#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008183.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_2008183 loop_ _publ_author_name 'Garcia, J. Gabriel' 'Billodeaux, Damon R.' 'Fronczek, Frank R.' _publ_section_title ; Two 3-substituted 5-nitroindoles ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first IUC9900007 _journal_volume 55 _journal_year 1999 _chemical_formula_iupac 'C11 H11 Br N2 O2' _chemical_formula_moiety 'C11 H11 Br N2 O2' _chemical_formula_sum 'C11 H11 Br N2 O2' _chemical_formula_weight 283.1 _chemical_name_systematic ; 3-(3-bromopropyl)-5-nitro-1H-indole ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90 _cell_angle_beta 106.983(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.2326(3) _cell_length_b 16.766(2) _cell_length_c 6.6130(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 43 _cell_measurement_theta_min 33 _cell_volume 554.86(9) _computing_cell_refinement 'CAD-4 Operations Manual' _computing_data_collection 'CAD-4 Operations Manual (Enraf-Nonius, 1977)' _computing_data_reduction 'PROCESS in MolEN (Fair, 1990)' _computing_molecular_graphics ORTEPII_(Johnson,_1976) _computing_publication_material CIF_in_MolEN _computing_structure_refinement LSFM_in_MolEN _computing_structure_solution direct_methods_(SIR;_Burla_et_al.,_1989) _diffrn_ambient_temperature 298 _diffrn_measurement_device Enraf_Nonius_CAD-4 _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source sealed_tube _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 4694 _diffrn_reflns_theta_max 76 _diffrn_standards_decay_% 0.2 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 4.98 _exptl_absorpt_correction_T_max 0.37 _exptl_absorpt_correction_T_min 0.24 _exptl_absorpt_correction_type \y_scans_(North_et_al.,_1968) _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method none _exptl_crystal_description fragment _exptl_crystal_F_000 284 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.71 _refine_diff_density_min -0.63 _refine_ls_abs_structure_details ; Refinement of the antipodal structure under identical circumstances yielded R = 0.040, wR = 0.055, S = 3.056. ; _refine_ls_extinction_coef 1.39E-5(3) _refine_ls_extinction_method isotropic_(Zachariasen,_1963) _refine_ls_goodness_of_fit_obs 1.978 _refine_ls_hydrogen_treatment refined_isotropically _refine_ls_number_parameters 189 _refine_ls_number_reflns 2312 _refine_ls_R_factor_obs 0.025 _refine_ls_shift/esd_max 0.02 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]' _refine_ls_wR_factor_obs 0.036 _reflns_number_observed 2312 _reflns_number_total 2314 _reflns_observed_criterion I>0 _[local]_cod_data_source_file qa0079.