffrn_reflns_theta_max 27.95 _diffrn_reflns_av_R_equivalents 0.017 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _reflns_number_observed 1139 _reflns_observed_criterion '> 2.0 sigma(I)' _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'H17 H18 H19 H27 H28 H29 idealised' _refine_ls_extinction_method TEXSAN _refine_ls_extinction_coef '0.69788 E-6' _refine_ls_extinction_expression 'Ibers, J.A., & Hamilton, W.C' _refine_ls_number_reflns 1139 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.043 _refine_ls_wR_factor_ref 0.048 _refine_ls_goodness_of_fit_ref 1.28 _refine_ls_weighting_scheme 'w = 4^Fo^2^/s^2^(Fo^2^)' _refine_ls_shift/su_max 0.03 _refine_diff_density_max 0.16 _refine_diff_density_min -0.20 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O11 O 0.5000 0.9865(7) 0.5500 0.127 Uani 1 d . . N11 N 0.5000 0.9405(5) 0.6250 0.076(4) Uani 1 d . . C12 C 0.5000 0.8089(6) 0.6411(5) 0.084 Uani 1 d . . C13 C 0.5000 0.7625(5) 0.7206(6) 0.080(2) Uani 1 d . . C14 C 0.5000 0.8471(6) 0.7858(5) 0.075(1) Uani 1 d . . C15 C 0.5000 0.9809(6) 0.7662(5) 0.080(2) Uani 1 d . . C16 C 0.5000 1.0230(5) 0.6888(5) 0.071(3) Uani 1 d . . C17 C 0.5000 0.798(1) 0.8735(7) 0.135 Uani 1 d . . H12 H 0.5000 0.7474 0.5969 0.1 Uiso 1 d . . H13 H 0.5000 0.6694 0.7302 0.095 Uiso 1 d . . H15 H 0.5000 1.0445 0.8093 0.095 Uiso 1 d . . H16 H 0.5000 1.1160 0.6786 0.0846 Uiso 1 d . . H17 H 0.5000 0.7032 0.8737 0.1608 Uiso 1 d . . H18 H 0.3907 0.8292 0.9009 0.1608 Uiso 1 d . . H19 H 0.6093 0.8292 0.9009 0.1608 Uiso 1 d . . O21 O 1.0000 0.9533(3) 0.5864(3) 0.067(4) Uani 1 d . . N21 N 1.0000 0.8748(3) 0.6510(3) 0.047(1) Uani 1 d . . C22 C 1.0000 0.7410(4) 0.6407(4) 0.052(2) Uani 1 d . . C23 C 1.0000 0.6592(4) 0.7070(4) 0.052(2) Uani 1 d . . C24 C 1.0000 0.7087(5) 0.7861(4) 0.052(2) Uani 1 d . . C25 C 1.0000 0.8452(5) 0.7942(4) 0.059(8) Uani 1 d . . C26 C 1.0000 0.9260(4) 0.7273(4) 0.052(2) Uani 1 d . . C27 C 1.0000 0.6194(7) 0.8598(5) 0.087(8) Uani 1 d . . H22 H 1.0000 0.7044 0.5869 0.0621 Uiso 1 d . . H23 H 1.0000 0.5657 0.6988 0.0633 Uiso 1 d . . H25 H 1.0000 0.8834 0.8476 0.0709 Uiso 1 d . . H26 H 1.0000 1.0196 0.7345 0.0633 Uiso 1 d . . H27 H 1.0000 0.6717 0.9085 0.1038 Uiso 1 d . . H28 H 0.8907 0.5649 0.8589 0.1038 Uiso 1 d . . H29 H 1.1093 0.5649 0.8589 0.1038 Uiso 1 d . . O10 O 1.0000 0.7464(4) 0.3296(3) 0.068(6) Uani 1 d . . N10 N 0.8379(5) O.8521(4) 0.4283(4) 0.064(8) Uani 1 d . . C10 C 1.0000 0.8126(5) 0.3933(4) 0.050(9) Uani 1 d . . H1N10 H 0.73(1) 0.802(6) 0.408(5) 0.167(2) Uiso 1 d . . H2N10 H 0.847(5) 0.887(4) 0.472(3) 0.064(6) Uiso 1 d . . O20 O 1.0000 1.4137(3) 0.5718(3) 0.053(3) Uani 1 d . . N20 N 