############################################################################## # # # This CIF contains the data in a paper accepted for publication in # # Acta Crystallographica Section E. It conforms to the requirements of # # Notes for Authors for Acta Crystallographica Section E, and has been # # peer reviewed under the auspices of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. # # # # Software is freely available for graphical display of the structure(s) # # in this CIF. For information consult the CIF software page # # http://www.iucr.org/resources/cif/software. # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_global _audit_creation_method 'form.cif (version 2.0)' _journal_data_validation_number ? _journal_date_recd_electronic 2013-03-02 _journal_date_accepted 2013-03-07 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2013 _journal_volume 69 _journal_issue 4 _journal_page_first o552 _journal_page_last o552 _journal_paper_category QO _journal_paper_doi 10.1107/S1600536813006569 _journal_coeditor_code RZ5048 _publ_contact_author_name 'Yousuf, S. ' _publ_contact_author_address ; H.E.J. Research Institute of Chemistry, International Cenetr for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan ; _publ_contact_author_email 'dr.sammer.yousuf@gmail.com' _publ_contact_author_fax '+92-21 34819018-9' _publ_contact_author_phone '+92-21 34824924' _publ_section_title ; 1-(2-Methyl-5-nitro-1H-imidazol-1-yl)acetone ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Sammer Yousuf' ? ; H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan ; 'Khalid M. Khan' ? ; H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan ; 'Frazana Naz' ? ; H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan ; 'Shahanaz Perveen' ? ; PCSIR Laboratories Complex Karachi, Shahrah-e-Dr Salimuzzaman Siddiqui, Karachi 75280, Pakistan ; 'Ghulam A. Miana' ? ; Ripha Insititue of Pharmaceutical Sciences, Ripha International University, 7th Avenue G-7/4 Islamambad, Pakistan ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2-Methyl-5-nitro-1H-imidazol-1-yl)acetone ; _chemical_name_common ? _chemical_formula_moiety 'C7 H9 N3 O3' _chemical_formula_sum 'C7 H9 N3 O3' _chemical_formula_iupac 'C7 H9 N3 O3' _chemical_formula_weight 183.17 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.7548(4) _cell_length_b 12.3971(9) _cell_length_c 14.8580(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.350(2) _cell_angle_gamma 90.00 _cell_volume 868.62(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1790 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 26.65 _cell_measurement_temperature 273(2) _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.24 _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_absorpt_correction_T_min 0.9442 _exptl_absorpt_correction_T_max 