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21' _[local]_cod_cif_authors_sg_Hall 'P 2y1' _cod_original_cell_volume 554.90(10) _cod_database_code 2008183 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+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_thermal_displace_type _atom_site_calc_flag Br 0.90568(5) 0 -0.08162(3) 0.06900(10) Uani ? O1 0.4514(3) 0.20520(10) 0.8484(3) 0.0587(7) Uani ? O2 0.3563(3) 0.33020(10) 0.8239(3) 0.0667(8) Uani ? N1 0.9996(3) 0.28670(10) 0.1697(3) 0.0526(8) Uani ? N2 0.4624(3) 0.27160(10) 0.7739(3) 0.0440(7) Uani ? C1 1.1036(4) 0.2110(2) 0.1862(3) 0.0503(9) Uani ? C2 1.0321(3) 0.16870(10) 0.3368(3) 0.0419(8) Uani ? C3 0.8738(3) 0.22160(10) 0.4209(3) 0.0363(7) Uani ? C4 0.8579(4) 0.29550(10) 0.3119(3) 0.0423(8) Uani ? C5 0.7132(4) 0.36030(10) 0.3534(4) 0.0476(9) Uani ? C6 0.5876(4) 0.35220(10) 0.5092(4) 0.0451(9) Uani ? C7 0.6063(3) 0.27950(10) 0.6173(3) 0.0376(8) Uani ? C8 0.7450(3) 0.21450(10) 0.5767(3) 0.0369(7) Uani ? C9 1.1022(4) 0.08380(10) 0.3995(3) 0.0459(9) Uani ? C10 0.8616(4) 0.02730(10) 0.3380(3) 0.0452(8) Uani ? C11 0.6999(4) 0.03110(10) 0.1093(3) 0.0466(9) Uani ? H1N 1.026(6) 0.318(2) 0.070(4) 0.060(8) Uiso ? H1 1.230(6) 0.196(2) 0.107(4) 0.059(8) Uiso ? H5 0.729(8) 0.413(3) 0.277(6) 0.12(2) Uiso ? H6 0.493(5) 0.396(2) 0.542(4) 0.049(6) Uiso ? H8 0.738(5) 0.1660(10) 0.637(4) 0.042(6) Uiso ? H9a 1.187(5) 0.080(2) 0.569(4) 0.056(7) Uiso ? H9b 1.245(5) 0.062(2) 0.326(4) 0.048(6) Uiso ? H10a 0.746(5) 0.040(2) 0.428(4) 0.062(8) Uiso ? H10b 0.918(5) -0.032(2) 0.384(4) 0.059(8) Uiso ? H11a 0.551(4) 0.005(3) 0.083(3) 0.052(7) Uiso ? H11b 0.655(5) 0.085(2) 0.069(4) 0.051(7) Uiso ? 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 Br 0.08990(10) 0.06530(10) 0.05580(10) -0.00620(10) 0.03660(9) -0.01280(10) O1 0.0612(6) 0.0578(9) 0.0572(7) 0.0040(7) 0.0331(6) 0.0076(8) O2 0.0723(7) 0.0603(9) 0.0683(9) 0.0171(7) 0.0348(6) -0.0065(9) N1 0.0551(7) 0.0580(10) 0.0454(8) -0.0157(7) 0.0244(6) 0.0057(8) N2 0.0422(6) 0.0507(8) 0.0397(7) 0.0015(6) 0.0157(6) -0.0045(8) C1 0.0420(7) 0.0650(10) 0.0464(8) -0.0142(8) 0.0227(6) -0.0080(10) C2 0.0343(6) 0.0520(10) 0.0412(8) -0.0070(7) 0.0154(6) -0.0068(8) C3 0.0324(6) 0.0393(9) 0.0377(8) -0.0059(6) 0.0082(6) -0.0018(7) C4 0.0431(7) 0.0463(9) 0.0380(8) -0.0111(7) 0.0117(7) 0.0006(8) C5 0.0549(9) 0.0384(9) 0.0510(10) -0.0079(8) 0.0110(8) 0.0039(9) C6 0.0490(8) 0.0382(9) 0.0490(10) 0.0001(8) 0.0133(7) -0.0015(9) C7 0.0377(7) 0.0410(9) 0.0344(7) -0.0007(6) 0.0084(6) -0.0009(8) C8 0.0369(6) 0.0384(8) 0.0354(7) -0.0031(7) 0.0117(6) -0.0012(8) C9 0.0378(7) 0.0530(10) 0.0480(10) 0.0059(8) 0.0131(7) -0.0058(9) C10 0.0496(7) 0.0437(9) 0.0425(8) 0.0039(7) 0.0228(6) 0.0011(8) C11 0.0459(7) 0.0438(9) 0.0500(10) 0.0002(8) 0.0171(7) -0.0031(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br C11 1.955(2) yes O1 N2 1.227(3) yes