#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011913.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_2011913 loop_ _publ_author_name 'Ferguson, George' 'Glidewell, Christopher' _publ_section_title ; N-Propionylhydroxylamine forms a three-dimensional hydrogen-bonded framework structure ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 452 _journal_page_last 454 _journal_paper_doi 10.1107/S0108270101000075 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C3 H7 N O2' _chemical_formula_sum 'C3 H7 N O2' _chemical_formula_weight 89.10 _chemical_name_common 'ethylhydroxamic acid' _chemical_name_systematic ; N-propionylhydroxylamine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 92.35(2) _cell_angle_gamma 90 _cell_formula_units_Z 12 _cell_length_a 12.052(3) _cell_length_b 8.009(3) _cell_length_c 14.354(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 11.23 _cell_measurement_theta_min 9.81 _cell_volume 1384.3(7) _computing_cell_refinement 'SET4 and CELDIM (Nonius, 1992)' _computing_data_collection 'CAD4 (Nonius, 1992)' _computing_data_reduction 'HELENA in PLATON (Spek 2000)' _computing_molecular_graphics 'PLATON (Spek, 2000)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .998 _diffrn_measured_fraction_theta_max .998 _diffrn_measurement_device_type 'Nonius CAD4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .017 _diffrn_reflns_av_sigmaI/netI .0154 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 3374 _diffrn_reflns_theta_full 26.97 _diffrn_reflns_theta_max 26.97 _diffrn_reflns_theta_min 2.84 _diffrn_standards_decay_% negligible _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .107 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 576 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .40 _refine_diff_density_max .186 _refine_diff_density_min -.277 _refine_ls_extinction_coef .026(3) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 170 _refine_ls_number_reflns 3016 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all .0504 _refine_ls_R_factor_gt .0376 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.3743P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1138 _reflns_number_gt 2426 _reflns_number_total 3016 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1449.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2011913 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' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O11 .16302(8) .37086(14) .32034(9) .0536(3) Uani d . 1 . . O O12 .12245(8) .05820(13) .37449(7) .0456(3) Uani d . 1 . . O N1 .04621(8) .18708(15) .38178(8) .0372(3) Uani d . 1 . . N C11 .07007(10) .33463(17) .34863(9) .0348(3) Uani d . 1 . . C C12 -.02402(11) .45828(19) .34589(11) .0433(3) Uani d . 1 . . C C13 .00887(14) .6290(2) .38140(13) .0562(4) Uani d . 1 . . C O21 .15986(7) .57334(15) .04293(7) .0483(3) Uani d . 1 . . O O22 .20525(8) .64442(13) .22256(7) .0427(3) Uani d . 1 . . O N2 .28637(8) .60463(15) .16042(8) .0376(3) Uani d . 1 . . N C21 .25830(10) .57854(17) .07233(9) .0351(3) Uani d . 1 . . C C22 .35365(11) .5567(2) .00888(10) .0462(4) Uani d . 1 . . C C23 .35481(16) .6881(3) -.06606(13) .0671(5) Uani d . 1 . . C O31 .50451(8) .08237(15) .23862(8) .0496(3) Uani d . 1 . . O O32 .45586(9) .31530(15) .36718(8) .0503(3) Uani d . 1 . . O N3 .37691(9) .23735(16) .30936(9) .0423(3) Uani d . 1 . . N C31 .40608(10) .12399(17) .24912(10) .0375(3) Uani d . 1 . . C C32 .31184(12) .0503(2) .19124(12) .0491(4) Uani d . 1 . . C C33 .31564(16) .0997(3) .09140(14) .0723(6) Uani d . 1 . . C H12 .1322 .0128 .4254 .068 Uiso calc R 1 . . H H1 -.0159 .1703 .4077 .045 Uiso calc R 1 . . H H12A -.0831 .4155 .3831 .052 Uiso calc R 1 . . H H12B -.0531 .4685 .2821 .052 Uiso calc R 1 . . H H13A .0432 .6192 .4427 .084 Uiso calc R 1 . . H H13B -.0560 .6982 .3839 .084 Uiso calc R 1 . . H H13C .0604 .6784 .3402 .084 Uiso calc R 1 . . H H22 .1902 .5614 .2530 .064 Uiso calc R 1 . . H H2 .3547 .5971 .1795 .045 Uiso calc R 1 . . H H22A .3486 .4473 -.0200 .055 Uiso calc R 1 . . H H22B .4229 .5615 .0456 .055 Uiso calc R 1 . . H H23A .2864 .6838 -.1027 .101 Uiso calc R 1 . . H H23B .4159 .6681 -.1054 .101 Uiso calc R 1 . . H H23C .3628 .7963 -.0378 .101 Uiso calc R 1 . . H H32 .4750 .4031 .3432 .075 Uiso calc R 1 . . H H3 .3080 .2636 .3130 .051 Uiso calc R 1 . . H H32A .3149 -.0705 .1959 .059 Uiso calc R 1 . . H H32B .2420 .0869 .2157 .059 Uiso calc R 1 . . H H33A .3036 .2179 .0857 .108 Uiso calc R 1 . . H H33B .2588 .0413 .0558 .108 Uiso calc R 1 . . H H33C .3870 .0720 .0683 .108 Uiso calc R 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 O11 .0317(5) .0521(6) .0784(8) .0049(4) .0193(5) .0184(6) O12 .0445(5) .0481(6) .0446(5) .0145(4) .0054(4) .0095(4) N1 .0256(5) .0436(6) .0427(6) .0034(4) .0056(4) .0060(5) C11 .0255(6) .0445(7) .0345(6) .0023(5) .0024(5) .0034(5) C12 .0312(6) .0484(8) .0502(8) .0074(6) .0018(6) .0044(6) C13 .0560(9) .0511(9) .0624(10) .0063(7) .0140(8) -.0039(8) O21 .0266(5) .0720(7) .0463(6) .0015(4) -.0008(4) -.0150(5) O22 .0426(5) .0453(6) .0413(5) .0016(4) .0134(4) .0008(4) N2 .0255(5) .0491(7) .0383(6) .0012(5) .0028(4) -.0006(5) C21 .0262(6) .0381(7) .0411(7) .0012(5) .0030(5) -.0038(5) C22 .0309(6) .0637(10) .0446(8) .0037(6) .0078(6) -.0067(7) C23 .0664(11) .0741(12) .0622(11) -.0079(9) .0219(9) .0051(9) O31 .0274(5) .0599(7) .0614(7) .0068(4) .0002(4) -.0054(5) O32 .0449(6) .0546(7) .0509(6) -.0078(5) -.0063(5) -.0010(5) N3 .0250(5) .0468(7) .0553(7) -.0010(5) .0015(5) -.0017(6) C31 .0259(6) .0384(7) .0482(7) -.0013(5) .0022(5) .0084(6) C32 .0329(7) .0487(8) .0654(10) -.0083(6) -.0001(6) -.0033(7) C33 .0613(11) .0925(15) .0619(11) -.0137(10) -.0109(9) .0024(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 5 0 3 -2 -5 0 -4 -3 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 O12 H12 109.5 C11 N1 O12 119.16(10) C11 N1 H1 120.4 O12 N1 H1 120.4 O11 C11 N1 122.96(12) O11 C11 C12 121.78(13) N1 C11 C12 115.26(11) C11 C12 C13 113.63(12) C11 C12 H12A 108.8 C13 C12 H12A 108.8 C11 C12 H12B 108.8 C13 C12 H12B 108.8 H12A C12 H12B 107.7 C12 C13 H13A 109.5 C12 C13 H13B 109.5 H13A C13 H13B 109.5 C12 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 N2 O22 H22 109.5 C21 N2 O22 119.70(10) C21 N2 H2 120.1 O22 N2 H2 120.1 O21 C21 N2 122.48(12) O21 C21 C22 122.15(12) N2 C21 C22 115.37(11) C21 C22 C23 112.37(14) C21 C22 H22A 109.1 C23 C22 H22A 109.1 C21 C22 H22B 109.1 C23 C22 H22B 109.1 H22A C22 H22B 107.9 C22 C23 H23A 109.5 C22 C23 H23B 109.5 H23A C23 H23B 109.5 C22 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 N3 O32 H32 109.5 C31 N3 O32 120.71(11) C31 N3 H3 119.6 O32 N3 H3 119.6 O31 C31 N3 123.14(13) O31 C31 C32 122.00(14) N3 C31 C32 114.84(12) C33 C32 C31 112.07(13) C33 C32 H32A 109.2 C31 C32 H32A 109.2 C33 C32 H32B 109.2 C31 C32 H32B 109.2 H32A C32 H32B 107.9 C32 C33 H33A 109.5 C32 C33 H33B 109.5 H33A C33 H33B 109.5 C32 C33 H33C 109.5 H33A C33 H33C 109.5 H33B C33 H33C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O11 C11 . 1.2414(15) ? O12 N1 . 1.3887(15) ? O12 H12 . .82 ? N1 C11 . 1.3103(18) ? N1 H1 . .86 ? C11 C12 . 1.5048(18) ? C12 C13 . 1.507(2) ? C12 H12A . .97 ? C12 H12B . .97 ? C13 H13A . .96 ? C13 H13B . .96 ? C13 H13C . .96 ? O21 C21 . 1.2435(15) ? O22 N2 . 1.3872(14) ? O22 H22 . .82 ? N2 C21 . 1.3121(17) ? N2 H2 . .86 ? C21 C22 . 1.5055(18) ? C22 C23 . 1.506(3) ? C22 H22A . .97 ? C22 H22B . .97 ? C23 H23A . .96 ? C23 H23B . .96 ? C23 H23C . .96 ? O31 C31 . 1.2472(16) ? O32 N3 . 1.3854(15) ? O32 H32 . .82 ? N3 C31 . 1.3117(19) ? N3 H3 . .86 ? C31 C32 . 1.501(2) ? C32 C33 . 1.489(3) ? C32 H32A . .97 ? C32 H32B . .97 ? C33 H33A . .96 ? C33 H33B . .96 ? C33 H33C . .96 ? 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 O12 H12 O21 4_566 .82 1.84 2.6589(15) 175 yes N1 H1 O21 2_545 .86 2.05 2.8958(15) 166 yes O22 H22 O11 . .82 1.84 2.6624(16) 177 yes N2 H2 O31 2_655 .86 2.03 2.8609(16) 163 yes O32 H32 O31 2_655 .82 1.88 2.6775(17) 165 yes N3 H3 O11 . .86 1.95 2.8012(16) 168 yes 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 O12 N1 C11 O11 -8.5(2) O12 N1 C11 C12 170.73(11) O11 C11 C12 C13 -46.0(2) N1 C11 C12 C13 134.74(14) O22 N2 C21 O21 -6.6(2) O22 N2 C21 C22 172.96(12) O21 C21 C22 C23 60.6(2) N2 C21 C22 C23 -118.96(16) O32 N3 C31 O31 -1.6(2) O32 N3 C31 C32 179.98(12) O31 C31 C32 C33 -66.7(2) N3 C31 C32 C33 111.78(17) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 68260 2 PubChem 139058182