# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Richard Grainger' _publ_contact_author_email r.s.grainger@bham.ac.uk _publ_section_title ; Regioselective Dibromination of Methyl Indole-3-Carboxylate and Application in the Synthesis of 5,6-Dibromoindoles ; loop_ _publ_author_name R.Grainger T.Parsons # Attachment 'Indoles.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 818707' #TrackingRef 'Indoles.cif' # UK National Crystallography Service Code: 2009src1024 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Methyl 5,6-dibromo-1H-indole-3-carboxylate ; _chemical_name_common 'Methyl 5,6-dibromo-1H-indole-3-carboxylate' _chemical_melting_point ? _chemical_formula_moiety 'C10 H7 Br2 N O2' _chemical_formula_sum 'C10 H7 Br2 N O2' _chemical_formula_weight 332.99 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1280(4) _cell_length_b 7.3609(4) _cell_length_c 10.9238(6) _cell_angle_alpha 90.492(3) _cell_angle_beta 98.609(3) _cell_angle_gamma 112.463(3) _cell_volume 522.34(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 27233 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Slab _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.117 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 7.736 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3708 _exptl_absorpt_correction_T_max 0.7472 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 9049 reflections reduced R(int) from 0.0608 to 0.0298 Ratio of minimum to maximum apparent transmission: 0.658362 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9706 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2390 _reflns_number_gt 2089 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ; SIR92, (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori & Camalli, 1994) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K, & Puschmann, H., 2009) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0115P)^2^+1.1724P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2390 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0598 _refine_ls_wR_factor_gt 0.0559 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7977(4) 0.3409(4) 0.6944(3) 0.0166(6) Uani 1 1 d . . . C2 C 0.6172(5) 0.3560(4) 0.7229(3) 0.0183(6) Uani 1 1 d . . . C3 C 0.4439(5) 0.3144(4) 0.6334(3) 0.0186(6) Uani 1 1 d . . . H3 H 0.3220 0.3239 0.6525 0.022 Uiso 1 1 calc R . . C4 C 0.4573(4) 0.2580(4) 0.5139(3) 0.0160(6) Uani 1 1 d . . . C5 C 0.6373(4) 0.2454(4) 0.4833(3) 0.0169(6) Uani 1 1 d . . . C6 C 0.8104(4) 0.2884(4) 0.5754(3) 0.0179(6) Uani 1 1 d . . . H6 H 0.9334 0.2817 0.5564 0.021 Uiso 1 1 calc R . . C7 C 0.3919(5) 0.1631(4) 0.3119(3) 0.0182(6) Uani 1 1 d . . . H7 H 0.3210 0.1240 0.2292 0.022 Uiso 1 1 calc R . . C8 C 0.5929(4) 0.1847(4) 0.3527(3) 0.0164(6) Uani 1 1 d . . . C9 C 0.7321(4) 0.1473(4) 0.2812(3) 0.0176(6) Uani 1 1 d . . . C10 C 0.7825(5) 0.0630(5) 0.0830(3) 0.0246(7) Uani 1 1 d . . . H10A H 0.9058 0.1836 0.0846 0.037 Uiso 1 1 calc R . . H10B H 0.7088 0.0255 -0.0024 0.037 Uiso 1 1 calc R . . H10C H 0.8226 -0.0435 0.1144 0.037 Uiso 1 1 calc R . . N1 N 0.3110(4) 0.2061(4) 0.4076(2) 0.0179(5) Uani 1 1 d . . . H1 H 0.1849 0.2017 0.4026 0.022 Uiso 1 1 calc R . . O1 O 0.9028(3) 0.1568(3) 0.32424(19) 0.0226(5) Uani 1 1 d . . . O2 O 0.6495(3) 0.0974(3) 0.16055(18) 0.0203(4) Uani 1 1 d . . . Br1 Br 1.02871(5) 0.38748(5) 0.81913(3) 0.02214(9) Uani 1 1 d . . . Br2 Br 0.60632(5) 0.43601(5) 0.88598(3) 0.02448(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0146(14) 0.0187(14) 0.0155(13) 0.0000(11) -0.0019(11) 0.0069(11) C2 0.0232(15) 0.0164(14) 0.0151(13) 0.0001(11) 0.0044(11) 0.0071(12) C3 0.0184(15) 0.0174(14) 0.0213(14) 0.0012(12) 0.0034(12) 0.0082(12) C4 0.0144(14) 0.0155(13) 0.0173(13) 0.0016(11) 0.0012(11) 0.0055(11) C5 0.0151(14) 0.0137(13) 0.0204(14) -0.0018(11) 0.0054(11) 0.0032(11) C6 0.0164(14) 0.0183(14) 0.0180(14) 0.0019(11) 0.0040(11) 0.0052(12) C7 0.0206(15) 0.0183(14) 0.0153(13) -0.0004(11) 0.0006(11) 0.0079(12) C8 0.0173(14) 0.0159(14) 0.0145(13) 0.0008(11) 0.0009(11) 0.0055(11) C9 0.0171(15) 0.0153(14) 0.0167(14) 0.0020(11) 0.0014(11) 0.0028(11) C10 0.0238(17) 0.0322(17) 0.0197(15) -0.0024(13) 0.0062(13) 0.0122(14) N1 0.0133(12) 0.0206(13) 0.0197(12) 