#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/89/2008923.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_2008923 loop_ _publ_author_name 'Gzella, Andrzej' 'Wrzeciono, Urszula' 'P\"oppel, Wolfram' _publ_section_title ; Azole. 42. \"Uber Nitropiperidinoimidazolderivate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1562 _journal_page_last 1565 _journal_paper_doi 10.1107/S0108270199005880 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C6 H7 Cl N4 O5' _chemical_formula_sum 'C6 H7 Cl N4 O5' _chemical_formula_weight 250.61 _chemical_name_systematic ; 3-chloro-1-(4,5-dinitroimidazolyl)propan-2-ol ; _space_group_IT_number 29 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _audit_creation_method SHELXL93 _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_formula_units_Z 4 _cell_length_a 10.3098(13) _cell_length_b 8.4972(8) _cell_length_c 11.4264(13) _cell_measurement_reflns_used 48 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 30.0 _cell_measurement_theta_min 13.8 _cell_volume 1001.00(19) _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 'ORTEPII (Johnson, 1976) and PLUTO (Motherwell & Clegg, 1978)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Kuma Diffraction KM-4' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_av_sigmaI/netI 0.009 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 1733 _diffrn_reflns_theta_max 70.14 _diffrn_reflns_theta_min 5.21 _diffrn_standards_decay_% 2.5 _diffrn_standards_interval_count 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 3.595 _exptl_absorpt_correction_T_max 0.505 _exptl_absorpt_correction_T_min 0.192 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.344 _refine_diff_density_min -0.231 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.089 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 1733 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.089 _refine_ls_restrained_S_obs 1.094 _refine_ls_R_factor_all 0.038 _refine_ls_R_factor_gt 0.037 _refine_ls_shift/esd_mean 0.000 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.23P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.108 _reflns_number_gt 1691 _reflns_number_total 1733 _reflns_observed_criterion I>2\s(I) _cod_data_source_file jz1330.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 'Orthorhombic' changed to 'orthorhombic' 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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.23P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.23P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1001.0(2) _cod_database_code 2008923 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' '-x, -y, z+1/2' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0696(13) 0.0465(11) 0.0478(10) -0.0011(10) 0.0062(10) 0.0038(10) C2 0.077(2) 0.059(2) 0.0472(13) 0.0053(12) -0.0004(13) 0.0144(14) N3 0.0696(13) 0.0630(13) 0.0447(11) -0.0011(10) -0.0066(10) 0.0049(11) C4 0.0608(14) 0.0490(13) 0.0446(12) -0.0037(10) 0.0033(11) 0.0029(11) C5 0.0543(13) 0.0493(12) 0.0475(12) -0.0041(10) 0.0045(10) 0.0017(11) C6 0.075(2) 0.0441(14) 0.058(2) 0.0001(12) 0.0116(13) -0.0007(12) C7 0.0539(14) 0.0478(12) 0.0595(14) -0.0028(13) 0.0080(12) -0.0024(10) C8 0.066(2) 0.057(2) 0.077(2) -0.0173(15) 0.007(2) -0.0030(13) Cl9 0.1094(7) 0.0520(4) 0.0920(6) -0.0056(4) 0.0217(5) 0.0098(4) O10 0.0729(13) 0.0604(12) 0.0641(12) 0.0053(10) 0.0143(11) 0.0078(10) N11 0.0699(14) 0.0509(11) 0.0530(12) -0.0076(10) -0.0027(11) 0.0006(11) O12 0.103(2) 0.0599(11) 0.084(2) -0.0109(12) -0.0262(14) -0.0086(12) O13 0.0729(14) 0.0621(12) 0.104(2) -0.0179(12) -0.0044(12) 0.0154(10) N14 0.0599(13) 0.0597(14) 0.0639(13) -0.0165(12) -0.0060(11) 0.0048(11) O15 0.101(2) 0.0637(12) 