# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'J.E. Davies' _publ_contact_author_email jed2@cam.ac.uk loop_ _publ_author_name C.Smith C.Smith N.Nikbin S.Ley I.R.Baxendale data_sl0851 _database_code_depnum_ccdc_archive 'CCDC 791578' #TrackingRef 'sl0851.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N O2' _chemical_formula_sum 'C13 H13 N O2' _chemical_formula_weight 215.24 _chemical_absolute_configuration ; 2125 Friedel pairs were averaged for the refinement ; 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca2(1) _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 8.8940(3) _cell_length_b 8.4670(3) _cell_length_c 15.2509(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1148.48(7) _cell_formula_units_Z 4 _cell_measurement_temperature 260(2) _cell_measurement_reflns_used 4471 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.939 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 260(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5219 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1348 _reflns_number_gt 1221 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^ > 2sigma(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^)+(0.0479P)^2^+0.1002P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(16) _refine_ls_number_reflns 1348 _refine_ls_number_parameters 147 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 N1 N 0.9845(2) 0.2850(2) 0.73088(12) 0.0499(4) Uani 1 1 d . . . O1 O 1.50928(18) 0.2074(2) 0.53536(12) 0.0616(4) Uani 1 1 d . . . O2 O 0.71398(15) 0.31330(15) 0.82716(10) 0.0510(4) Uani 1 1 d . . . C1 C 1.1156(2) 0.2635(2) 0.67918(14) 0.0453(4) Uani 1 1 d . . . C2 C 1.2405(3) 0.3547(2) 0.69905(17) 0.0558(5) Uani 1 1 d . . . H2 H 1.2341 0.4285 0.7440 0.067 Uiso 1 1 calc R . . C3 C 1.3743(2) 0.3389(2) 0.65387(16) 0.0541(5) Uani 1 1 d . . . H3 H 1.4575 0.3991 0.6695 0.065 Uiso 1 1 calc R . . C4 C 1.3833(2) 0.2327(2) 0.58521(14) 0.0474(5) Uani 1 1 d . . . C5 C 1.2579(3) 0.1436(3) 0.56319(14) 0.0549(5) Uani 1 1 d . . . H5 H 1.2635 0.0731 0.5166 0.066 Uiso 1 1 calc R . . C6 C 1.1249(2) 0.1578(3) 0.60922(14) 0.0521(5) Uani 1 1 d . . . H6 H 1.0419 0.0972 0.5937 0.062 Uiso 1 1 calc R . . C7 C 1.6448(2) 0.2828(3) 0.5627(2) 0.0682(7) Uani 1 1 d . . . H7A H 1.7245 0.2559 0.5229 0.102 Uiso 1 1 calc R . . H7B H 1.6705 0.2479 0.6207 0.102 Uiso 1 1 calc R . . H7C H 1.6307 0.3952 0.5629 0.102 Uiso 1 1 calc R . . C8 C 0.9041(2) 0.1639(2) 0.74874(14) 0.0448(4) Uani 1 1 d . . . H8 H 0.9343 0.0665 0.7268 0.054 Uiso 1 1 calc R . . C9 C 0.7700(2) 0.1701(2) 0.80063(13) 0.0441(4) Uani 1 1 d . . . C10 C 0.6823(2) 0.0529(2) 0.83322(14) 0.0495(4) Uani 1 1 d . . . H10 H 0.6960 -0.0550 0.8252 0.059 Uiso 1 1 calc R . . C11 C 0.5658(2) 0.1261(3) 0.88185(15) 0.0519(5) Uani 1 1 d . . . H11 H 0.4885 0.0754 0.9118 0.062 Uiso 1 1 calc R . . C12 C 0.5885(2) 0.2831(2) 0.87643(16) 0.0512(5) Uani 1 1 d . . . C13 C 0.5088(3) 0.4227(3) 0.9114(2) 0.0737(7) Uani 1 1 d . . . H13A H 0.4187 0.3894 0.9407 0.111 Uiso 1 1 calc R . . H13B H 0.4834 0.4925 0.8641 0.111 Uiso 1 1 calc R . . H13C H 0.5727 0.4769 0.9523 0.111 Uiso 1 1 calc R . . 