0.0006(10) 0.0006(10) 0.0073(10) O1 0.0163(11) 0.0336(12) 0.0187(10) 0.0010(9) 0.0004(8) 0.0116(9) O2 0.0189(11) 0.0285(12) 0.0141(10) -0.0017(8) 0.0010(8) 0.0106(9) Br1 0.01945(16) 0.02891(18) 0.01690(15) -0.00021(12) -0.00146(11) 0.00977(13) Br2 0.02505(18) 0.03249(19) 0.01727(16) -0.00368(12) 0.00320(12) 0.01287(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.379(4) . ? C1 C2 1.411(4) . ? C1 Br1 1.891(3) . ? C2 C3 1.386(4) . ? C2 Br2 1.894(3) . ? C3 C4 1.394(4) . ? C3 H3 0.9500 . ? C4 N1 1.382(4) . ? C4 C5 1.409(4) . ? C5 C6 1.399(4) . ? C5 C8 1.443(4) . ? C6 H6 0.9500 . ? C7 N1 1.356(4) . ? C7 C8 1.382(4) . ? C7 H7 0.9500 . ? C8 C9 1.451(4) . ? C9 O1 1.213(3) . ? C9 O2 1.347(3) . ? C10 O2 1.449(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N1 H1 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.2(3) . . ? C6 C1 Br1 117.7(2) . . ? C2 C1 Br1 121.0(2) . . ? C3 C2 C1 121.6(3) . . ? C3 C2 Br2 117.9(2) . . ? C1 C2 Br2 120.5(2) . . ? C2 C3 C4 116.6(3) . . ? C2 C3 H3 121.7 . . ? C4 C3 H3 121.7 . . ? N1 C4 C3 129.6(3) . . ? N1 C4 C5 107.8(2) . . ? C3 C4 C5 122.6(3) . . ? C6 C5 C4 119.7(3) . . ? C6 C5 C8 133.9(3) . . ? C4 C5 C8 106.4(3) . . ? C1 C6 C5 118.3(3) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? N1 C7 C8 109.9(3) . . ? N1 C7 H7 125.1 . . ? C8 C7 H7 125.1 . . ? C7 C8 C5 106.5(3) . . ? C7 C8 C9 127.6(3) . . ? C5 C8 C9 125.9(3) . . ? O1 C9 O2 123.1(3) . . ? O1 C9 C8 124.5(3) . . ? O2 C9 C8 112.4(2) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 N1 C4 109.4(2) . . ? C7 N1 H1 125.3 . . ? C4 N1 H1 125.3 . . ? C9 O2 C10 115.3(2) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.5(4) . . . . ? Br1 C1 C2 C3 -177.3(2) . . . . ? C6 C1 C2 Br2 -178.1(2) . . . . ? Br1 C1 C2 Br2 3.1(3) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? Br2 C2 C3 C4 179.3(2) . . . . ? C2 C3 C4 N1 179.2(3) . . . . ? C2 C3 C4 C5 -0.8(4) . . . . ? N1 C4 C5 C6 -179.3(3) . . . . ? C3 C4 C5 C6 0.7(4) . . . . ? N1 C4 C5 C8 0.5(3) . . . . ? C3 C4 C5 C8 -179.6(3) . . . . ? C2 C1 C6 C5 -1.6(4) . . . . ? Br1 C1 C6 C5 177.3(2) . . . . ? C4 C5 C6 C1 0.5(4) . . . . ? C8 C5 C6 C1 -179.1(3) . . . . ? N1 C7 C8 C5 0.0(3) . . . . ? N1 C7 C8 C9 177.9(3) . . . . ? C6 C5 C8 C7 179.3(3) . . . . ? C4 C5 C8 C7 -0.3(3) . . . . ? C6 C5 C8 C9 1.4(5) . . . . ? C4 C5 C8 C9 -178.2(3) . . . . ? C7 C8 C9 O1 -175.0(3) . . . . ? C5 C8 C9 O1 2.4(5) . . . . ? C7 C8 C9 O2 4.1(4) . . . . ? C5 C8 C9 O2 -178.5(3) . . . . ? C8 C7 N1 C4 0.2(3) . . . . ? C3 C4 N1 C7 179.6(3) . . . . ? C5 C4 N1 C7 -0.4(3) . . . . ? O1 C9 O2 C10 -2.4(4) . . . . ? C8 C9 O2 C10 178.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.687 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.098 #============================================================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 818708' #TrackingRef 'Indoles.cif' # UK National Crystallography Service Code: 2009src1029 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-tert-Butyl-3-methyl 5,6-dibromo-1H-indole-1,3-dicarboxylate ; _chemical_name_common '1-tert-Butyl-3-methyl 5,6-dibromo-1H-indole-1,3-dicarboxylate' _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 Br2 N O4' _chemical_formula_sum 'C15 H15 Br2 N O4' _chemical_formula_weight 433.10 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0596(3) _cell_length_b 10.6930(4) _cell_length_c 11.4729(4) _cell_angle_alpha 96.062(2) _cell_angle_beta 94.194(2) _cell_angle_gamma 106.037(2) _cell_volume 822.95(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 15929 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 4.941 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3835 _exptl_absorpt_correction_T_max 0.9076 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission from SADABS: 0.5659 and 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17723 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3762 _reflns_number_gt 2966 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ; SIR92, (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori & Camalli, 1994) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K, & Puschmann, H., 2009) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0169P)^2^+1.0488P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3762 