#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/39/2013970.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_2013970 loop_ _publ_author_name 'Kubicki, Maciej' _publ_section_title ; 1-(4-Bromophenyl)-2-methyl-4-nitro-1H-imidazole: bifurcated Br···O halogen--nitro bonds ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o341 _journal_page_last o343 _journal_paper_doi 10.1107/S010827010400650X _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C10 H8 Br N3 O2' _chemical_formula_moiety 'C10 H8 Br N3 O2' _chemical_formula_sum 'C10 H8 Br N3 O2' _chemical_formula_weight 282.10 _chemical_name_systematic ; 1-(4-Bromophenyl)-2-methyl-4-nitro-1H-imidazole ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.1443(5) _cell_length_b 10.4459(8) _cell_length_c 24.1758(19) _cell_measurement_reflns_used 2848 _cell_measurement_temperature 100.0(10) _cell_measurement_theta_max 18 _cell_measurement_theta_min 3 _cell_volume 1046.59(17) _computing_cell_refinement CrysAlisCCD _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlisRED (Oxford Diffraction, 2002)' _computing_molecular_graphics 'Stereochemical Workstation (Siemens, 1989)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100.0(10) _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.871 _diffrn_measurement_device_type 'KUMA KM-4 CCD four-circle' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0962 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 4145 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.15 _diffrn_reflns_theta_min 4.65 _exptl_absorpt_coefficient_mu 3.915 _exptl_absorpt_correction_T_max 0.676 _exptl_absorpt_correction_T_min 0.389 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1989)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.733 _refine_diff_density_min -0.954 _refine_ls_abs_structure_details 'Flack (1983), with x Friedel pairs' _refine_ls_abs_structure_Flack -0.018(15) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 2308 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.101 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0399 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0539P)^2^+0.104P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0862 _refine_ls_wR_factor_ref 0.0973 _reflns_number_gt 1977 _reflns_number_total 2308 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fg1748.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P21 21 21' _cod_database_code 2013970 _cod_database_fobs_code 2013970 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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 0.8048(9) 0.6622(3) 0.67555(12) 0.0137(7) Uani d . 1 . . N C11 0.8719(10) 0.6033(4) 0.62277(13) 0.0124(8) Uani d . 1 . . C C12 1.0078(10) 0.4834(4) 0.62080(15) 0.0153(9) Uani d . 1 . . C H12 1.0584 0.4398 0.6542 0.018 Uiso calc R 1 . . H C13 1.0716(11) 0.4255(4) 0.57008(15) 0.0174(8) Uani d . 1 . . C H13 1.1652 0.3426 0.5685 0.021 Uiso calc R 1 . . H C14 0.9959(10) 0.4914(4) 0.52152(15) 0.0148(9) Uani d . 1 . . C Br14 1.09105(11) 0.41611(4) 0.451856(15) 0.02178(13) Uani d . 1 . . Br C15 0.8543(10) 0.6117(4) 0.52344(15) 0.0185(9) Uani d . 1 . . C H15 0.7996 0.6547 0.4901 0.022 Uiso calc R 1 . . H C16 0.7923(11) 0.6695(4) 0.57435(15) 0.0165(8) Uani d . 1 . . C H16 0.6978 0.7522 0.5761 0.020 Uiso calc R 1 . . H C2 0.9153(11) 0.7801(4) 0.69409(14) 0.0142(8) Uani d . 1 . . C C21 1.1314(11) 0.8655(4) 0.66054(15) 0.0156(8) Uani d . 1 . . C H21A 0.9998 0.9192 0.6361 0.020 Uiso calc R 1 . . H H21B 1.2777 0.8129 0.6382 0.020 Uiso calc R 1 . . H H21C 1.2577 0.9202 0.6854 0.020 Uiso calc R 1 . . H N3 0.8066(8) 0.8049(3) 0.74438(12) 0.0137(7) Uani d . 1 . . N C4 0.6262(10) 0.7002(4) 0.75764(14) 0.0109(7) Uani d . 1 . . C N4 0.4561(9) 0.6931(3) 0.80942(12) 0.0146(7) Uani d . 1 . . N O41 0.4836(7) 0.7810(3) 0.84256(11) 0.0205(7) Uani d . 