#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206888.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2206888 loop_ _publ_author_name 'Nichol, Gary S.' 'Clegg, William' _publ_section_title ; Malonamide: an orthorhombic polymorph ; _journal_coeditor_code BT6746 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3427 _journal_page_last o3429 _journal_paper_doi 10.1107/S1600536805030540 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C3 H6 N2 O2' _chemical_formula_moiety 'C3 H6 N2 O2' _chemical_formula_sum 'C3 H6 N2 O2' _chemical_formula_weight 102.10 _chemical_name_common Malonamide _chemical_name_systematic Malonamide _space_group_IT_number 60 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.3602(9) _cell_length_b 7.5178(8) _cell_length_c 11.791(2) _cell_measurement_reflns_used 6050 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.5 _cell_volume 475.14(12) _computing_cell_refinement 'EvalCCD (Duisenberg et al., 2003)' _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_data_reduction EvalCCD _computing_molecular_graphics ; DIAMOND3 (Brandenburg & Putz, 2004) and MERCURY (Version 1.3; Bruno et al., 2002) ; _computing_publication_material 'Bruker SHELXTL and local programs' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 2001)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0089 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 8872 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 4.67 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_correction_T_min 0.911 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'block cut from large plate' _exptl_crystal_F_000 216 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.305 _refine_diff_density_min -0.196 _refine_ls_extinction_coef 0.077(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 43 _refine_ls_number_reflns 539 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.111 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0306 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.1866P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0807 _refine_ls_wR_factor_ref 0.0829 _reflns_number_gt 490 _reflns_number_total 539 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6746.cif _cod_data_source_block I _cod_database_code 2206888 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' loop_ _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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O 0.06613(15) 0.25831(10) 0.37641(7) 0.0222(3) Uani d . 1 O N -0.2702(2) 0.08531(14) 0.40865(9) 0.0250(3) Uani d . 1 N H1N -0.313(3) 0.1499(19) 0.4686(14) 0.030 Uiso d . 1 H H2N -0.355(3) -0.005(3) 0.3895(13) 0.030 Uiso d . 1 H C1 -0.06739(19) 0.12942(13) 0.35078(8) 0.0161(3) Uani d . 1 C C2 0.0000 0.01335(19) 0.2500 0.0161(4) Uani d S 1 C H2 0.136(3) -0.0629(16) 0.2721(11) 0.019 Uiso d . 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O 0.0269(5) 0.0211(5) 0.0187(5) -0.0057(3) 0.0001(3) -0.0038(3) N 0.0295(6) 0.0226(5) 0.0228(5) -0.0060(4) 0.0109(4) -0.0065(4) C1 0.0200(5) 0.0152(5) 0.0131(5) 0.0013(4) -0.0008(4) 0.0014(3) C2 0.0195(7) 0.0142(7) 0.0144(6) 0.000 0.0012(5) 0.000 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' 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_3 _geom_angle H1N N H2N . . 120.8(15) H1N N C1 . . 119.0(10) H2N N C1 . . 120.1(11) O C1 N . . 122.85(10) O C1 C2 . . 120.12(9) N C1 C2 . . 117.02(9) C1 C2 C1 . 3 109.82(12) C1 C2 H2 . . 108.1(8) C1 C2 H2 3 . 112.0(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O C1 1.2420(13) y N H1N 0.887(16) ? N H2N 0.846(19) ? N C1 1.3257(14) y C1 C2 1.5178(13) y C2 H2 0.963(13) ? 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 N H1N O 4_456 0.887(16) 2.058(17) 2.9282(13) 166.4(13) y N H2N O 8 0.846(19) 2.116(19) 2.9502(14) 168.7(15) y loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O C1 C2 C1 3 -45.99(8) y N C1 C2 C1 3 134.54(10) y loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 7623 2 PubChem 7911