#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/13/2011338.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_2011338 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-(5-morpholinyl-4-nitroimidazol-1-yl)propan-2-ol ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL97 _cell_angle_alpha 91.101(9) _cell_angle_beta 101.026(10) _cell_angle_gamma 101.940(10) _cell_formula_units_Z 2 _cell_length_a 6.5036(8) _cell_length_b 7.8493(9) _cell_length_c 12.9757(14) _cell_measurement_reflns_used 43 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 30.0 _cell_measurement_theta_min 11.3 _cell_volume 634.91(13) _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 .950 _diffrn_measured_fraction_theta_max .950 _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 .022 _diffrn_reflns_av_sigmaI/netI .015 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2386 _diffrn_reflns_theta_full 70.04 _diffrn_reflns_theta_max 70.04 _diffrn_reflns_theta_min 3.48 _diffrn_standards_decay_% 3.8 _diffrn_standards_interval_count 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 2.853 _exptl_absorpt_correction_T_max .867 _exptl_absorpt_correction_T_min .440 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 304 _exptl_crystal_size_max .38 _exptl_crystal_size_mid .27 _exptl_crystal_size_min .05 _refine_diff_density_max .36 _refine_diff_density_min -.28 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 176 _refine_ls_number_reflns 2281 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all .048 _refine_ls_R_factor_gt .041 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0695P)^2^+0.2622P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .122 _reflns_number_gt 2036 _reflns_number_total 2281 _reflns_threshold_expression I>2\s(I) _cod_data_source_file jz1415.cif _cod_data_source_block III _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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_database_code 2011338 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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 .8161(2) .51309(19) .14522(12) .0354(3) Uani d . 1 . . N C2 .7643(3) .5726(2) .04814(15) .0379(4) Uani d . 1 . . C H2A .7488 .6863 .0368 .046 Uiso calc . 1 . . H N3 .7385(2) .4537(2) -.02739(12) .0396(4) Uani d . 1 . . N C4 .7703(3) .3077(2) .02411(14) .0364(4) Uani d . 1 . . C C5 .8218(3) .3398(2) .13179(14) .0338(4) Uani d . 1 . . C C6 .8466(3) .6089(2) .24612(15) .0386(4) Uani d . 1 . . C H6A .9424 .7213 .2456 .046 Uiso calc . 1 . . H H6B .9132 .5448 .3014 .046 Uiso calc . 1 . . H C7 .6325(3) .6369(2) .26959(14) .0387(4) Uani d . 1 . . C H7A .5964 .7392 .2344 .046 Uiso calc . 1 . . H C8 .6605(4) .6696(3) .38694(16) .0502(5) Uani d . 1 . . C H8A .7863 .7616 .4119 .060 Uiso calc . 1 . . H H8B .6834 .5647 .4216 .060 Uiso calc . 1 . . H Cl9 .43074(12) .73111(11) .42040(5) .0762(3) Uani d . 1 . . Cl O10 .4646(2) .49088(19) .23518(12) .0462(4) Uani d . 1 . . O H10A .389(5) .512(4) .175(2) .071(9) Uiso d . 1 . . H N11 .7442(3) .1472(2) -.03436(13) .0439(4) Uani d . 1 . . N O12 .7421(3) .0135(2) .01360(14) .0599(4) Uani d . 1 . . O O13 .7223(3) .1494(2) -.13030(12) .0661(5) Uani d . 1 . . O N14 .8900(3) .2497(2) .21725(12) .0368(4) Uani d . 1 . . N C15 .7373(3) .1714(3) .28089(16) .0436(5) Uani d . 1 . . C H15A .6553 .0594 .2483 .052 Uiso calc . 1 . . H H15B .6384 .2465 .2867 .052 Uiso calc . 1 . . H C16 .8614(4) .1479(3) .38845(19) .0571(6) Uani d . 1 . . C H16A .9332 .2613 .4226 .068 Uiso calc . 1 . . H H16B .7629 .0911 .4310 .068 Uiso calc . 1 . . H O17 1.0168(3) .0456(2) .38198(13) .0600(5) Uani d . 1 . . O C18 1.1640(4) .1254(3) .32027(18) .0507(5) Uani d . 1 . . C H18A 1.2689 .0547 .3176 .061 Uiso calc . 