O2 N2 1.220(3) yes N1 C1 1.373(3) yes N1 C4 1.365(3) yes N1 H1N 0.88(3) ? N2 C7 1.454(3) ? C1 C2 1.361(3) yes C1 H1 0.99(3) ? C2 C3 1.432(3) ? C2 C9 1.498(3) ? C3 C4 1.424(3) ? C3 C8 1.391(3) ? C4 C5 1.396(3) ? C5 C6 1.382(4) ? C5 H5 1.03(4) ? C6 C7 1.402(3) ? C6 H6 0.95(3) ? C7 C8 1.377(3) ? C8 H8 0.92(3) ? C9 C10 1.533(3) ? C9 H9a 1.08(2) ? C9 H9b 1.07(3) ? C10 C11 1.503(3) ? C10 H10a 0.99(3) ? C10 H10b 1.05(3) ? C11 H11a 0.86(3) ? C11 H11b 0.95(3) ? loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.017 0.009 International_Tables_Vol_IV_Table_2.3.1 H 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N 0.029 0.018 International_Tables_Vol_IV_Table_2.3.1 O 0.047 0.032 International_Tables_Vol_IV_Table_2.3.1 Br -0.767 1.283 International_Tables_Vol_IV_Table_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 5 1 2 4 3 -3 -6 3 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 C1 N1 C4 109.1(2) yes C1 N1 H1N 117(2) ? C4 N1 H1N 133(2) ? O1 N2 O2 122.9(2) yes O1 N2 C7 117.6(2) yes O2 N2 C7 119.5(2) yes N1 C1 C2 110.6(2) yes N1 C1 H1 120.0(10) ? C2 C1 H1 128.0(10) ? C1 C2 C3 106.0(2) ? C1 C2 C9 126.9(2) ? C3 C2 C9 127.1(2) ? C2 C3 C4 107.3(2) ? C2 C3 C8 134.1(2) ? C4 C3 C8 118.7(2) ? N1 C4 C3 106.9(2) ? N1 C4 C5 130.9(2) ? C3 C4 C5 122.2(2) ? C4 C5 C6 118.3(2) ? C4 C5 H5 116(2) ? C6 C5 H5 125(2) ? C5 C6 C7 119.2(2) ? C5 C6 H6 119.0(10) ? C7 C6 H6 121.0(10) ? N2 C7 C6 117.9(2) ? N2 C7 C8 118.6(2) ? C6 C7 C8 123.4(2) ? C3 C8 C7 118.3(2) ? C3 C8 H8 119.0(10) ? C7 C8 H8 122.0(10) ? C2 C9 C10 113.50(10) ? C2 C9 H9a 109.0(10) ? C2 C9 H9b 110.0(10) ? C10 C9 H9a 107.0(10) ? C10 C9 H9b 107.0(10) ? H9a C9 H9b 108.0(10) ? C9 C10 C11 114.7(2) ? C9 C10 H10a 108.0(10) ? C9 C10 H10b 111.0(10) ? C11 C10 H10a 109.0(10) ? C11 C10 H10b 111.0(10) ? H10a C10 H10b 101(2) ? Br C11 C10 112.60(10) yes Br C11 H11a 111(2) ? Br C11 H11b 102.0(10) ? C10 C11 H11a 112.0(10) ? C10 C11 H11b 110.0(10) ? H11a C11 H11b 106(3) ? 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 _geom_torsion_publ_flag C4 N1 C1 C2 0.4(3) ? C1 N1 C4 C3 -0.3(2) ? C1 N1 C4 C5 -178.9(2) ? O1 N2 C7 C6 171.0(2) ? O1 N2 C7 C8 -6.6(3) yes O2 N2 C7 C6 -8.3(3) ? O2 N2 C7 C8 174.2(2) ? N1 C1 C2 C3 -0.3(2) ? N1 C1 C2 C9 179.0(2) ? C1 C2 C3 C4 0.1(3) ? C1 C2 C3 C8 -179.6(2) ? C9 C2 C3 C4 -179.2(2) ? C9 C2 C3 C8 1.1(3) ? C1 C2 C9 C10 -111.5(2) yes C3 C2 C9 C10 67.7(3) ? C2 C3 C4 N1 0.2(2) ? C2 C3 C4 C5 178.9(2) ? C8 C3 C4 N1 179.9(2) ? C8 C3 C4 C5 -1.4(3) ? C2 C3 C8 C7 -179.9(2) ? C4 C3 C8 C7 0.5(3) ? N1 C4 C5 C6 -180.0(4) ? C3 C4 C5 C6 1.6(3) ? C4 C5 C6 C7 -0.9(3) ? C5 C6 C7 N2 -177.4(2) ? C5 C6 C7 C8 0.1(4) ? N2 C7 C8 C3 177.6(2) ? C6 C7 C8 C3 0.2(3) ? C2 C9 C10 C11 52.6(2) yes C9 C10 C11 Br 62.4(2) yes _journal_paper_doi 10.1107/S0108270199099783