data_2100435 _publ_contact_author_name 'Stephen A. Moggach' _journal_coeditor_code GP5004 _journal_date_accepted 2005-12-15 _journal_date_recd_electronic 2005-11-14 _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section B' _journal_page_first 310 _journal_page_last 320 _journal_paper_category FA _journal_volume 62 _journal_year 2006 _chemical_formula_moiety 'C4 H8 N2 O3' _chemical_formula_sum 'C4 H8 N2 O3' _chemical_formula_weight 132.12 _chemical_melting_point ? _chemical_name_systematic ? _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary 'Kvick et al., (1979) ' _audit_creation_method CRYSTALS_ver_12.82 _cell_angle_alpha 90 _cell_angle_beta 103.882(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.6428(3) _cell_length_b 9.3800(4) _cell_length_c 7.6505(5) _cell_measurement_reflns_used 1234 _cell_measurement_temperature 293 _cell_measurement_theta_max 52 _cell_measurement_theta_min 5 _cell_volume 532.44(5) _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _diffrn_ambient_temperature 293 _diffrn_measured_fraction_theta_full 0.454 _diffrn_measured_fraction_theta_max 0.400 _diffrn_measurement_device_type 'Bruker APEX II' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 2911 _diffrn_reflns_theta_full 25.014 _diffrn_reflns_theta_max 27.189 _diffrn_reflns_theta_min 2.745 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_meas ? _exptl_crystal_description block _exptl_crystal_F_000 280 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.40 _refine_diff_density_min -0.38 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0501 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 37 _refine_ls_number_reflns 455 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.0932 _refine_ls_R_factor_gt 0.0764 _refine_ls_shift/su_max 0.000031 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 2.28P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1981 _refine_ls_wR_factor_gt 0.1839 _refine_ls_wR_factor_ref 0.1981 _reflns_number_gt 360 _reflns_number_total 471 _reflns_threshold_expression I>2.00u(I) loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_site_type_symbol _atom_site_label _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_disorder_assembly _atom_site_disorder_group C C2 0.5163(6) 0.3329(5) 0.2639(10) 0.0180(12) Uiso 1.0000 . . N N2 0.3837(5) 0.4101(4) 0.1660(9) 0.0206(12) Uiso 1.0000 . . C C3 0.2365(7) 0.3412(5) 0.0389(11) 0.0225(13) Uiso 1.0000 . . C C4 0.1398(6) 0.4440(5) -0.1066(9) 0.0191(13) Uiso 1.0000 . . O O2 0.1754(5) 0.5737(4) -0.0883(8) 0.0278(11) Uiso 1.0000 . . O O3 0.0287(5) 0.3884(4) -0.2360(8) 0.0360(13) Uiso 1.0000 . . C C1 0.6572(7) 0.4119(5) 0.4032(11) 0.0216(14) Uiso 1.0000 . . N N1 0.8326(5) 0.3369(4) 0.4307(9) 0.0217(12) Uiso 1.0000 . . O O1 0.5253(5) 0.2024(4) 0.2519(8) 0.0292(12) Uiso 1.0000 . . H H2 0.9161 0.3841 0.5133 0.0263 Uiso 1.0000 . . H H1 0.8667 0.3330 0.3262 0.0263 Uiso 1.0000 . . H H3 0.8210 0.2476 0.4701 0.0263 Uiso 1.0000 . . H H4 0.6699 0.5110 0.3587 0.0258 Uiso 1.0000 . . H H5 0.6190 0.4161 0.5185 0.0258 Uiso 1.0000 . . H H6 0.3849 0.5054 0.1782 0.0245 Uiso 1.0000 . . H H7 0.2858 0.2603 -0.0198 0.0267 Uiso 1.0000 . . H H8 0.1484 0.3040 0.1052 0.0267 Uiso 1.0000 . . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 C2 C1 . . . 116.7(4) yes N2 C2 O1 . . . 123.5(5) yes C1 C2 O1 . . . 119.8(4) yes C2 N2 C3 . . . 120.1(4) yes C2 N2 H6 . . . 119.9 no C3 N2 H6 . . . 120.0 no N2 C3 C4 . . . 111.7(4) yes N2 C3 H7 . . . 108.9 no C4 C3 H7 . . . 108.7 no N2 C3 H8 . . . 109.0 no C4 C3 H8 . . . 108.9 no H7 C3 H8 . . . 109.6 no C3 C4 O2 . . . 118.7(5) yes C3 C4 O3 . . . 115.6(4) yes O2 C4 O3 . . . 125.7(5) yes C2 C1 N1 . . . 109.5(4) yes C2 C1 H4 . . . 109.0 no N1 C1 H4 . . . 109.3 no C2 C1 H5 . . . 109.5 no N1 C1 H5 . . . 109.9 no H4 C1 H5 . . . 109.7 no C1 N1 H2 . . . 109.4 no C1 N1 H1 . . . 109.8 no H2 N1 H1 . . . 109.6 no C1 N1 H3 . . . 109.3 no H2 N1 H3 . . . 109.4 no H1 N1 H3 . . . 109.4 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C2 N2 . . 1.322(7) yes C2 C1 . . 1.515(8) yes C2 O1 . . 1.231(6) yes N2 C3 . . 1.450(8) yes N2 H6 . . 0.898 no C3 C4 . . 1.524(9) yes C3 H7 . . 1.000 no C3 H8 . . 0.998 no C4 O2 . . 1.247(6) yes C4 O3 . . 1.253(8) yes C1 N1 . . 1.483(6) yes C1 H4 . . 1.003 no C1 H5 . . 0.994 no N1 H2 . . 0.899 no N1 H1 . . 0.899 no N1 H3 . . 0.902 no