0.9737 _exptl_special_details ; ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker SMART APEX CCD area-detector ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5030 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > \s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 1614 _reflns_number_gt 1328 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_gt 0.1115 _refine_ls_wR_factor_ref 0.1215 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_number_reflns 1614 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.2124P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.185 _refine_diff_density_min -0.153 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material ; SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009) ; loop_ _atom_site_type_symbol _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_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group O O1 -0.1621(4) 0.29596(12) 0.33611(13) 0.0887(5) Uani d . 1 1 . . O O2 0.1562(3) 0.37418(11) 0.26792(12) 0.0791(5) Uani d . 1 1 . . O O3 -0.2465(3) 0.53369(11) 0.15962(9) 0.0622(4) Uani d . 1 1 . . N N1 -0.0008(3) 0.57463(11) 0.33181(9) 0.0424(4) Uani d . 1 1 . . N N2 -0.2805(3) 0.59824(13) 0.43940(10) 0.0574(4) Uani d . 1 1 . . N N3 -0.0337(3) 0.37691(12) 0.31638(12) 0.0589(4) Uani d . 1 1 . . C C1 -0.1098(3) 0.47575(13) 0.35252(12) 0.0464(4) Uani d . 1 1 . . C C2 -0.2784(4) 0.49243(16) 0.41793(12) 0.0554(5) Uani d . 1 1 . . H H2B -0.3781 0.4389 0.4442 0.067 Uiso calc R 1 1 . . C C3 -0.1137(4) 0.64611(14) 0.38648(11) 0.0485(4) Uani d . 1 1 . . C C4 -0.0467(5) 0.76284(16) 0.38973(15) 0.0728(6) Uani d . 1 1 . . H H4A -0.1214 0.7951 0.4404 0.109 Uiso calc R 1 1 . . H H4B -0.1305 0.7965 0.3346 0.109 Uiso calc R 1 1 . . H H4C 0.1552 0.7725 0.3963 0.109 Uiso calc R 1 1 . . C C5 0.1509(3) 0.60187(13) 0.25566(11) 0.0444(4) Uani d . 1 1 . . H H5A 0.3240 0.5598 0.2597 0.053 Uiso calc R 1 1 . . H H5B 0.2034 0.6775 0.2595 0.053 Uiso calc R 1 1 . . C C6 -0.0235(3) 0.58087(13) 0.16507(12) 0.0451(4) Uani d . 1 1 . . C C7 0.1011(4) 0.62131(17) 0.08469(13) 0.0653(5) Uani d . 1 1 . . H H7A -0.0270 0.6069 0.0307 0.098 Uiso calc R 1 1 . . H H7B 0.2783 0.5855 0.0810 0.098 Uiso calc R 1 1 . . H H7C 0.1326 0.6976 0.0905 0.098 Uiso calc R 1 1 . . 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 O1 0.1009(12) 0.0431(8) 0.1246(15) -0.0117(8) 0.0248(10) 0.0121(8) O2 0.0790(10) 0.0538(9) 0.1115(13) 0.0122(7) 0.0387(9) -0.0036(8) O3 0.0539(8) 0.0678(9) 0.0641(9) -0.0109(6) 0.0049(6) -0.0016(6) N1 0.0423(7) 0.0430(8) 0.0437(8) -0.0021(6) 0.0123(6) 0.0018(6) N2 0.0622(9) 0.0651(10) 0.0487(9) -0.0007(7) 0.0216(7) 0.0031(7) N3 0.0590(9) 0.0430(9) 0.0751(11) 0.0029(7) 0.0098(8) 0.0065(7) C1 0.0465(9) 0.0426(9) 0.0509(10) -0.0010(7) 0.0098(7) 0.0075(7) C2 0.0541(10) 0.0610(12) 