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1427(5) 0.0414(3) 0.3110(3) 0.0207(7) Uani 1 1 d . . . C2 C 0.1996(5) 0.1703(3) 0.3692(3) 0.0214(7) Uani 1 1 d . . . C3 C 0.2731(5) 0.1981(3) 0.4869(3) 0.0193(7) Uani 1 1 d . . . H3 H 0.3090 0.2851 0.5268 0.023 Uiso 1 1 calc R . . C4 C 0.2925(4) 0.0938(3) 0.5445(3) 0.0156(6) Uani 1 1 d . . . C5 C 0.2381(4) -0.0363(3) 0.4865(3) 0.0163(6) Uani 1 1 d . . . C6 C 0.1613(4) -0.0625(3) 0.3688(3) 0.0191(7) Uani 1 1 d . . . H6 H 0.1225 -0.1496 0.3289 0.023 Uiso 1 1 calc R . . C7 C 0.3582(4) -0.0377(3) 0.6757(3) 0.0173(6) Uani 1 1 d . . . H7 H 0.3993 -0.0656 0.7468 0.021 Uiso 1 1 calc R . . C8 C 0.2822(4) -0.1175(3) 0.5723(3) 0.0159(6) Uani 1 1 d . . . C9 C 0.2508(4) -0.2601(3) 0.5485(3) 0.0198(7) Uani 1 1 d . . . C10 C 0.2740(6) -0.4504(3) 0.6277(3) 0.0308(8) Uani 1 1 d . . . H10A H 0.1326 -0.4949 0.6064 0.046 Uiso 1 1 calc R . . H10B H 0.3189 -0.4779 0.7011 0.046 Uiso 1 1 calc R . . H10C H 0.3493 -0.4738 0.5646 0.046 Uiso 1 1 calc R . . C11 C 0.4316(5) 0.2010(3) 0.7482(3) 0.0202(7) Uani 1 1 d . . . C12 C 0.5783(5) 0.2667(3) 0.9525(3) 0.0242(7) Uani 1 1 d . . . C13 C 0.6346(7) 0.1852(4) 1.0421(3) 0.0410(10) Uani 1 1 d . . . H13A H 0.5164 0.1166 1.0553 0.062 Uiso 1 1 calc R . . H13B H 0.6904 0.2418 1.1166 0.062 Uiso 1 1 calc R . . H13C H 0.7332 0.1446 1.0125 0.062 Uiso 1 1 calc R . . C14 C 0.7564(5) 0.3713(4) 0.9257(3) 0.0360(9) Uani 1 1 d . . . H14A H 0.8527 0.3298 0.8939 0.054 Uiso 1 1 calc R . . H14B H 0.8175 0.4300 0.9982 0.054 Uiso 1 1 calc R . . H14C H 0.7145 0.4218 0.8675 0.054 Uiso 1 1 calc R . . C15 C 0.4109(6) 0.3193(3) 0.9906(3) 0.0302(8) Uani 1 1 d . . . H15A H 0.3790 0.3741 0.9332 0.045 Uiso 1 1 calc R . . H15B H 0.4516 0.3719 1.0683 0.045 Uiso 1 1 calc R . . H15C H 0.2937 0.2457 0.9951 0.045 Uiso 1 1 calc R . . N1 N 0.3660(4) 0.0908(2) 0.6605(2) 0.0165(5) Uani 1 1 d . . . O1 O 0.1842(4) -0.3245(2) 0.4538(2) 0.0292(6) Uani 1 1 d . . . O2 O 0.3057(3) -0.3096(2) 0.64408(19) 0.0220(5) Uani 1 1 d . . . O3 O 0.4179(4) 0.3067(2) 0.73086(19) 0.0281(6) Uani 1 1 d . . . O4 O 0.5046(3) 0.1660(2) 0.84552(18) 0.0212(5) Uani 1 1 d . . . Br1 Br 0.03601(5) 0.00300(4) 0.15018(3) 0.02946(11) Uani 1 1 d . . . Br2 Br 0.17614(5) 0.31353(4) 0.29058(3) 0.02811(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0157(16) 0.036(2) 0.0102(14) 0.0050(13) -0.0013(12) 0.0069(14) C2 0.0164(16) 0.0278(19) 0.0234(17) 0.0104(14) 0.0056(13) 0.0088(14) C3 0.0176(16) 0.0225(17) 0.0195(16) 0.0049(13) 0.0043(13) 0.0072(13) C4 0.0117(15) 0.0206(16) 0.0150(15) 0.0051(12) 0.0038(12) 0.0041(12) C5 0.0108(14) 0.0208(16) 0.0174(15) 0.0026(13) 0.0036(12) 0.0042(12) C6 0.0122(15) 0.0261(18) 0.0178(16) 0.0005(13) 0.0028(12) 0.0039(13) C7 0.0167(16) 0.0189(16) 0.0177(15) 0.0056(13) 0.0036(12) 0.0060(13) C8 0.0129(15) 0.0184(16) 0.0166(15) 0.0030(12) 0.0016(12) 0.0045(12) C9 0.0132(15) 0.0207(17) 0.0247(17) 0.0027(14) 0.0046(13) 0.0030(13) C10 0.034(2) 0.0155(17) 0.042(2) 0.0057(15) -0.0030(17) 0.0070(15) C11 0.0207(17) 0.0220(18) 0.0184(16) 0.0013(13) 0.0041(13) 0.0070(14) C12 0.0318(19) 0.0200(17) 0.0167(16) -0.0039(13) -0.0050(14) 0.0050(15) C13 0.068(3) 0.031(2) 0.0222(19) -0.0028(16) -0.0161(19) 0.018(2) C14 0.029(2) 0.035(2) 0.036(2) -0.0061(17) -0.0013(17) 0.0003(17) C15 0.041(2) 0.0232(19) 0.0233(18) -0.0043(14) 0.0040(16) 0.0065(16) N1 0.0187(13) 0.0150(13) 0.0156(13) 0.0024(10) 0.0004(11) 0.0045(11) O1 0.0372(15) 0.0210(13) 0.0242(13) -0.0047(10) -0.0047(11) 0.0046(11) O2 0.0256(12) 0.0137(11) 0.0261(12) 0.0030(9) -0.0009(10) 0.0053(9) O3 0.0465(16) 0.0174(12) 0.0217(12) 0.0021(10) -0.0013(11) 0.0125(11) O4 0.0294(13) 0.0182(12) 0.0154(11) -0.0010(9) -0.0046(9) 0.0086(10) Br1 0.0274(2) 0.0450(2) 0.01479(17) 0.00584(15) -0.00116(14) 0.00856(16) Br2 0.0287(2) 0.0357(2) 0.02587(19) 0.01645(15) 0.00444(15) 0.01390(16) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.383(4) . ? C1 C2 1.403(5) . ? C1 Br1 1.898(3) . ? C2 C3 1.381(4) . ? C2 Br2 1.896(3) . ? C3 C4 1.388(4) . ? C3 H3 0.9500 . ? C4 N1 1.399(4) . ? C4 C5 1.413(4) . ? C5 C6 1.387(4) . ? C5 C8 1.451(4) . ? C6 H6 0.9500 . ? C7 C8 1.365(4) . ? C7 N1 1.391(4) . ? C7 H7 0.9500 . ? C8 C9 1.471(4) . ? C9 