0.090(2) 0.0028(13) -0.040(2) 0.0074(12) O16 0.0593(11) 0.094(2) 0.089(2) -0.0230(14) 0.0023(12) -0.0104(12) loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.6513(2) 0.6445(3) 0.0120(2) 0.0546(5) Uani 1 d . . C2 C 0.5590(3) 0.6171(4) -0.0705(3) 0.0612(7) Uani 1 d . . H2A H 0.5118(35) 0.6881(47) -0.1018(33) 0.063(9) Uiso 1 d . . N3 N 0.5529(2) 0.4688(3) -0.1025(2) 0.0591(6) Uani 1 d . . C4 C 0.6461(3) 0.3979(3) -0.0387(2) 0.0514(6) Uani 1 d . . C5 C 0.7058(2) 0.5015(3) 0.0336(2) 0.0504(6) Uani 1 d . . C6 C 0.6740(3) 0.7947(3) 0.0723(3) 0.0592(7) Uani 1 d . . H6A H 0.6474(32) 0.8659(39) 0.0267(31) 0.052(8) Uiso 1 d . . H6B H 0.7695(34) 0.8136(37) 0.0836(31) 0.058(8) Uiso 1 d . . C7 C 0.6079(3) 0.7992(3) 0.1905(3) 0.0537(6) Uani 1 d . . H7A H 0.5205(26) 0.7908(30) 0.1780(23) 0.034(6) Uiso 1 d . . C8 C 0.6378(3) 0.9525(4) 0.2514(3) 0.0666(8) Uani 1 d . . H8A H 0.7304(41) 0.9849(43) 0.2488(35) 0.076(10) Uiso 1 d . . H8B H 0.6149(38) 0.9376(49) 0.3426(38) 0.075(10) Uiso 1 d . . Cl9 Cl 0.54038(10) 1.10881(9) 0.19537(9) 0.0845(3) Uani 1 d . . O10 O 0.6558(3) 0.6721(3) 0.2572(2) 0.0658(5) Uani 1 d . . H10A H 0.6070(50) 0.6279(54) 0.2895(46) 0.087(16) Uiso 1 d . . N11 N 0.6758(2) 0.2337(3) -0.0561(2) 0.0579(6) Uani 1 d . . O12 O 0.5950(3) 0.1521(3) -0.1014(2) 0.0825(7) Uani 1 d . . O13 O 0.7815(2) 0.1873(3) -0.0250(3) 0.0795(7) Uani 1 d . . N14 N 0.8085(2) 0.4774(3) 0.1182(2) 0.0612(6) Uani 1 d . . O15 O 0.8004(3) 0.3622(3) 0.1793(3) 0.0849(8) Uani 1 d . . O16 O 0.8957(2) 0.5733(4) 0.1208(3) 0.0808(7) Uani 1 d . . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 C2 N1 C5 105.2(2) C2 N1 C6 125.8(3) C5 N1 C6 128.6(3) N3 C2 N1 113.0(3) N3 C2 H2A 122.(3) N1 C2 H2A 125.(3) C2 N3 C4 104.1(2) N3 C4 C5 111.3(2) N3 C4 N11 120.6(2) C5 C4 N11 128.0(2) C4 C5 N1 106.4(2) C4 C5 N14 130.3(2) N1 C5 N14 123.3(2) N1 C6 C7 111.7(2) N1 C6 H6A 106.(2) C7 C6 H6A 113.(2) N1 C6 H6B 110.8(18) C7 C6 H6B 109.(2) H6A C6 H6B 106.(3) O10 C7 C8 109.9(3) O10 C7 C6 107.7(2) C8 C7 C6 110.0(2) O10 C7 H7A 111.6(16) C8 C7 H7A 109.9(16) C6 C7 H7A 107.6(17) C7 C8 Cl9 111.2(2) C7 C8 H8A 115.(2) Cl9 C8 H8A 109.(2) C7 C8 H8B 108.(2) Cl9 C8 H8B 108.(2) H8A C8 H8B 106.(3) C7 O10 H10A 115.(4) O12 N11 O13 124.2(2) O12 N11 C4 118.1(2) O13 N11 C4 117.7(2) O15 N14 O16 125.6(3) O15 N14 C5 116.8(2) O16 N14 C5 117.6(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.360(4) . ? N1 C5 1.361(3) . ? N1 C6 1.469(4) . ? C2 N3 1.314(4) . ? C2 H2A 0.85(4) . ? N3 C4 1.348(4) . ? C4 C5 1.356(4) . ? C4 N11 1.442(3) . ? C5 N14 1.448(4) . ? C6 C7 1.513(4) . ? C6 H6A 0.84(4) . ? C6 H6B 1.01(3) . ? C7 O10 1.411(4) . ? C7 C8 1.509(4) . ? C7 H7A 0.92(3) . ? C8 Cl9 1.784(3) . ? C8 H8A 0.99(4) . ? C8 H8B 1.08(4) . ? O10 H10A 0.73(5) . ? N11 O12 1.202(3) . ? N11 O13 1.213(3) . ? N14 O15 1.205(4) . ? N14 O16 1.213(4) . ? 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 4_665 0.73(5) 2.22(5) 2.938(4) 171(5) yes C6 H6B O16 . 1.01(3) 2.46(3) 3.011(4) 114(2) yes C8 H8B O12 4_665 1.08(4) 2.38(4) 3.062(4) 120(3) 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 -0.7(3) C6 N1 C2 N3 -174.4(3) N1 C2 N3 C4 -0.6(3) C2 N3 C4 C5 1.6(3) C2 N3 C4 N11 -175.4(2) N3 C4 C5 N1 -2.1(3) N11 C4 C5 N1 174.7(2) N3 C4 C5 N14 178.8(3) N11 C4 C5 N14 -4.5(5) C2 N1 C5 C4 1.6(3) C6 N1 C5 C4 175.1(2) C2 N1 C5 N14 -179.1(2) C6 N1 C5 N14 -5.6(4) C2 N1 C6 C7 97.0(4) C5 N1 C6 C7 -75.3(4) N1 C6 C7 O10 58.0(3) N1 C6 C7 C8 177.8(3) O10 C7 C8 Cl9 -162.8(2) C6 C7 C8 Cl9 78.7(3) N3 C4 N11 O12 -21.0(4) C5 C4 N11 O12 162.5(3) N3 C4 N11 O13 158.3(3) C5 C4 N11 O13 -18.2(4) C4 C5 N14 O15 -43.0(4) N1 C5 N14 O15 138.0(3) C4 C5 N14 O16 136.2(3) N1 C5 N14 O16 -42.8(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4421890 2 PubChem 139056783