1 . . H H18B 1.2396 .2391 .3528 .061 Uiso calc . 1 . . H C19 1.0502(3) .1458(3) .21028(16) .0439(5) Uani d . 1 . . C H19A 1.1520 .2039 .1698 .053 Uiso calc . 1 . . H H19B .9809 .0322 .1756 .053 Uiso calc . 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 N1 .0401(8) .0308(8) .0360(8) .0085(7) .0082(6) .0034(6) C2 .0368(9) .0372(10) .0414(10) .0095(8) .0093(7) .0093(7) N3 .0356(8) .0477(9) .0373(8) .0128(7) .0074(6) .0066(7) C4 .0336(9) .0397(10) .0367(9) .0095(8) .0070(7) .0001(7) C5 .0334(9) .0326(9) .0367(9) .0074(7) .0095(7) .0025(7) C6 .0424(10) .0322(9) .0390(9) .0069(8) .0041(7) -.0013(7) C7 .0452(11) .0330(9) .0373(9) .0101(8) .0052(8) .0014(7) C8 .0545(12) .0578(13) .0404(11) .0191(10) .0073(9) -.0023(9) Cl9 .0755(5) .1039(6) .0603(4) .0367(4) .0231(3) -.0085(3) O10 .0460(8) .0439(8) .0457(8) .0068(6) .0050(6) .0047(6) N11 .0394(9) .0478(10) .0444(9) .0134(7) .0044(7) -.0064(7) O12 .0669(11) .0411(9) .0676(10) .0133(8) .0025(8) -.0075(7) O13 .0807(12) .0767(12) .0430(9) .0301(10) .0046(8) -.0142(8) N14 .0394(8) .0371(8) .0384(8) .0139(7) .0118(6) .0088(6) C15 .0424(11) .0421(11) .0521(11) .0132(9) .0179(9) .0140(8) C16 .0650(14) .0686(15) .0511(12) .0303(12) .0255(11) .0227(11) O17 .0653(10) .0716(11) .0591(9) .0355(9) .0257(8) .0334(8) C18 .0454(11) .0594(13) .0528(12) .0207(10) .0115(9) .0172(10) C19 .0461(11) .0478(11) .0459(10) .0213(9) .0161(8) .0111(8) 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 107.45(15) yes C2 N1 C6 127.10(15) ? C5 N1 C6 125.33(15) ? N3 C2 N1 112.92(16) yes C2 N3 C4 103.95(15) yes N3 C4 C5 112.18(16) yes N3 C4 N11 119.78(16) ? C5 C4 N11 128.02(17) ? N1 C5 N14 120.03(16) ? N1 C5 C4 103.47(15) yes N14 C5 C4 136.16(17) ? N1 C6 C7 111.54(15) ? O10 C7 C8 109.33(17) ? O10 C7 C6 111.85(15) ? C8 C7 C6 108.05(16) ? C7 C8 Cl9 111.27(15) ? C7 O10 H10A 108.8(19) ? O13 N11 O12 123.55(18) ? O13 N11 C4 118.07(18) ? O12 N11 C4 118.38(17) ? C5 N14 C15 119.37(15) ? C5 N14 C19 118.71(15) ? C15 N14 C19 112.40(14) ? N14 C15 C16 108.18(17) ? O17 C16 C15 111.35(18) ? C18 O17 C16 110.78(16) ? O17 C18 C19 111.02(18) ? N14 C19 C18 108.05(16) ? 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 . 1.358(2) yes N1 C5 . 1.377(2) yes N1 C6 . 1.456(2) ? C2 N3 . 1.303(3) yes N3 C4 . 1.370(2) yes C4 C5 . 1.379(3) yes C4 N11 . 1.421(2) yes C5 N14 . 1.378(2) yes C6 C7 . 1.538(3) ? C7 O10 . 1.407(2) ? C7 C8 . 1.509(3) ? C8 Cl9 . 1.787(2) yes O10 H10A . .88(3) ? N11 O13 . 1.227(2) ? N11 O12 . 1.229(2) ? N14 C15 . 1.458(2) ? N14 C19 . 1.463(2) ? C15 C16 . 1.508(3) ? C16 O17 . 1.427(3) ? O17 C18 . 1.419(3) ? C18 C19 . 1.505(3) ? 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_665 .88(3) 1.98(3) 2.850(2) 169(3) yes C7 H7A O13 2_665 .98 2.57 3.396(2) 142 yes C8 H8A O17 1_565 .97 2.50 3.364(3) 149 yes C15 H15B O10 . .97 2.46 3.359(2) 154 yes C19 H19B O12 . .97 2.34 2.947(3) 120 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 -.9(2) C6 N1 C2 N3 -177.08(17) N1 C2 N3 C4 1.6(2) C2 N3 C4 C5 -1.7(2) C2 N3 C4 N11 176.94(17) C2 N1 C5 N14 174.00(16) C6 N1 C5 N14 -9.7(3) C2 N1 C5 C4 -.3(2) C6 N1 C5 C4 176.04(16) N3 C4 C5 N1 1.3(2) N11 C4 C5 N1 -177.31(18) N3 C4 C5 N14 -171.6(2) N11 C4 C5 N14 9.9(4) C2 N1 C6 C7 71.6(2) C5 N1 C6 C7 -103.9(2) N1 C6 C7 O10 37.7(2) N1 C6 C7 C8 158.05(16) O10 C7 C8 Cl9 -65.47(19) C6 C7 C8 Cl9 172.58(14) N3 C4 N11 O13 9.8(3) C5 C4 N11 O13 -171.78(19) N3 C4 N11 O12 -169.34(17) C5 C4 N11 O12 9.1(3) N1 C5 N14 C15 85.0(2) C4 C5 N14 C15 -103.1(3) N1 C5 N14 C19 -131.23(19) C4 C5 N14 C19 40.7(3) C5 N14 C15 C16 -157.27(18) C19 N14 C15 C16 56.8(2) N14 C15 C16 O17 -56.5(2) C15 C16 O17 C18 59.1(3) C16 O17 C18 C19 -59.8(3) C5 N14 C19 C18 156.31(18) C15 N14 C19 C18 -57.5(2) O17 C18 C19 N14 57.9(2)