O1 1.210(4) . ? C9 O2 1.344(4) . ? C10 O2 1.450(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O3 1.197(4) . ? C11 O4 1.327(4) . ? C11 N1 1.413(4) . ? C12 O4 1.501(4) . ? C12 C14 1.509(5) . ? C12 C15 1.515(5) . ? C12 C13 1.516(5) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.2(3) . . ? C6 C1 Br1 117.6(2) . . ? C2 C1 Br1 121.2(2) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 Br2 117.1(2) . . ? C1 C2 Br2 121.6(2) . . ? C2 C3 C4 117.4(3) . . ? C2 C3 H3 121.3 . . ? C4 C3 H3 121.3 . . ? C3 C4 N1 130.8(3) . . ? C3 C4 C5 121.9(3) . . ? N1 C4 C5 107.4(3) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 C8 133.5(3) . . ? C4 C5 C8 106.6(3) . . ? C1 C6 C5 118.4(3) . . ? C1 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C8 C7 N1 109.2(3) . . ? C8 C7 H7 125.4 . . ? N1 C7 H7 125.4 . . ? C7 C8 C5 107.7(3) . . ? C7 C8 C9 127.4(3) . . ? C5 C8 C9 124.8(3) . . ? O1 C9 O2 124.3(3) . . ? O1 C9 C8 123.8(3) . . ? O2 C9 C8 111.9(3) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 O4 128.7(3) . . ? O3 C11 N1 121.8(3) . . ? O4 C11 N1 109.5(3) . . ? O4 C12 C14 108.9(3) . . ? O4 C12 C15 109.7(3) . . ? C14 C12 C15 113.8(3) . . ? O4 C12 C13 101.6(2) . . ? C14 C12 C13 111.7(3) . . ? C15 C12 C13 110.4(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 N1 C4 109.1(2) . . ? C7 N1 C11 125.9(3) . . ? C4 N1 C11 125.0(3) . . ? C9 O2 C10 114.9(2) . . ? C11 O4 C12 119.0(2) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.1(5) . . . . ? Br1 C1 C2 C3 178.5(2) . . . . ? C6 C1 C2 Br2 179.6(2) . . . . ? Br1 C1 C2 Br2 -0.7(4) . . . . ? C1 C2 C3 C4 1.4(4) . . . . ? Br2 C2 C3 C4 -179.4(2) . . . . ? C2 C3 C4 N1 178.0(3) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? N1 C4 C5 C6 -179.4(3) . . . . ? C3 C4 C5 C8 178.8(3) . . . . ? N1 C4 C5 C8 -0.1(3) . . . . ? C2 C1 C6 C5 0.0(5) . . . . ? Br1 C1 C6 C5 -179.7(2) . . . . ? C4 C5 C6 C1 0.8(4) . . . . ? C8 C5 C6 C1 -178.3(3) . . . . ? N1 C7 C8 C5 -0.3(3) . . . . ? N1 C7 C8 C9 179.1(3) . . . . ? C6 C5 C8 C7 179.5(3) . . . . ? C4 C5 C8 C7 0.2(3) . . . . ? C6 C5 C8 C9 0.1(5) . . . . ? C4 C5 C8 C9 -179.2(3) . . . . ? C7 C8 C9 O1 -179.2(3) . . . . ? C5 C8 C9 O1 0.0(5) . . . . ? C7 C8 C9 O2 0.5(4) . . . . ? C5 C8 C9 O2 179.7(3) . . . . ? C8 C7 N1 C4 0.3(3) . . . . ? C8 C7 N1 C11 178.5(3) . . . . ? C3 C4 N1 C7 -178.8(3) . . . . ? C5 C4 N1 C7 -0.1(3) . . . . ? C3 C4 N1 C11 2.9(5) . . . . ? C5 C4 N1 C11 -178.4(3) . . . . ? O3 C11 N1 C7 -173.4(3) . . . . ? O4 C11 N1 C7 6.3(4) . . . . ? O3 C11 N1 C4 4.5(5) . . . . ? O4 C11 N1 C4 -175.7(3) . . . . ? O1 C9 O2 C10 -1.8(4) . . . . ? C8 C9 O2 C10 178.5(3) . . . . ? O3 C11 O4 C12 1.5(5) . . . . ? N1 C11 O4 C12 -178.2(2) . . . . ? C14 C12 O4 C11 -65.3(4) . . . . ? C15 C12 O4 C11 59.9(4) . . . . ? C13 C12 O4 C11 176.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.466 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.125 #============================================================================== data_7 _database_code_depnum_ccdc_archive 'CCDC 818709' #TrackingRef 'Indoles.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,6-Dibromo-1H-indole ; _chemical_name_common 5,6-Dibromo-1H-indole _chemical_melting_point ? _chemical_formula_moiety 'C8 H5 Br2 N' _chemical_formula_sum 'C8 H5 Br2 N' _chemical_formula_weight 274.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0874(6) _cell_length_b 7.5403(4) _cell_length_c 18.8720(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1577.74(15) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6615 _cell_measurement_theta_min 4.626 _cell_measurement_theta_max 70.804 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 12.421 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.1286 _exptl_absorpt_correction_T_max 0.1902 _exptl_absorpt_process_details 'SADABS V2.07 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 14025 reflections reduced R(int) from 0.0925 to 0.0317 Ratio of minimum to maximum apparent transmission: 0.648072 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 6000' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14874 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0153 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 7.48 _diffrn_reflns_theta_max 