0.0530(11) -0.0045(9) 0.0138(8) 0.0145(9) C3 0.0529(9) 0.0508(10) 0.0432(9) -0.0007(8) 0.0112(8) -0.0011(7) C4 0.0993(16) 0.0555(12) 0.0684(14) -0.0068(11) 0.0296(12) -0.0125(10) C5 0.0436(8) 0.0444(9) 0.0479(9) -0.0045(7) 0.0159(7) 0.0003(7) C6 0.0457(9) 0.0395(9) 0.0518(10) 0.0047(7) 0.0124(7) -0.0012(7) C7 0.0693(12) 0.0784(14) 0.0502(11) -0.0027(10) 0.0151(9) 0.0038(10) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; 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 O1 N3 . 1.230(2) ? O2 N3 . 1.225(2) ? O3 C6 . 1.205(2) ? N1 C3 . 1.358(2) ? N1 C1 . 1.381(2) ? N1 C5 . 1.457(2) ? N2 C3 . 1.326(2) ? N2 C2 . 1.350(3) ? N3 C1 . 1.404(2) ? C1 C2 . 1.352(2) ? C2 H2B . 0.9300 ? C3 C4 . 1.481(3) ? C4 H4A . 0.9600 ? C4 H4B . 0.9600 ? C4 H4C . 0.9600 ? C5 C6 . 1.510(2) ? C5 H5A . 0.9700 ? C5 H5B . 0.9700 ? C6 C7 . 1.486(3) ? C7 H7A . 0.9600 ? C7 H7B . 0.9600 ? C7 H7C . 0.9600 ? 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 _geom_angle_publ_flag C3 N1 C1 . . 104.93(14) ? C3 N1 C5 . . 125.87(14) ? C1 N1 C5 . . 128.02(14) ? C3 N2 C2 . . 105.74(15) ? O2 N3 O1 . . 122.92(17) ? O2 N3 C1 . . 119.63(15) ? O1 N3 C1 . . 117.45(17) ? C2 C1 N1 . . 107.35(15) ? C2 C1 N3 . . 127.87(16) ? N1 C1 N3 . . 124.56(15) ? N2 C2 C1 . . 109.97(15) ? N2 C2 H2B . . 125.0 ? C1 C2 H2B . . 125.0 ? N2 C3 N1 . . 112.01(16) ? N2 C3 C4 . . 124.07(16) ? N1 C3 C4 . . 123.86(16) ? C3 C4 H4A . . 109.5 ? C3 C4 H4B . . 109.5 ? H4A C4 H4B . . 109.5 ? C3 C4 H4C . . 109.5 ? H4A C4 H4C . . 109.5 ? H4B C4 H4C . . 109.5 ? N1 C5 C6 . . 112.47(13) ? N1 C5 H5A . . 109.1 ? C6 C5 H5A . . 109.1 ? N1 C5 H5B . . 109.1 ? C6 C5 H5B . . 109.1 ? H5A C5 H5B . . 107.8 ? O3 C6 C7 . . 123.21(16) ? O3 C6 C5 . . 121.44(15) ? C7 C6 C5 . . 115.35(14) ? C6 C7 H7A . . 109.5 ? C6 C7 H7B . . 109.5 ? H7A C7 H7B . . 109.5 ? C6 C7 H7C . . 109.5 ? H7A C7 H7C . . 109.5 ? H7B C7 H7C . . 109.5 ? 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_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C3 N1 C1 C2 . . . . -0.39(18) ? C5 N1 C1 C2 . . . . -168.41(15) ? C3 N1 C1 N3 . . . . -175.31(16) ? C5 N1 C1 N3 . . . . 16.7(3) ? O2 N3 C1 C2 . . . . -168.38(18) ? O1 N3 C1 C2 . . . . 11.0(3) ? O2 N3 C1 N1 . . . . 5.5(3) ? O1 N3 C1 N1 . . . . -175.14(16) ? C3 N2 C2 C1 . . . . 0.3(2) ? N1 C1 C2 N2 . . . . 0.1(2) ? N3 C1 C2 N2 . . . . 174.76(17) ? C2 N2 C3 N1 . . . . -0.6(2) ? C2 N2 C3 C4 . . . . -177.73(19) ? C1 N1 C3 N2 . . . . 0.60(18) ? C5 N1 C3 N2 . . . . 168.96(14) ? C1 N1 C3 C4 . . . . 177.77(18) ? C5 N1 C3 C4 . . . . -13.9(3) ? C3 N1 C5 C6 . . . . -106.10(18) ? C1 N1 C5 C6 . . . . 59.6(2) ? N1 C5 C6 O3 . . . . -9.0(2) ? N1 C5 C6 C7 . . . . 171.59(15) ? 