0.8391(5) 1.2216(3) 0.5695(3) 0.062(2) Uani 1 d . . C20 C 1.0000 1.2897(4) 0.5711(4) 0.047(1) Uani 1 d . . H1N20 H 0.737(6) 1.268(3) 0.567(2) 0.065(6) Uiso 1 d . . H2N20 H 0.841(4) 1.142(3) 0.564(2) 0.036(2) Uiso 1 d . . O30 O 0.5000 0.7048(3) 0.3668(3) 0.050(8) Uani 1 d . . N30 N 0.6611(4) 0.6330(3) 0.2556(3) 0.058(4) Uani 1 d . . C30 C 0.5000 0.6598(4) 0.2957(4) 0.045(8) Uani 1 d . . H1N30 H 0.764(5) 0.659(3) 0.281(2) 0.065(6) Uiso 1 d . . H2N30 H 0.654(5) 0.616(3) 0.202(2) 0.051(5) Uiso 1 d . . O40 O 0.5000 1.3997(3) 0.5884(3) 0.054(6) Uani 1 d . . N40 N 0.6601(4) 1.5358(3) 0.5035(3) 0.054(6) Uani 1 d . . C40 C 0.5000 1.4864(4) 0.5336(4) 0.044(6) Uani 1 d . . H1N40 H 0.754(5) 1.507(4) 0.525(3) 0.077(3) Uiso 1 d . . H2N40 H 0.659(6) 1.591(4) 0.454(3) 0.089(9) Uiso 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 O11 0.157(5) 0.140(5) 0.083(3) 0.010(3) 0.0 0.0 N11 0.068(3) 0.079(3) 0.080(4) -0.006(3) 0.0 0.0 C12 0.087(4) 0.063(3) 0.100(5) -0.033(4) 0.0 0.0 C13 0.065(3) 0.051(3) 0.122(6) -0.001(4) 0.0 0.0 C14 0.050(3) 0.084(4) 0.090(4) 0.006(4) 0.0 0.0 C15 0.078(4) 0.072(4) 0.088(5) -0.023(3) 0.0 0.0 C16 0.075(4) 0.050(3) 0.086(4) -0.005(3) 0.0 0.0 C17 0.099(6) 0.18(1) 0.120(7) 0.055(7) 0.0 0.0 O21 0.092(3) 0.054(2) 0.058(2) 0.008(2) 0.0 0.0 N21 0.051(2) 0.044(2) 0.047(2) -0.002(2) 0.0 0.0 C22 0.065(3) 0.041(2) 0.049(2) -0.009(2) 0.0 0.0 C23 0.060(3) 0.040(2) 0.057(3) -0.002(2) 0.0 0.0 C24 0.051(3) 0.056(3) 0.051(2) 0.003(2) 0.0 0.0 C25 0.069(3) 0.061(3) 0.048(3) -0.013(2) 0.0 0.0 C26 0.054(3) 0.044(2) 0.060(3) -0.012(2) 0.0 0.0 C27 0.111(5) 0.088(4) 0.062(3) 0.015(3) 0.0 0.0 O10 0.052(2) 0.089(3) 0.065(2) -0.022(2) 0.0 0.0 N10 0.057(2) 0.076(2) 0.060(2) -0.013(2) 0.004(2) 0.005(2) C10 0.052(3) 0.048(2) 0.052(3) 0.002(2) 0.0 0.0 O20 0.049(2) 0.043(2) 0.069(2) -0.005(2) 0.0 0.0 N20 0.052(2) 0.043(1) 0.093(2) 0.002(1) 0.003(2) -0.005(2) C20 0.053(3) 0.045(2) 0.043(2) -0.001(2) 0.0 0.0 O30 0.049(2) 0.061(2) 0.042(2) 0.001(2) 0.0 0.0 N30 0.046(2) 0.081(2) 0.049(2) -0.009(1) 0.0 0.0 C30 0.048(2) 0.044(2) 0.044(2) 0.006(2) 0.0 0.0 O40 0.045(2) 0.063(2) 0.057(2) 0.020(2) 0.0 0.0 N40 0.044(2) 0.061(2) 0.059(2) 0.017(1) 0.003(1) -0.001(1) C40 0.049(2) 0.041(2) 0.044(2) -0.001(2) 0.0 0.0 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 O11 N11 1.305(3) . no N11 C12 1.350(8) . no N11 C16 1.329(7) . no C12 C13 1.37(1) . no C12 H12 0.950 . no C13 C14 1.361(9) . no C13 H13 0.950 . no C14 C15 1.384(9) . no C14 C17 1.51(1) . no C15 C16 1.329(9) . no C15 H15 0.950 . no C16 H16 0.950 . no C17 H17 0.950 . no C17 H18 0.950 . no C17 H19 0.950 . no O21 N21 1.316(5) . no N21 C22 1.357(5) . no N21 C26 