70.03 _reflns_number_total 1491 _reflns_number_gt 1483 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART V5.626 (Bruker, 1997)' _computing_cell_refinement 'SAINT V6.28A (Bruker, 1997)' _computing_data_reduction 'SAINT V6.28A (Bruker, 1997)' _computing_structure_solution ; Sir2004 (Burla, Caliandro, Camalli, Carrozzini, Cascarano, De Caro, Giacovazzo, Polidori, & Spagna, 2005) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K, & Puschmann, H., 2009) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+3.2618P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1491 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0281 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.197 _refine_ls_restrained_S_all 1.197 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0619(3) 0.2157(4) 0.14167(16) 0.0136(6) Uani 1 1 d . . . C2 C 0.1746(3) 0.1318(4) 0.13997(15) 0.0126(6) Uani 1 1 d . . . C3 C 0.2373(3) 0.0940(4) 0.20101(17) 0.0142(6) Uani 1 1 d . . . H3 H 0.3134 0.0362 0.1996 0.017 Uiso 1 1 calc R . . C4 C 0.1848(3) 0.1439(4) 0.26505(15) 0.0127(6) Uani 1 1 d . . . C5 C 0.0725(3) 0.2333(4) 0.26796(16) 0.0141(6) Uani 1 1 d . . . C6 C 0.0111(3) 0.2696(4) 0.20512(17) 0.0138(6) Uani 1 1 d . . . H6 H -0.0640 0.3302 0.2058 0.017 Uiso 1 1 calc R . . C7 C 0.0482(3) 0.2646(4) 0.34148(18) 0.0190(7) Uani 1 1 d . . . H7 H -0.0202 0.3235 0.3607 0.023 Uiso 1 1 calc R . . C8 C 0.1420(3) 0.1937(4) 0.37849(16) 0.0217(7) Uani 1 1 d . . . H8 H 0.1492 0.1950 0.4287 0.026 Uiso 1 1 calc R . . N1 N 0.2245(2) 0.1205(4) 0.33332(14) 0.0196(6) Uani 1 1 d . . . H1 H 0.2918 0.0672 0.3459 0.024 Uiso 1 1 calc R . . Br1 Br -0.02617(3) 0.25563(5) 0.057327(16) 0.01970(15) Uani 1 1 d . . . Br2 Br 0.24547(3) 0.06105(4) 0.053205(16) 0.01896(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0139(14) 0.0138(13) 0.0132(14) 0.0021(11) -0.0020(12) -0.0011(11) C2 0.0154(13) 0.0080(13) 0.0142(13) -0.0010(11) 0.0023(11) -0.0017(10) C3 0.0114(13) 0.0125(13) 0.0187(15) 0.0012(12) 0.0005(11) 0.0002(11) C4 0.0143(13) 0.0089(13) 0.0148(14) 0.0017(10) -0.0011(11) -0.0023(10) C5 0.0154(15) 0.0112(13) 0.0158(15) -0.0001(10) 0.0037(12) -0.0039(11) C6 0.0134(14) 0.0080(13) 0.0201(15) -0.0012(11) 0.0008(12) 0.0008(10) C7 0.0208(15) 0.0168(15) 0.0195(17) -0.0037(12) 0.0064(13) -0.0027(12) C8 0.0282(17) 0.0265(17) 0.0104(14) 0.0005(12) -0.0014(12) -0.0060(14) N1 0.0205(13) 0.0229(14) 0.0154(13) 0.0044(11) -0.0034(10) -0.0002(12) Br1 0.0173(2) 0.0274(2) 0.0144(2) 0.00133(11) -0.00493(11) 0.00142(13) Br2 0.0255(2) 0.0164(2) 0.0150(2) -0.00212(11) 0.00488(12) 0.00475(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.384(4) . ? C1 C2 1.401(4) . ? C1 Br1 1.891(3) . ? C2 C3 1.375(4) . ? C2 Br2 1.893(3) . ? C3 C4 1.393(4) . ? C3 H3 0.9500 . ? C4 N1 1.373(4) . ? C4 C5 1.417(4) . ? C5 C6 1.395(4) . ? C5 C7 1.433(5) . ? C6 H6 0.9500 . ? C7 C8 1.363(5) . ? C7 H7 0.9500 . ? C8 N1 1.367(4) . ? C8 H8 0.9500 . ? N1 H1 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.0(3) . . ? C6 C1 Br1 118.1(2) . . ? C2 C1 Br1 120.9(2) . . ? C3 C2 C1 121.7(3) . . ? C3 C2 Br2 117.2(2) . . ? C1 C2 Br2 121.1(2) . . ? C2 C3 C4 117.3(3) . . ? C2 C3 H3 121.3 . . ? C4 C3 H3 121.3 . . ? N1 C4 C3 130.2(3) . . ? N1 C4 C5 107.9(3) . . ? C3 C4 C5 122.0(3) . . ? C6 C5 C4 119.3(3) . . ? C6 C5 C7 134.4(3) . . ? C4 C5 C7 106.3(3) . . ? C1 C6 C5 118.6(3) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C8 C7 C5 106.7(3) . . ? C8 C7 H7 126.6 . . ? C5 C7 H7 126.6 . . ? C7 C8 N1 110.5(3) . . ? C7 C8 H8 124.8 . . ? N1 C8 H8 124.8 . . ? C8 N1 C4 108.6(3) . . ? C8 N1 H1 125.7 . . ? C4 N1 H1 125.7 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.3(4) . . . . ? Br1 C1 C2 C3 -176.8(2) . . . . ? C6 C1 C2 Br2 -179.1(2) . . . . ? Br1 C1 C2 Br2 1.8(3) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? Br2 C2 C3 C4 -179.2(2) . . . . ? C2 C3 C4 N1 178.4(3) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? N1 C4 C5 C6 -178.5(3) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? N1 C4 C5 C7 1.0(3) . . . . ? C3 C4 C5 C7 -179.3(3) . . . . ? C2 C1 C6 C5 -2.2(4) . . . . ? Br1 C1 C6 C5 177.0(2) . . . . ? C4 C5 C6 C1 0.5(4) . . . . ? C7 C5 C6 C1 -178.8(3) . . . . ? C6 C5 C7 C8 178.5(3) . . . . ? C4 C5 C7 C8 -0.8(3) . . . . ? C5 C7 C8 N1 0.4(4) . . . . ? C7 C8 N1 C4 0.3(4) . . . . ? C3 C4 N1 C8 179.5(3) . . . . ? C5 C4 N1 C8 -0.