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 C2 H2B N2 3_466 0.9300 2.5600 3.361(2) 144.00 yes C5 H5B O2 2_555 0.9700 2.5700 3.527(2) 167.00 yes C7 H7B O3 1_655 0.9600 2.4900 3.340(2) 147.00 yes _iucr_refine_instructions_details ; TITL I in P2(1)/n CELL 0.71073 4.7548 12.3971 14.8580 90.000 97.350 90.000 ZERR 4.00 0.0004 0.0009 0.0011 0.000 0.002 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 28 36 12 12 TEMP 0 SIZE 0.52 0.33 0.24 OMIT -3 51 L.S. 20 BOND $H CONF ACTA FMAP 2 1 60 PLAN 10 WGHT 0.059100 0.212400 FVAR 0.75187 O1 4 -0.162148 0.295957 0.336108 11.00000 0.10089 0.04313 = 0.12464 0.01211 0.02481 -0.01168 O2 4 0.156180 0.374178 0.267919 11.00000 0.07900 0.05380 = 0.11154 -0.00356 0.03868 0.01216 O3 4 -0.246458 0.533688 0.159620 11.00000 0.05387 0.06777 = 0.06414 -0.00155 0.00485 -0.01085 N1 3 -0.000786 0.574633 0.331805 11.00000 0.04229 0.04298 = 0.04374 0.00178 0.01225 -0.00213 N2 3 -0.280531 0.598238 0.439401 11.00000 0.06223 0.06511 = 0.04871 0.00312 0.02163 -0.00066 N3 3 -0.033670 0.376908 0.316383 11.00000 0.05896 0.04298 = 0.07510 0.00651 0.00982 0.00295 C1 1 -0.109785 0.475746 0.352516 11.00000 0.04651 0.04260 = 0.05095 0.00748 0.00976 -0.00097 C2 1 -0.278366 0.492430 0.417928 11.00000 0.05414 0.06102 = 0.05296 0.01451 0.01381 -0.00451 AFIX 43 H2B 2 -0.378075 0.438927 0.444235 11.00000 -1.20000 AFIX 0 C3 1 -0.113657 0.646105 0.386481 11.00000 0.05292 0.05075 = 0.04323 -0.00112 0.01122 -0.00069 C4 1 -0.046691 0.762840 0.389729 11.00000 0.09929 0.05550 = 0.06837 -0.01247 0.02956 -0.00679 AFIX 137 H4A 2 -0.121357 0.795123 0.440408 11.00000 -1.50000 H4B 2 -0.130535 0.796542 0.334569 11.00000 -1.50000 H4C 2 0.155220 0.772511 0.396316 11.00000 -1.50000 AFIX 0 C5 1 0.150895 0.601873 0.255659 11.00000 0.04359 0.04437 = 0.04788 0.00027 0.01593 -0.00445 AFIX 23 H5A 2 0.323990 0.559758 0.259720 11.00000 -1.20000 H5B 2 0.203444 0.677492 0.259531 11.00000 -1.20000 AFIX 0 C6 1 -0.023452 0.580874 0.165067 11.00000 0.04568 0.03954 = 0.05178 -0.00115 0.01238 0.00470 C7 1 0.101138 0.621310 0.084694 11.00000 0.06928 0.07844 = 0.05018 0.00376 0.01505 -0.00274 AFIX 137 H7A 2 -0.026987 0.606932 0.030693 11.00000 -1.50000 H7B 2 0.278269 0.585491 0.080950 11.00000 -1.50000 H7C 2 0.132600 0.697623 0.090528 11.00000 -1.50000 HKLF 4 REM A in P2(1)/n REM R1 = 0.0414 for 1328 Fo > 4sig(Fo) and 0.0508 for all 1614 data REM 120 parameters refined using 0 restraints END WGHT 0.0591 0.2124 REM Highest difference peak 0.185, deepest hole -0.153, 1-sigma level 0.034 Q1 1 0.2759 0.6583 0.1008 11.00000 0.05 0.18 Q2 1 0.0471 0.7925 0.3383 11.00000 0.05 0.18 Q3 1 -0.2652 0.7982 0.3865 11.00000 0.05 0.16 Q4 1 0.0396 0.7853 0.4644 11.00000 0.05 0.16 Q5 1 -0.1019 0.5097 0.1629 11.00000 0.05 0.12 Q6 1 0.1063 0.5676 0.0342 11.00000 0.05 0.12 Q7 1 -0.2979 0.4790 0.3465 11.00000 0.05 0.12 Q8 1 -0.0923 0.4678 0.4155 11.00000 0.05 0.12 Q9 1 0.1710 0.5505 0.0599 11.00000 0.05 0.10 Q10 1 -0.1009 0.5259 0.3238 11.00000 0.05 0.10 ;