#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/17/2011705.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_2011705 loop_ _publ_author_name 'Kubicki, Maciej' 'Borowiak, Teresa' 'Suwi\'nski, Jerzy' 'Wagner, Pawe\/l' _publ_section_title ; Two 1-substituted 4-nitroimidazoles ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 106 _journal_page_last 108 _journal_paper_doi 10.1107/S0108270100014852 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C9 H7 N3 O2' _chemical_formula_sum 'C9 H7 N3 O2' _chemical_formula_weight 189.18 _chemical_name_systematic ; 1-phenyl-4-nitroimidazole ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 11.088(2) _cell_length_b 6.8840(10) _cell_length_c 21.976(4) _cell_measurement_reflns_used 1027 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 50 _cell_measurement_theta_min 1 _cell_volume 1677.4(5) _computing_cell_refinement 'CrysAlis Red (KUMA Diffraction, 1999)' _computing_data_collection 'CrysAlis CCD (KUMA Diffraction, 1999)' _computing_data_reduction 'CrysAlis Red' _computing_molecular_graphics 'Stereochemical Workstation (Siemens, 1989)' _computing_publication_material 'Stereochemical Workstation' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full .997 _diffrn_measured_fraction_theta_max .997 _diffrn_measurement_device_type 'KUMA KM4-CCD diffractometer' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0460 _diffrn_reflns_av_sigmaI/netI .0293 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 8680 _diffrn_reflns_theta_full 27.10 _diffrn_reflns_theta_max 27.10 _diffrn_reflns_theta_min 3.60 _diffrn_standards_decay_% 'not measured' _diffrn_standards_interval_count '50 frames' _diffrn_standards_number '2 frames' _exptl_absorpt_coefficient_mu .110 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 784 _exptl_crystal_size_max .5 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _refine_diff_density_max .223 _refine_diff_density_min -.227 _refine_ls_extinction_coef .0045(13) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 1846 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.079 _refine_ls_R_factor_all .0504 _refine_ls_R_factor_gt .0349 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0573P)^2^+0.0033P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .0957 _reflns_number_gt 1424 _reflns_number_total 1846 _reflns_threshold_expression I>2\s(I) _cod_data_source_file de1151.cif _cod_data_source_block I _cod_database_code 2011705 _cod_database_fobs_code 2011705 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, 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 N2 .84427(9) .09313(16) .58588(5) .0230(3) Uani d . 1 . . N O2 .95214(8) .09132(15) .59995(4) .0318(3) Uani d . 1 . . O N3 .69680(9) .18320(16) .50867(5) .0227(3) Uani d . 1 . . N O1 .76318(9) .03601(16) .61899(4) .0352(3) Uani d . 1 . . O N1 .82342(9) .26126(14) .43359(4) .0195(3) Uani d . 1 . . N C5 .89461(11) .21182(18) .48199(5) .0197(3) Uani d . 1 . . C C6 .86295(11) .32408(18) .37463(5) .0203(3) Uani d . 1 . . C C11 .97382(12) .4141(2) .36843(6) .0238(3) Uani d . 1 . . C C8 .82550(13) .3578(2) .26806(6) .0278(3) Uani d . 1 . . C C2 .70604(11) .24310(19) .45225(6) .0222(3) Uani d . 1 . . C C9 .93557(13) .4503(2) .26129(6) .0284(3) Uani d . 1 . . C C4 .81398(11) .16430(18) .52645(5) .0201(3) Uani d . 1 . . C C7 .78864(13) .2936(2) .32475(6) .0243(3) Uani d . 1 . . C C10 1.00987(13) .4773(2) .31126(6) .0280(3) Uani d . 1 . . C H111 1.0254(12) .431(2) .4019(6) .027(4) Uiso d . 1 . . H H21 .6390(13) .270(2) .4265(6) .029(4) Uiso d . 1 . . H H71 .7102(13) .231(2) .3301(6) .023(4) Uiso d . 1 . . H H81 .7721(14) .340(2) .2324(7) .031(4) Uiso d . 1 . . H H51 .9803(14) .214(2) .4802(6) .028(4) Uiso d . 1 . . H H101 1.0879(14) .547(2) .3059(6) .037(4) Uiso d . 1 . . H H91 .9607(13) .498(2) .2223(7) .032(4) Uiso d . 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 N2 .0208(6) .0288(6) .0195(6) -.0006(4) .0019(4) -.0013(4) O2 .0215(5) .0488(7) .0251(5) -.0014(4) -.0027(4) .0065(4) N3 .0184(6) .0260(6) .0237(6) .0007(4) .0018(4) -.0018(4) O1 .0277(5) .0551(7) .0230(5) -.0045(5) .0069(4) .0072(5) N1 .0195(5) .0210(6) .0180(5) .0000(4) -.0003(4) -.0001(4) C5 .0176(7) .0229(7) .0188(6) .0011(5) -.0012(4) -.0001(5) C6 .0237(7) .0193(6) .0178(6) .0032(5) .0004(5) .0004(5) C11 .0227(7) .0286(7) .0199(7) .0008(5) -.0018(5) .0007(5) C8 .0348(8) .0291(7) .0195(6) .0057(6) -.0052(5) -.0024(5) C2 .0183(6) .0243(7) .0240(6) .0005(5) -.0011(5) -.0019(5) C9 .0350(8) .0305(8) .0196(7) .0074(6) .0045(5) .0033(6) C4 .0201(6) .0210(6) .0192(6) .0002(5) .0002(5) -.0013(5) C7 .0259(7) .0237(7) .0235(7) -.0005(5) -.0034(5) -.0021(5) C10 .0260(7) .0316(8) .0264(7) .0008(6) .0041(5) .0041(6) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O1 N2 O2 124.07(11) ? O1 N2 C4 118.67(10) ? O2 N2 C4 117.25(10) ? C2 N3 C4 103.10(10) ? C5 N1 C2 107.02(10) ? C5 N1 C6 126.95(10) ? C2 N1 C6 126.02(10) ? C4 C5 N1 103.80(11) ? C11 C6 C7 121.18(11) yes C11 C6 N1 119.70(11) ? C7 C6 N1 119.11(11) ? C6 C11 C10 119.04(12) ? C7 C8 C9 120.27(12) ? N3 C2 N1 112.71(11) ? C8 C9 C10 120.04(12) ? N3 C4 C5 113.36(11) ? N3 C4 N2 121.11(11) ? C5 C4 N2 125.48(11) ? C8 C7 C6 119.18(13) ? C9 C10 C11 120.27(14) ? 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 N2 O1 . 1.2216(13) yes N2 O2 . 1.2355(13) yes N2 C4 . 1.4348(16) ? N3 C2 . 1.3106(17) yes N3 C4 . 1.3631(16) yes N1 C5 . 1.3677(15) yes N1 C2 . 1.3703(15) yes N1 C6 . 1.4346(15) yes C5 C4 . 1.3641(17) yes C6 C11 . 1.3833(17) ? C6 C7 . 1.3872(17) ? C11 C10 . 1.3883(17) ? C8 C7 . 1.3837(19) ? C8 C9 . 1.385(2) ? C9 C10 . 1.3855(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 C2 H21 O2 4_456 .953(14) 2.353(14) 3.2466(16) 156.0(11) C5 H51 N3 4_556 .952(15) 2.514(15) 3.4338(18) 162.5(12)