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 70.03 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.483 _refine_diff_density_min -0.938 _refine_diff_density_rms 0.144 #============================================================================== data_10 _database_code_depnum_ccdc_archive 'CCDC 818710' #TrackingRef 'Indoles.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5,6-Tribromo-1H-indole ; _chemical_name_common 3,5,6-Tribromo-1H-indole _chemical_melting_point ? _chemical_formula_moiety 'C8 H4 Br3 N' _chemical_formula_sum 'C8 H4 Br3 N' _chemical_formula_weight 353.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8688(4) _cell_length_b 6.0886(3) _cell_length_c 16.8852(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.443(3) _cell_angle_gamma 90.00 _cell_volume 911.49(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8290 _cell_measurement_theta_min 4.989 _cell_measurement_theta_max 70.721 _exptl_crystal_description Shard _exptl_crystal_colour 'Pale Brown' _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 15.928 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.0669 _exptl_absorpt_correction_T_max 0.3622 _exptl_absorpt_process_details 'SADABS V2.07 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 8542 reflections reduced R(int) from 0.1450 to 0.0409 Ratio of minimum to maximum apparent transmission: 0.511588 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 6000' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8715 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 7.15 _diffrn_reflns_theta_max 66.59 _reflns_number_total 1603 _reflns_number_gt 1589 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART V5.626 (Bruker, 1997)' _computing_cell_refinement 'SAINT V6.28A (Bruker, 1997)' _computing_data_reduction 'SAINT V6.28A (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K, & Puschmann, H., 2009) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+1.4586P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00111(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1603 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0251 _refine_ls_wR_factor_ref 0.0666 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1766(3) 0.3985(5) 0.63804(17) 0.0177(6) Uani 1 1 d . . . C2 C -0.1704(3) 0.5942(5) 0.68279(17) 0.0178(6) Uani 1 1 d . . . C3 C -0.0419(4) 0.7202(5) 0.68748(19) 0.0200(6) Uani 1 1 d . . . H3 H -0.0384 0.8524 0.7174 0.024 Uiso 1 1 calc R . . C4 C 0.0825(3) 0.6471(5) 0.64698(18) 0.0186(6) Uani 1 1 d . . . C5 C 0.0783(3) 0.4503(5) 0.60251(17) 0.0169(6) Uani 1 1 d . . . C6 C -0.0525(3) 0.3256(5) 0.59801(18) 0.0165(6) Uani 1 1 d . . . H6 H -0.0565 0.1933 0.5682 0.020 Uiso 1 1 calc R . . C7 C 0.2243(3) 0.4297(5) 0.56961(17) 0.0178(6) Uani 1 1 d . . . C8 C 0.3096(3) 0.6039(6) 0.59330(18) 0.0223(7) Uani 1 1 d . . . H8 H 0.4113 0.6303 0.5796 0.027 Uiso 1 1 calc R . . N1 N 0.2239(3) 0.7354(5) 0.64034(17) 0.0232(6) Uani 1 1 d . . . H1 H 0.2549 0.8582 0.6629 0.028 Uiso 1 1 calc R . . Br1 Br -0.35715(4) 0.23772(6) 0.62745(2) 0.02592(15) Uani 1 1 d . . . Br2 Br -0.34051(4) 0.69152(5) 0.738781(19) 0.02233(15) Uani 1 1 d . . . Br3 Br 0.28548(3) 0.19530(5) 0.506332(19) 0.02110(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0146(14) 0.0179(16) 0.0207(15) 0.0036(12) 0.0012(11) 0.0013(11) C2 0.0156(14) 0.0181(15) 0.0196(14) 0.0009(12) 0.0008(11) 0.0056(12) C3 0.0237(16) 0.0166(15) 0.0197(15) -0.0010(12) -0.0004(12) -0.0002(12) C4 0.0193(15) 0.0182(15) 0.0183(14) 0.0011(12) -0.0014(11) -0.0026(12) C5 0.0151(14) 0.0186(15) 0.0170(13) 0.0014(12) -0.0023(11) -0.0006(12) C6 0.0157(15) 0.0158(14) 0.0179(14) -0.0021(11) 0.0003(11) -0.0007(11) C7 0.0137(13) 0.0187(15) 0.0209(14) 0.0022(12) 0.0014(11) 0.0014(12) C8 0.0163(14) 0.0256(17) 0.0252(16) 0.0027(13) 0.0034(12) -0.0032(13) N1 0.0185(14) 0.0211(14) 0.0300(15) -0.0026(11) 0.0015(11) -0.0085(11) Br1 0.0138(2) 0.0246(2) 0.0397(2) -0.00791(14) 0.00785(15) -0.00547(12) Br2 0.0196(2) 0.0230(2) 0.0247(2) -0.00140(12) 0.00469(14) 0.00665(12) Br3 0.0159(2) 0.0231(2) 0.0244(2) -0.00186(12) 0.00344(14) 