data_2100436 _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 102.465(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.4304(4) _cell_length_b 9.2896(7) _cell_length_c 7.5943(9) _cell_measurement_reflns_used 1235 _cell_measurement_temperature 293 _cell_measurement_theta_max 53 _cell_measurement_theta_min 6 _cell_volume 511.84(8) _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 0.452 _diffrn_measured_fraction_theta_max 0.410 _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 0.048 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 2733 _diffrn_reflns_theta_full 25.223 _diffrn_reflns_theta_max 26.833 _diffrn_reflns_theta_min 2.807 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.714 _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 0.38 _refine_diff_density_min -0.35 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0349 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 37 _refine_ls_number_reflns 434 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0745 _refine_ls_shift/su_max 0.000042 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 1.99P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1891 _refine_ls_wR_factor_gt 0.1748 _refine_ls_wR_factor_ref 0.1891 _reflns_number_gt 348 _reflns_number_total 451 _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 0.5186(6) 0.3349(5) 0.2671(9) 0.0183(12) Uiso 1.0000 . . N N2 0.3838(5) 0.4116(4) 0.1676(8) 0.0193(11) Uiso 1.0000 . . C C3 0.2380(6) 0.3406(5) 0.0406(10) 0.0216(13) Uiso 1.0000 . . C C4 0.1405(6) 0.4433(5) -0.1046(9) 0.0172(12) Uiso 1.0000 . . O O2 0.1757(5) 0.5747(4) -0.0868(7) 0.0266(11) Uiso 1.0000 . . O O3 0.0294(5) 0.3870(4) -0.2341(8) 0.0331(12) Uiso 1.0000 . . C C1 0.6579(6) 0.4149(5) 0.4052(10) 0.0206(13) Uiso 1.0000 . . N N1 0.8378(5) 0.3392(4) 0.4331(8) 0.0225(12) Uiso 1.0000 . . O O1 0.5283(5) 0.2027(4) 0.2550(7) 0.0279(11) Uiso 1.0000 . . H H2 0.9216 0.3867 0.5157 0.0273 Uiso 1.0000 . . H H1 0.8757 0.3347 0.3286 0.0273 Uiso 1.0000 . . H H3 0.8248 0.2489 0.4730 0.0273 Uiso 1.0000 . . H H4 0.6720 0.5148 0.3601 0.0250 Uiso 1.0000 . . H H5 0.6154 0.4195 0.5205 0.0250 Uiso 1.0000 . . H H6 0.3830 0.5076 0.1801 0.0227 Uiso 1.0000 . . H H7 0.2921 0.2603 -0.0189 0.0255 Uiso 1.0000 . . H H8 0.1461 0.3014 0.1060 0.0255 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 . . . 117.1(4) yes N2 C2 O1 . . . 122.7(4) yes C1 C2 O1 . . . 120.1(4) yes C2 N2 C3 . . . 120.1(4) yes C2 N2 H6 . . . 119.7 no C3 N2 H6 . . . 120.2 no N2 C3 C4 . . . 111.7(4) yes N2 C3 H7 . . . 108.9 no C4 C3 H7 . . . 108.4 no N2 C3 H8 . . . 109.3 no C4 C3 H8 . . . 108.7 no H7 C3 H8 . . . 109.7 no C3 C4 O2 . . . 118.6(5) yes C3 C4 O3 . . . 115.9(4) yes O2 C4 O3 . . . 125.4(5) yes C2 C1 N1 . . . 109.2(4) yes C2 C1 H4 . . . 109.0 no N1 C1 H4 . . . 109.3 no C2 C1 H5 . . . 109.6 no N1 C1 H5 . . . 110.0 no H4 C1 H5 . . . 109.7 no C1 N1 H2 . . . 109.5 no C1 N1 H1 . . . 109.9 no H2 N1 H1 . . . 109.7 no C1 N1 H3 . . . 109.2 no H2 N1 H3 . . . 109.3 no H1 N1 H3 . . . 109.3 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 . . 1.325(7) yes C2 C1 . . 1.501(7) yes C2 O1 . . 1.235(5) yes N2 C3 . . 1.445(7) yes N2 H6 . . 0.898 no C3 C4 . . 1.518(8) yes C3 H7 . . 1.001 no C3 H8 . . 0.996 no C4 O2 . . 1.250(5) yes C4 O3 . . 1.254(7) yes C1 N1 . . 1.484(6) yes C1 H4 . . 1.003 no C1 H5 . . 0.994 no N1 H2 . . 0.898 no N1 H1 . . 0.899 no N1 H3 . . 0.903 no