#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011337.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_2011337 loop_ _publ_author_name 'Gzella, Andrzej' 'Wrzeciono, Urszula' 'P\"oppel, Wolfram' _publ_section_title ; Azole. 44. \"Uber Morpholinonitroimidazolderivate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1161 _journal_page_last 1163 _journal_paper_doi 10.1107/S0108270100008635 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C10 H15 Cl N4 O4' _chemical_formula_sum 'C10 H15 Cl N4 O4' _chemical_formula_weight 290.71 _chemical_name_systematic ; 3-Chloro-1-(4-morpholinyl-5-nitroimidazol-1-yl)propan-2-ol ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 106.470(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.6840(8) _cell_length_b 5.2868(8) _cell_length_c 12.8212(7) _cell_measurement_reflns_used 55 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 31.8 _cell_measurement_theta_min 16.8 _cell_volume 629.48(12) _computing_cell_refinement 'Kuma KM-4 Software' _computing_data_collection 'Kuma KM-4 Software (Kuma Diffraction, 1991)' _computing_data_reduction 'Kuma KM-4 Software' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .995 _diffrn_measured_fraction_theta_max .995 _diffrn_measurement_device_type 'Kuma Diffraction KM-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .032 _diffrn_reflns_av_sigmaI/netI .015 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2286 _diffrn_reflns_theta_full 70.11 _diffrn_reflns_theta_max 70.11 _diffrn_reflns_theta_min 3.59 _diffrn_standards_decay_% .8 _diffrn_standards_interval_count 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 2.878 _exptl_absorpt_correction_T_max .750 _exptl_absorpt_correction_T_min .511 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 304 _exptl_crystal_size_max .54 _exptl_crystal_size_mid .17 _exptl_crystal_size_min .10 _refine_diff_density_max .17 _refine_diff_density_min -.26 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack .344(13) _refine_ls_extinction_coef .0246(15) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 178 _refine_ls_number_reflns 2245 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all .026 _refine_ls_R_factor_gt .025 _refine_ls_shift/su_max .010 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.0886P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .072 _reflns_number_gt 2201 _reflns_number_total 2245 _reflns_threshold_expression I>2\s(I) _cod_data_source_file jz1415.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 629.48(11) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2011337 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 .25344(13) .2996(3) .44535(10) .0324(3) Uani d . 1 . . N C2 .35945(16) .1446(4) .49604(12) .0364(3) Uani d . 1 . . C H2A .4013 .0288 .4596 .044 Uiso calc . 1 . . H N3 .39995(14) .1702(3) .60289(11) .0360(3) Uani d . 1 . . N C4 .31146(15) .3495(3) .62562(12) .0316(3) Uani d . 1 . . C C5 .22027(15) .4378(3) .52711(12) .0315(3) Uani d . 1 . . C C6 .17975(16) .2867(3) .32829(12) .0346(3) Uani d . 1 . . C H6A .0845 .3606 .3142 .042 Uiso calc . 1 . . H H6B .1685 .1111 .3055 .042 Uiso calc . 1 . . H C7 .26426(16) .4268(3) .26313(12) .0341(3) Uani d . 1 . . C H7A .2771 .6024 .2885 .041 Uiso calc . 1 . . H C8 .1863(2) .4274(4) .14286(13) .0437(4) Uani d . 1 . . C H8A .2432 .5202 .1045 .052 Uiso calc . 1 . . H H8B .0950 .5146 .1313 .052 Uiso calc . 1 . . H Cl9 .15358(5) .11495(11) .08745(3) .05587(16) Uani d . 1 . . Cl O10 .40081(13) .3153(3) .28177(10) .0419(3) Uani d . 1 . . O H10A .462(3) .395(5) .3097(19) .049(7) Uiso d . 1 . . H N11 .32214(13) .4247(3) .72854(10) .0363(3) Uani d . 1 . . N C12 .45195(17) .3614(3) .81480(12) .0362(3) Uani d . 1 . . C H12A .5354 .3695 .7873 .043 Uiso calc . 1 . . H H12B .4446 .1910 .8408 .043 Uiso calc . 1 . . H C13 .46770(18) .5472(4) .90583(13) .0403(4) Uani d . 1 . . C H13A .5519 .5035 .9648 .048 Uiso calc . 1 . . H H13B .4828 .7148 .8803 .048 Uiso calc . 1 . . H O14 .34471(13) .5516(3) .94579(10) .0488(3) Uani d . 1 . . O C15 .21984(19) .6160(5) .86044(15) .0494(4) Uani d . 1 . . C H15A .2313 .7843 .8340 .059 Uiso calc . 1 . . H H15B .1367 .6180 .8884 .059 Uiso calc . 