1.344(6) . no C22 C23 1.357(7) . no C22 H22 0.950 . no C23 C24 1.380(6) . no C23 H23 0.950 . no C24 C25 1.380(7) . no C24 C27 1.499(8) . no C25 C26 1.359(7) . no C25 H25 0.950 . no C26 H26 0.950 . no C27 H27 0.950 . no C27 H28 0.950 . no C27 H29 0.950 . no O10 C10 1.233(5) . no N10 C10 1.343(6) . no N10 H1N10 0.96(7) . no N10 H2N10 0.80(4) . no O20 C20 1.249(5) . no N20 C20 1.332(5) . no N20 H1N20 0.86(4) . no N20 H2N20 0.81(3) . no O30 C30 1.243(5) . no N30 C30 1.343(6) . no N30 H1N30 0.88(4) . no N30 H2N30 0.89(4) . no O40 C40 1.247(5) . no N40 C40 1.334(5) . no N40 H1N40 0.80(4) . no N40 H2N40 0.97(5) . no 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 O11 N11 C12 122.0(5) . . no O11 N11 C16 120.5(6) . . no C12 N11 C16 117.5(5) . . no N11 C12 C13 121.1(5) . . no N11 C12 H12 119.48 . . no C13 C12 H12 119.44 . . no C12 C13 C14 121.4(5) . . no C12 C13 H13 119.30 . . no C14 C13 H13 119.30 . . no C13 C14 C15 115.4(6) . . no C13 C14 C17 122.0(7) . . no C15 C14 C17 122.6(7) . . no C14 C15 C16 122.0(6) . . no C14 C15 H15 119.01 . . no C16 C15 H15 119.02 . . no N11 C16 C15 122.7(5) . . no N11 C16 H16 118.66 . . no C15 C16 H16 118.65 . . no C14 C17 H17 109.46 . . no C14 C17 H18 109.48 . . no C14 C17 H19 109.48 . . no H17 C17 H18 109.46 . . no H17 C17 H19 109.46 . . no H18 C17 H19 109.50 . . no O21 N21 C22 119.9(4) . . no O21 N21 C26 120.5(3) . . no C22 N21 C26 119.6(4) . . no N21 C22 C23 120.3(4) . . no N21 C22 H22 119.87 . . no C23 C22 H22 119.86 . . no C22 C23 C24 121.5(4) . . no C22 C23 H23 119.26 . . no C24 C23 H23 119.26 . . no C23 C24 C25 116.6(4) . . no C23 C24 C27 122.0(4) . . no C25 C24 C27 121.4(5) . . no C24 C25 C26 121.3(4) . . no C24 C25 H25 119.35 . . no C26 C25 H25 119.37 . . no N21 C26 C25 120.7(4) . . no N21 C26 H26 119.66 . . no C25 C26 H26 119.66 . . no C24 C27 H27 109.46 . . no C24 C27 H28 109.48 . . no C24 C27 H29 109.48 . . no H27 C27 H28 109.47 . . no H27 C27 H29 109.47 . . no H28 C27 H29 109.48 . . no C10 N10 H1N10 112(4) . . no C10 N10 H2N10 116(3) . . no H1N10 N10 H2N10 127(5) . . no O10 C10 N10 121.1(3) . . no O10 C10 N10 121.1(3) . . no N10 C10 N10 117.8(5) . . no C20 N20 H1N20 116(2) . . no C20 N20 H2N20 120(2) . . no H1N20 N20 H2N20 123(3) . . no O20 C20 N20 121.0(2) . . no O20 C20 N20 121.0(2) . . no N20 C20 N20 118.0(5) . . no C30 N30 H1N30 115(2) . . no C30 N30 H2N30 118(2) . . no H1N30 N30 H2N30 124(3) . . no O30 C30 N30 121.6(2) . . no O30 C30 N30 121.6(2) . . no N30 C30 N30 116.7(5) . . no C40 N40 H1N40 114(3) . . no C40 N40 H2N40 121(3) . . no H1N40 N40 H2N40 125(4) . . no O40 C40 N40 121.6(2) . . no O40 C40 N40 121.6(2) . . no N40 C40 N40 116.8(5) . . no