data_2100438 _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 101.214(14) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.2437(8) _cell_length_b 9.2083(13) _cell_length_c 7.5328(17) _cell_measurement_reflns_used 1070 _cell_measurement_temperature 293 _cell_measurement_theta_max 52 _cell_measurement_theta_min 6 _cell_volume 492.86(14) _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 0.458 _diffrn_measured_fraction_theta_max 0.401 _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 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 2669 _diffrn_reflns_theta_full 25.262 _diffrn_reflns_theta_max 27.164 _diffrn_reflns_theta_min 2.867 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.780 _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 0.35 _refine_diff_density_min -0.33 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0294 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 37 _refine_ls_number_reflns 422 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0719 _refine_ls_shift/su_max 0.000038 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 2.23P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1874 _refine_ls_wR_factor_gt 0.1692 _refine_ls_wR_factor_ref 0.1874 _reflns_number_gt 318 _reflns_number_total 437 _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 0.5214(6) 0.3376(5) 0.2692(10) 0.0177(13) Uiso 1.0000 . . N N2 0.3849(6) 0.4133(4) 0.1709(9) 0.0181(12) Uiso 1.0000 . . C C3 0.2395(7) 0.3405(5) 0.0407(11) 0.0195(13) Uiso 1.0000 . . C C4 0.1426(6) 0.4434(5) -0.1027(10) 0.0183(13) Uiso 1.0000 . . O O2 0.1782(5) 0.5760(4) -0.0852(8) 0.0252(11) Uiso 1.0000 . . O O3 0.0300(5) 0.3862(4) -0.2332(8) 0.0301(12) Uiso 1.0000 . . C C1 0.6607(7) 0.4177(5) 0.4085(11) 0.0198(14) Uiso 1.0000 . . N N1 0.8432(6) 0.3422(5) 0.4362(9) 0.0203(12) Uiso 1.0000 . . O O1 0.5317(5) 0.2038(4) 0.2573(8) 0.0262(12) Uiso 1.0000 . . H H2 0.9270 0.3901 0.5197 0.0244 Uiso 1.0000 . . H H1 0.8846 0.3395 0.3310 0.0244 Uiso 1.0000 . . H H3 0.8294 0.2510 0.4746 0.0244 Uiso 1.0000 . . H H4 0.6758 0.5190 0.3657 0.0237 Uiso 1.0000 . . H H5 0.6145 0.4207 0.5252 0.0237 Uiso 1.0000 . . H H6 0.3814 0.5103 0.1842 0.0217 Uiso 1.0000 . . H H7 0.2985 0.2604 -0.0187 0.0235 Uiso 1.0000 . . H H8 0.1440 0.2988 0.1059 0.0235 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 . . . 117.6(4) yes N2 C2 O1 . . . 122.4(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 . . . 108.9 no N2 C3 H8 . . . 108.9 no C4 C3 H8 . . . 108.9 no H7 C3 H8 . . . 109.5 no C3 C4 O2 . . . 118.8(5) yes C3 C4 O3 . . . 115.9(4) yes O2 C4 O3 . . . 125.3(5) yes C2 C1 N1 . . . 109.3(4) yes C2 C1 H4 . . . 109.5 no N1 C1 H4 . . . 109.5 no C2 C1 H5 . . . 109.5 no N1 C1 H5 . . . 109.5 no H4 C1 H5 . . . 109.5 no C1 N1 H2 . . . 109.5 no C1 N1 H1 . . . 109.5 no H2 N1 H1 . . . 109.5 no C1 N1 H3 . . . 109.5 no H2 N1 H3 . . . 109.5 no H1 N1 H3 . . . 109.5 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 . . 1.314(7) yes C2 C1 . . 1.501(8) yes C2 O1 . . 1.239(6) yes N2 C3 . . 1.456(8) yes N2 H6 . . 0.900 no C3 C4 . . 1.504(9) yes C3 H7 . . 1.000 no C3 H8 . . 1.000 no C4 O2 . . 1.250(6) yes C4 O3 . . 1.264(8) yes C1 N1 . . 1.472(6) yes C1 H4 . . 1.000 no C1 H5 . . 1.000 no N1 H2 . . 0.900 no N1 H1 . . 0.900 no N1 H3 . . 0.900 no