1 . . H C16 .19449(17) .4310(4) .76809(13) .0417(4) Uani d . 1 . . C H16A .1763 .2640 .7927 .050 Uiso calc . 1 . . H H16B .1110 .4818 .7099 .050 Uiso calc . 1 . . H N17 .14224(13) .6623(3) .50655(11) .0351(3) Uani d . 1 . . N O18 .11854(15) .7774(3) .58335(11) .0509(3) Uani d . 1 . . O O19 .10343(15) .7434(3) .41192(11) .0492(3) Uani d . 1 . . O 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 N1 .0317(6) .0353(7) .0286(6) .0005(5) .0060(5) -.0009(5) C2 .0366(7) .0351(8) .0369(8) .0061(7) .0092(6) -.0013(7) N3 .0350(6) .0350(8) .0356(6) .0068(6) .0063(5) .0009(6) C4 .0295(6) .0318(8) .0319(7) .0004(6) .0062(5) .0002(6) C5 .0300(6) .0327(8) .0309(7) .0022(6) .0073(5) .0011(6) C6 .0325(7) .0407(9) .0283(7) -.0067(7) .0049(5) -.0012(6) C7 .0362(7) .0340(8) .0324(7) -.0055(6) .0103(6) -.0020(6) C8 .0492(9) .0483(10) .0333(8) -.0023(8) .0109(6) .0045(7) Cl9 .0524(3) .0688(3) .0433(2) -.0123(2) .00850(17) -.0192(2) O10 .0322(6) .0464(8) .0471(7) -.0075(5) .0110(5) -.0112(6) N11 .0309(6) .0478(8) .0290(6) .0055(6) .0064(5) -.0010(6) C12 .0354(7) .0393(9) .0309(7) .0051(6) .0046(6) .0025(6) C13 .0405(8) .0488(10) .0316(7) -.0037(7) .0102(6) -.0026(7) O14 .0475(7) .0691(9) .0329(6) -.0036(6) .0164(5) -.0027(6) C15 .0435(9) .0637(12) .0450(9) .0055(9) .0190(7) -.0047(9) C16 .0338(7) .0534(10) .0389(8) -.0010(7) .0121(6) .0008(8) N17 .0314(6) .0319(7) .0411(7) .0037(6) .0088(5) .0047(6) O18 .0546(7) .0446(8) .0558(8) .0154(6) .0193(6) -.0037(6) O19 .0543(7) .0433(7) .0473(7) .0109(6) .0098(5) .0170(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 '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 .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .3639 .7018 '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 _geom_angle_publ_flag C2 N1 C5 105.48(12) yes C2 N1 C6 123.67(14) ? C5 N1 C6 130.28(13) ? N3 C2 N1 113.89(14) yes C2 N3 C4 105.83(13) yes N11 C4 N3 122.24(14) ? N11 C4 C5 129.48(15) ? N3 C4 C5 108.23(13) yes N1 C5 N17 122.36(13) ? N1 C5 C4 106.50(13) yes N17 C5 C4 128.68(14) ? N1 C6 C7 110.98(12) ? O10 C7 C8 110.39(13) ? O10 C7 C6 109.28(14) ? C8 C7 C6 111.77(13) ? C7 C8 Cl9 112.55(13) ? C7 O10 H10A 116(2) ? C4 N11 C12 118.88(13) ? C4 N11 C16 120.38(13) ? C12 N11 C16 111.94(12) ? N11 C12 C13 108.38(14) ? O14 C13 C12 112.32(14) ? C15 O14 C13 110.02(12) ? O14 C15 C16 111.35(17) ? N11 C16 C15 108.82(14) ? O18 N17 O19 122.50(15) ? O18 N17 C5 118.92(13) ? O19 N17 C5 118.54(13) ? 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 N1 C2 . 1.330(2) yes N1 C5 . 1.388(2) yes N1 C6 . 1.4693(18) ? C2 N3 . 1.321(2) yes N3 C4 . 1.364(2) yes C4 N11 . 1.354(2) yes C4 C5 . 1.400(2) yes C5 N17 . 1.391(2) yes C6 C7 . 1.518(2) ? C7 O10 . 1.405(2) ? C7 C8 . 1.512(2) ? C8 Cl9 . 1.791(2) yes O10 H10A . .73(3) ? N11 C12 . 1.4585(19) ? N11 C16 . 1.4634(19) ? C12 C13 . 1.500(2) ? C13 O14 . 1.424(2) ? O14 C15 . 1.423(2) ? C15 C16 . 1.501(3) ? N17 O18 . 1.2331(18) ? N17 O19 . 1.2403(18) ? 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 O10 H10A N3 2_656 .73(3) 2.08(3) 2.7948(19) 167(3) yes C6 H6B O19 1_545 .97 2.55 3.224(2) 126 yes C8 H8A O14 1_554 .97 2.50 3.372(2) 149 yes C16 H16B O18 . .97 2.27 2.918(2) 124 yes C16 H16B O19 2_546 .97 2.55 3.295(2) 134 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 C5 N1 C2 N3 -.76(19) C6 N1 C2 N3 -172.93(14) N1 C2 N3 C4 2.1(2) C2 N3 C4 N11 179.97(16) C2 N3 C4 C5 -2.49(18) C2 N1 C5 N17 162.78(15) C6 N1 C5 N17 -25.8(2) C2 N1 C5 C4 -.84(17) C6 N1 C5 C4 170.61(15) N11 C4 C5 N1 179.38(16) N3 C4 C5 N1 2.08(17) N11 C4 C5 N17 17.1(3) N3 C4 C5 N17 -160.15(15) C2 N1 C6 C7 -83.3(2) C5 N1 C6 C7 106.64(17) N1 C6 C7 O10 60.52(17) N1 C6 C7 C8 -176.99(15) O10 C7 C8 Cl9 62.41(16) C6 C7 C8 Cl9 -59.45(17) N3 C4 N11 C12 15.4(2) C5 C4 N11 C12 -161.53(16) N3 C4 N11 C16 -129.44(18) C5 C4 N11 C16 53.6(3) C4 N11 C12 C13 156.38(15) C16 N11 C12 C13 -55.97(19) N11 C12 C13 O14 56.87(18) C12 C13 O14 C15 -58.9(2) C13 O14 C15 C16 58.9(2) C4 N11 C16 C15 -156.19(17) C12 N11 C16 C15 56.7(2) O14 C15 C16 N11 -57.5(2) N1 C5 N17 O18 -178.89(14) C4 C5 N17 O18 -19.1(2) N1 C5 N17 O19 -1.3(2) C4 C5 N17 O19 158.41(16) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21179982 2 PubChem 139057920