Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Konstatin Lyssenko' _publ_contact_author_address ; X-ray Structural Center A.N. Nesmeyanov Institute of Organoelement Compounds Russian Academy of Sciences Vavilov Str., 28 Moscow 119991 RUSSIAN FEDERATION ; _publ_contact_author_email KOSTYA@XRLAB.INEOS.AC.RU _publ_section_title ; NO3-...NO3- and NO3-...pi interactions in the crystal of urea nitrate ; _publ_section_references ; Bruker (2005). APEX2 softwarwe package, Bruker AXS Inc., 5465, East Cheryl Parkway, Madison, WI 5317. Sheldrick G.M. (1998). SHELXTL v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; _publ_section_exptl_refinement ; The hydrogen atoms were found in difference Fourier synthesis and refined in isotropic approximation. ; loop_ _publ_author_name 'Konstatin Lyssenko' 'Mikhail Yu. Antipin' 'Denis G. Golovanov' 'Yulia V. Nelyubina' data_1 _database_code_depnum_ccdc_archive 'CCDC 651076' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C H5 N2 O, N O3' _chemical_formula_sum 'C H5 N3 O4' _chemical_formula_weight 123.08 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.9761(1) _cell_length_b 8.2004(1) _cell_length_c 7.3668(1) _cell_angle_alpha 90.00 _cell_angle_beta 103.414(1) _cell_angle_gamma 90.00 _cell_volume 468.697(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 523 _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.744 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.957 _exptl_absorpt_correction_T_max 0.963 _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 SMART APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33142 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 54.99 _reflns_number_total 5960 _reflns_number_gt 4570 _reflns_threshold_expression I>2/s(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _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^)+(0.0574P)^2^+0.0153P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5960 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0985 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O3 O 0.60046(3) 0.03151(3) 0.35267(4) 0.01300(4) Uani 1 1 d . . . O1 O 0.85055(3) 0.56216(3) 0.60134(4) 0.01300(4) Uani 1 1 d . . . N1 N 0.90038(3) 0.29637(3) 0.65576(4) 0.01296(4) Uani 1 1 d . . . O4 O 0.64690(4) -0.22725(3) 0.39540(4) 0.01543(4) Uani 1 1 d . . . C1 C 0.80300(3) 0.41159(3) 0.55926(4) 0.00950(4) Uani 1 1 d . . . N3 N 0.68716(3) -0.08190(3) 0.44137(4) 0.00999(4) Uani 1 1 d . . . N2 N 0.66542(3) 0.37664(3) 0.42740(4) 0.01252(4) Uani 1 1 d . . . O2 O 0.81248(4) -0.05184(3) 0.57373(4) 0.01729(5) Uani 1 1 d . . . H2NB H 0.6313(12) 0.2638(12) 0.3922(12) 0.027(2) Uiso 1 1 d . . . H1NB H 0.8731(11) 0.1908(11) 0.6260(12) 0.0200(18) Uiso 1 1 d . . . H1O H 0.7815(12) 0.6352(13) 0.5308(12) 0.029(2) Uiso 1 1 d . . . H1NA H 0.9894(12) 0.3273(12) 0.7442(12) 0.031(2) Uiso 1 1 d . . . H2NA H 0.5988(12) 0.4540(11) 0.3613(12) 0.025(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.01418(7) 0.00767(6) 0.01456(8) 0.00144(6) -0.00196(6) 0.00117(5) O1 0.01415(8) 0.00637(6) 0.01619(9) -0.00015(6) -0.00113(6) -0.00122(5) N1 0.01319(8) 0.00773(7) 0.01535(10) 0.00188(6) -0.00200(7) 0.00044(6) O4 0.01829(9) 0.00627(6) 0.01806(10) -0.00057(6) -0.00326(7) -0.00131(6) C1 0.01028(7) 0.00673(7) 0.01059(8) 0.00027(6) 0.00061(6) -0.00029(6) N3 0.01075(7) 0.00664(6) 0.01121(8) 0.00020(5) -0.00023(6) -0.00020(5) N2 0.01284(8) 0.00907(7) 0.01305(9) -0.00045(6) -0.00232(6) -0.00051(6) O2 0.01664(9) 0.01044(8) 0.01888(10) -0.00086(7) -0.00792(7) -0.00042(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 O3 N3 1.2492(3) . ? O1 C1 1.3077(3) . ? O1 H1O 0.894(11) . ? N1 C1 1.3211(4) . ? N1 H1NB 0.907(9) . ? N1 H1NA 0.882(9) . ? O4 N3 1.2602(3) . ? C1 N2 1.3173(4) . ? N3 O2 1.2484(3) . ? N2 H2NB 0.982(10) . ? N2 H2NA 0.896(10) . ? 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 O1 H1O 112.9(6) . . ? C1 N1 H1NB 118.3(6) . . ? C1 N1 H1NA 117.6(6) . . ? H1NB N1 H1NA 124.0(8) . . ? O1 C1 N2 121.77(2) . . ? O1 C1 N1 116.47(2) . . ? N2 C1 N1 121.76(2) . . ? O2 N3 O3 120.49(2) . . ? O2 N3 O4 120.31(3) . . ? O3 N3 O4 119.21(2) . . ? C1 N2 H2NB 122.2(6) . . ? C1 N2 H2NA 122.3(6) . . ? H2NB N2 H2NA 115.5(8) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2NB O3 1_555 0.982(10) 1.934(10) 2.9068(4) 170.2(8) ? O1 H1O O2 1_565 0.894(10) 2.591(11) 3.1819(4) 124.4(8) ? O1 H1O O4 1_565 0.894(10) 1.710(10) 2.6037(4) 179.1(11) ? N1 H1NB O2 1_555 0.907(9) 2.063(9) 2.9688(4) 176.9(8) ? N1 H1NA O2 2_756 0.882(9) 2.072(9) 2.9408(4) 167.9(9) ? N2 H2NA O3 2_655 0.895(9) 2.062(9) 2.8874(4) 152.7(8) ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 54.99 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.523 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.071