0.00095(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.379(4) . ? C1 C2 1.411(5) . ? C1 Br1 1.882(3) . ? C2 C3 1.375(5) . ? C2 Br2 1.896(3) . ? C3 C4 1.386(5) . ? C3 H3 0.9500 . ? C4 N1 1.371(4) . ? C4 C5 1.414(4) . ? C5 C6 1.387(4) . ? C5 C7 1.427(4) . ? C6 H6 0.9500 . ? C7 C8 1.357(5) . ? C7 Br3 1.871(3) . ? C8 N1 1.371(4) . ? C8 H8 0.9500 . ? N1 H1 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.9(3) . . ? C6 C1 Br1 118.3(2) . . ? C2 C1 Br1 120.8(2) . . ? C3 C2 C1 121.6(3) . . ? C3 C2 Br2 117.8(2) . . ? C1 C2 Br2 120.7(2) . . ? C2 C3 C4 117.5(3) . . ? C2 C3 H3 121.3 . . ? C4 C3 H3 121.3 . . ? N1 C4 C3 130.9(3) . . ? N1 C4 C5 107.5(3) . . ? C3 C4 C5 121.6(3) . . ? C6 C5 C4 120.3(3) . . ? C6 C5 C7 134.1(3) . . ? C4 C5 C7 105.6(3) . . ? C1 C6 C5 118.2(3) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? C8 C7 C5 108.7(3) . . ? C8 C7 Br3 126.6(2) . . ? C5 C7 Br3 124.6(2) . . ? C7 C8 N1 108.3(3) . . ? C7 C8 H8 125.9 . . ? N1 C8 H8 125.9 . . ? C4 N1 C8 109.9(3) . . ? C4 N1 H1 125.1 . . ? C8 N1 H1 125.1 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.8(5) . . . . ? Br1 C1 C2 C3 -176.3(2) . . . . ? C6 C1 C2 Br2 -179.2(2) . . . . ? Br1 C1 C2 Br2 3.8(3) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? Br2 C2 C3 C4 179.4(2) . . . . ? C2 C3 C4 N1 179.8(3) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? N1 C4 C5 C6 -179.5(3) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? N1 C4 C5 C7 -0.2(3) . . . . ? C3 C4 C5 C7 179.8(3) . . . . ? C2 C1 C6 C5 -0.4(4) . . . . ? Br1 C1 C6 C5 176.7(2) . . . . ? C4 C5 C6 C1 -0.2(4) . . . . ? C7 C5 C6 C1 -179.3(3) . . . . ? C6 C5 C7 C8 179.2(3) . . . . ? C4 C5 C7 C8 0.0(3) . . . . ? C6 C5 C7 Br3 -2.0(5) . . . . ? C4 C5 C7 Br3 178.8(2) . . . . ? C5 C7 C8 N1 0.1(4) . . . . ? Br3 C7 C8 N1 -178.6(2) . . . . ? C3 C4 N1 C8 -179.7(3) . . . . ? C5 C4 N1 C8 0.2(4) . . . . ? C7 C8 N1 C4 -0.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Br2 0.88 2.72 3.583(3) 168.0 2_556 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.547 _refine_diff_density_min -0.744 _refine_diff_density_rms 0.120 #============================================================================== data_11 _database_code_depnum_ccdc_archive 'CCDC 818711' #TrackingRef 'Indoles.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5,6-Tribromo-N-methyl-1H-indole ; _chemical_name_common 3,5,6-Tribromo-N-methyl-1H-indole _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 Br3 N' _chemical_formula_sum 'C9 H6 Br3 N' _chemical_formula_weight 367.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6033(4) _cell_length_b 8.0327(4) _cell_length_c 9.6610(5) _cell_angle_alpha 68.061(3) _cell_angle_beta 66.835(3) _cell_angle_gamma 73.873(3) _cell_volume 497.24(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4901 _cell_measurement_theta_min 5.219 _cell_measurement_theta_max 70.245 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 14.635 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2030 _exptl_absorpt_correction_T_max 0.2520 _exptl_absorpt_process_details 'SADABS V2.07 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 4812 reflections reduced R(int) from 0.0419 to 0.0173 Ratio of minimum to maximum apparent transmission: 0.737228 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 6000' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4842 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 6.41 _diffrn_reflns_theta_max 66.59 _reflns_number_total 1695 _reflns_number_gt 1682 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART V5.626 (Bruker, 1997)' _computing_cell_refinement 'SAINT V6.28A (Bruker, 1997)' _computing_data_reduction 'SAINT V6.28A (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K, & Puschmann, H., 2009) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+0.9093P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1695 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0236 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0621 _refine_ls_wR_factor_gt 0.0619 _refine_ls_goodness_of_fit_ref 1.175 _refine_ls_restrained_S_all 1.175 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3021(4) 0.8939(4) 0.3942(4) 0.0129(6) Uani 1 1 d . . . C2 C 0.2277(4) 