#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2008183.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. G.' 'Billodeaux, D. R.' 'Fronczek, F. 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_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_ _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 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_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_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_ _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