1 . . O O42 0.2918(8) 0.5960(3) 0.81753(11) 0.0214(7) Uani d . 1 . . O C5 0.6208(11) 0.6093(4) 0.71680(13) 0.0127(8) Uani d . 1 . . C H5 0.5147 0.5287 0.7170 0.015 Uiso calc R 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 0.0142(19) 0.0160(17) 0.0109(13) -0.0005(14) -0.0001(12) -0.0009(12) C11 0.014(2) 0.0130(18) 0.0104(14) -0.0002(17) 0.0015(13) -0.0007(13) C12 0.018(2) 0.0151(19) 0.0126(16) -0.0032(16) -0.0028(14) 0.0015(14) C13 0.018(2) 0.0181(19) 0.0166(16) 0.001(2) 0.0000(16) -0.0049(15) C14 0.017(2) 0.0158(19) 0.0119(16) -0.0001(15) 0.0015(13) -0.0063(14) Br14 0.0243(2) 0.0289(2) 0.01213(17) 0.0013(2) 0.00213(16) -0.00668(16) C15 0.016(2) 0.028(2) 0.0113(16) 0.0005(18) 0.0002(14) 0.0041(15) C16 0.015(2) 0.021(2) 0.0139(18) 0.0037(18) 0.0015(15) 0.0020(16) C2 0.013(2) 0.0187(19) 0.0107(15) 0.007(2) -0.0018(16) 0.0000(13) C21 0.014(2) 0.0153(18) 0.0173(17) 0.0016(18) 0.0034(15) 0.0025(14) N3 0.0129(18) 0.0163(17) 0.0119(14) -0.0008(14) -0.0013(12) 0.0009(12) C4 0.014(2) 0.0087(17) 0.0102(15) 0.0035(17) -0.0009(14) 0.0006(12) N4 0.0156(19) 0.0175(17) 0.0107(14) 0.0021(15) -0.0015(13) 0.0021(12) O41 0.0276(19) 0.0197(15) 0.0142(13) -0.0034(13) 0.0022(11) -0.0065(11) O42 0.0264(17) 0.0202(15) 0.0175(13) -0.0076(15) 0.0044(11) 0.0003(12) C5 0.015(2) 0.0138(18) 0.0096(14) -0.0021(17) -0.0011(14) 0.0019(12) 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' Br Br -0.2901 2.4595 '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 C5 N1 C2 107.8(3) y C5 N1 C11 125.3(3) ? C2 N1 C11 126.9(3) ? C12 C11 C16 121.2(3) ? C12 C11 N1 119.9(3) ? C16 C11 N1 118.9(3) ? C11 C12 C13 120.3(4) ? C11 C12 H12 119.9 ? C13 C12 H12 119.9 ? C12 C13 C14 118.9(4) ? C12 C13 H13 120.5 ? C14 C13 H13 120.5 ? C15 C14 C13 120.9(3) y C15 C14 Br14 119.5(3) y C13 C14 Br14 119.6(3) y C14 C15 C16 119.9(3) ? C14 C15 H15 120.0 ? C16 C15 H15 120.0 ? C15 C16 C11 118.8(4) ? C15 C16 H16 120.6 ? C11 C16 H16 120.6 ? N3 C2 N1 111.0(4) ? N3 C2 C21 125.7(4) ? N1 C2 C21 123.3(3) ? C2 C21 H21A 109.5 ? C2 C21 H21B 109.5 ? H21A C21 H21B 109.5 ? C2 C21 H21C 109.5 ? H21A C21 H21C 109.5 ? H21B C21 H21C 109.5 ? C2 N3 C4 104.3(3) y N3 C4 C5 113.3(3) ? N3 C4 N4 121.0(3) y C5 C4 N4 125.7(4) y O41 N4 O42 124.2(3) y O41 N4 C4 119.0(3) y O42 N4 C4 116.7(3) y C4 C5 N1 103.6(3) ? C4 C5 H5 128.2 ? N1 C5 H5 128.2 ? 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 C5 . 1.372(5) y N1 C2 . 1.389(5) y N1 C11 . 1.443(4) y C11 C12 . 1.375(5) ? C11 C16 . 1.399(5) ? C12 C13 . 1.392(5) ? C12 H12 . 0.9500 ? C13 C14 . 1.396(5) ? C13 H13 . 0.9500 ? C14 C15 . 1.388(6) ? C14 Br14 . 1.900(4) y C15 C16 . 1.395(5) ? C15 H15 . 0.9500 ? C16 H16 . 0.9500 ? C2 N3 . 1.322(5) y C2 C21 . 1.502(6) ? C21 H21A . 0.9800 ? C21 H21B . 0.9800 ? C21 H21C . 0.9800 ? N3 C4 . 1.363(5) y C4 C5 . 1.370(5) ? C4 N4 . 1.439(5) y N4 O41 . 1.224(4) y N4 O42 . 1.237(4) y C5 H5 . 0.9500 ? 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 C12 H12 O41 4_746 0.95 2.52 3.114(5) 121 C21 H21A O42 4_656 0.98 2.48 3.026(5) 115 C21 H21C O42 4_756 0.98 2.62 3.434(5) 141 C5 H5 N3 4_646 0.95 2.85 3.759(5) 161 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 C11 C12 -55.4(6) C2 N1 C11 C12 123.8(5) C5 N1 C11 C16 123.7(4) C2 N1 C11 C16 -57.1(6) C16 C11 C12 C13 0.5(7) N1 C11 C12 C13 179.6(4) C11 C12 C13 C14 0.1(6) C12 C13 C14 C15 -1.1(7) C12 C13 C14 Br14 178.4(3) C13 C14 C15 C16 1.4(6) Br14 C14 C15 C16 -178.1(3) C14 C15 C16 C11 -0.7(6) C12 C11 C16 C15 -0.2(7) N1 C11 C16 C15 -179.3(4) C5 N1 C2 N3 -0.9(5) C11 N1 C2 N3 179.7(4) C5 N1 C2 C21 178.7(4) C11 N1 C2 C21 -0.6(6) N1 C2 N3 C4 0.3(4) C21 C2 N3 C4 -179.3(4) C2 N3 C4 C5 0.5(5) C2 N3 C4 N4 -177.9(4) N3 C4 N4 O41 -2.4(6) C5 C4 N4 O41 179.5(4) N3 C4 N4 O42 178.3(3) C5 C4 N4 O42 0.2(6) N3 C4 C5 N1 -1.0(5) N4 C4 C5 N1 177.2(4) C2 N1 C5 C4 1.1(4) C11 N1 C5 C4 -179.5(4)