1.0811(4) 0.3551(4) 0.0133(6) Uani 1 1 d . . . C3 C 0.1819(4) 1.1780(4) 0.4593(4) 0.0129(6) Uani 1 1 d . . . H3 H 0.1330 1.3042 0.4320 0.015 Uiso 1 1 calc R . . C4 C 0.2089(4) 1.0874(4) 0.6053(4) 0.0115(6) Uani 1 1 d . . . C5 C 0.2846(4) 0.9001(4) 0.6423(4) 0.0116(6) Uani 1 1 d . . . C6 C 0.3322(4) 0.8021(4) 0.5361(4) 0.0137(6) Uani 1 1 d . . . H6 H 0.3835 0.6764 0.5616 0.016 Uiso 1 1 calc R . . C7 C 0.1785(5) 1.1370(4) 0.7405(4) 0.0139(6) Uani 1 1 d . . . C8 C 0.2318(4) 0.9873(4) 0.8517(4) 0.0134(6) Uani 1 1 d . . . H8 H 0.2253 0.9837 0.9529 0.016 Uiso 1 1 calc R . . C9 C 0.3612(5) 0.6537(4) 0.8774(4) 0.0163(7) Uani 1 1 d . . . H9A H 0.2878 0.5711 0.8770 0.024 Uiso 1 1 calc R . . H9B H 0.3388 0.6461 0.9865 0.024 Uiso 1 1 calc R . . H9C H 0.4995 0.6191 0.8258 0.024 Uiso 1 1 calc R . . N1 N 0.2969(4) 0.8420(4) 0.7910(3) 0.0130(5) Uani 1 1 d . . . Br1 Br 0.36179(5) 0.75950(5) 0.25276(4) 0.01928(12) Uani 1 1 d . . . Br2 Br 0.18931(5) 1.20471(4) 0.15642(4) 0.01626(12) Uani 1 1 d . . . Br3 Br 0.08521(5) 1.37032(4) 0.76432(4) 0.01782(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0128(15) 0.0161(15) 0.0120(15) -0.0093(13) -0.0006(12) -0.0036(12) C2 0.0139(15) 0.0169(16) 0.0083(14) -0.0020(12) -0.0031(12) -0.0044(12) C3 0.0141(15) 0.0105(14) 0.0141(16) -0.0031(12) -0.0048(13) -0.0021(12) C4 0.0103(15) 0.0112(15) 0.0131(15) -0.0057(12) -0.0023(12) -0.0012(11) C5 0.0108(14) 0.0137(15) 0.0125(15) -0.0059(12) -0.0037(12) -0.0028(11) C6 0.0131(15) 0.0126(15) 0.0170(16) -0.0058(13) -0.0061(13) -0.0007(12) C7 0.0150(15) 0.0135(16) 0.0140(15) -0.0075(13) -0.0040(13) 0.0002(12) C8 0.0155(16) 0.0140(15) 0.0124(15) -0.0070(13) -0.0034(13) -0.0023(12) C9 0.0217(17) 0.0071(15) 0.0259(18) -0.0065(13) -0.0167(15) 0.0045(12) N1 0.0175(13) 0.0099(13) 0.0126(13) -0.0033(11) -0.0070(11) -0.0003(10) Br1 0.0251(2) 0.0206(2) 0.0187(2) -0.01408(15) -0.00997(16) 0.00221(14) Br2 0.0229(2) 0.01717(19) 0.00973(18) -0.00346(14) -0.00697(14) -0.00288(14) Br3 0.0242(2) 0.01341(19) 0.0200(2) -0.00913(14) -0.01038(15) 0.00139(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.368(5) . ? C1 C2 1.413(5) . ? C1 Br1 1.892(3) . ? C2 C3 1.378(5) . ? C2 Br2 1.901(3) . ? C3 C4 1.393(5) . ? C3 H3 0.9500 . ? C4 C5 1.414(4) . ? C4 C7 1.421(4) . ? C5 N1 1.368(4) . ? C5 C6 1.399(4) . ? C6 H6 0.9500 . ? C7 C8 1.368(5) . ? C7 Br3 1.877(3) . ? C8 N1 1.383(4) . ? C8 H8 0.9500 . ? C9 N1 1.480(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.4(3) . . ? C6 C1 Br1 117.4(2) . . ? C2 C1 Br1 121.2(2) . . ? C3 C2 C1 121.1(3) . . ? C3 C2 Br2 118.6(2) . . ? C1 C2 Br2 120.4(2) . . ? C2 C3 C4 118.6(3) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C3 C4 C5 119.6(3) . . ? C3 C4 C7 135.3(3) . . ? C5 C4 C7 105.1(3) . . ? N1 C5 C6 129.5(3) . . ? N1 C5 C4 108.8(3) . . ? C6 C5 C4 121.7(3) . . ? C1 C6 C5 117.6(3) . . ? C1 C6 H6 121.2 . . ? C5 C6 H6 121.2 . . ? C8 C7 C4 109.1(3) . . ? C8 C7 Br3 124.7(2) . . ? C4 C7 Br3 126.2(2) . . ? C7 C8 N1 108.1(3) . . ? C7 C8 H8 125.9 . . ? N1 C8 H8 125.9 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 N1 C8 108.9(3) . . ? C5 N1 C9 126.3(3) . . ? C8 N1 C9 124.8(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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.2(5) . . . . ? Br1 C1 C2 C3 179.1(2) . . . . ? C6 C1 C2 Br2 179.6(2) . . . . ? Br1 C1 C2 Br2 -1.1(4) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? Br2 C2 C3 C4 179.6(2) . . . . ? C2 C3 C4 C5 0.9(4) . . . . ? C2 C3 C4 C7 -179.3(3) . . . . ? C3 C4 C5 N1 -179.8(3) . . . . ? C7 C4 C5 N1 0.4(3) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C7 C4 C5 C6 179.6(3) . . . . ? C2 C1 C6 C5 0.6(4) . . . . ? Br1 C1 C6 C5 -178.7(2) . . . . ? N1 C5 C6 C1 178.8(3) . . . . ? C4 C5 C6 C1 -0.2(4) . . . . ? C3 C4 C7 C8 179.8(3) . . . . ? C5 C4 C7 C8 -0.4(4) . . . . ? C3 C4 C7 Br3 -1.4(5) . . . . ? C5 C4 C7 Br3 178.4(2) . . . . ? C4 C7 C8 N1 0.3(4) . . . . ? Br3 C7 C8 N1 -178.6(2) . . . . ? C6 C5 N1 C8 -179.4(3) . . . . ? C4 C5 N1 C8 -0.3(3) . . . . ? C6 C5 N1 C9 -1.8(5) . . . . ? C4 C5 N1 C9 177.4(3) . . . . ? C7 C8 N1 C5 0.0(4) . . . . ? C7 C8 N1 C9 -177.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.605 _refine_diff_density_min -0.802 _refine_diff_density_rms 0.167