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 N1 0.0503(9) 0.0456(9) 0.0537(10) -0.0003(8) 0.0061(8) 0.0038(7) O1 0.0532(8) 0.0719(10) 0.0596(9) -0.0018(8) 0.0109(7) 0.0059(8) O2 0.0495(7) 0.0475(7) 0.0561(9) 0.0055(6) 0.0083(7) 0.0052(6) C1 0.0473(10) 0.0397(9) 0.0490(11) 0.0037(8) 0.0030(9) 0.0061(7) C2 0.0597(11) 0.0445(9) 0.0633(13) -0.0123(9) 0.0120(10) -0.0010(10) C3 0.0522(11) 0.0468(10) 0.0634(13) -0.0037(9) 0.0061(10) -0.0043(9) C4 0.0480(11) 0.0478(10) 0.0464(11) 0.0043(8) 0.0045(8) 0.0081(8) C5 0.0576(11) 0.0617(11) 0.0454(11) -0.0102(9) 0.0008(9) 0.0019(11) C6 0.0504(11) 0.0577(11) 0.0481(11) -0.0044(9) -0.0038(9) -0.0012(9) C7 0.0481(11) 0.0842(16) 0.0723(15) 0.0078(13) 0.0102(11) 0.0082(12) C8 0.0436(9) 0.0459(9) 0.0450(9) 0.0008(8) -0.0040(8) 0.0055(8) C9 0.0422(9) 0.0452(9) 0.0450(10) 0.0018(8) -0.0057(8) 0.0037(8) C10 0.0474(9) 0.0486(10) 0.0525(10) -0.0024(9) -0.0066(9) -0.0057(8) C11 0.0449(9) 0.0616(12) 0.0492(10) 0.0013(10) -0.0028(9) -0.0102(9) C12 0.0444(9) 0.0623(12) 0.0471(10) 0.0027(11) 0.0004(9) 0.0048(8) C13 0.0699(15) 0.0692(16) 0.0820(17) 0.0012(13) 0.0221(13) 0.0158(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 N1 C8 1.280(3) . ? N1 C1 1.419(3) . ? O1 C4 1.371(2) . ? O1 C7 1.426(3) . ? O2 C12 1.370(3) . ? O2 C9 1.372(2) . ? C1 C2 1.386(3) . ? C1 C6 1.395(3) . ? C2 C3 1.381(3) . ? C2 H2 0.9300 . ? C3 C4 1.382(3) . ? C3 H3 0.9300 . ? C4 C5 1.387(3) . ? C5 C6 1.381(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.432(3) . ? C8 H8 0.9300 . ? C9 C10 1.356(3) . ? C10 C11 1.417(3) . ? C10 H10 0.9300 . ? C11 C12 1.347(3) . ? C11 H11 0.9300 . ? C12 C13 1.478(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 C8 N1 C1 118.34(17) . . ? C4 O1 C7 117.32(19) . . ? C12 O2 C9 107.00(15) . . ? C2 C1 C6 118.5(2) . . ? C2 C1 N1 117.75(19) . . ? C6 C1 N1 123.79(19) . . ? C3 C2 C1 121.8(2) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 C3 C4 119.4(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? O1 C4 C3 124.7(2) . . ? O1 C4 C5 115.98(19) . . ? C3 C4 C5 119.4(2) . . ? C6 C5 C4 121.21(19) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 119.7(2) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 123.63(18) . . ? N1 C8 H8 118.2 . . ? C9 C8 H8 118.2 . . ? C10 C9 O2 109.25(17) . . ? C10 C9 C8 130.89(18) . . ? O2 C9 C8 119.84(16) . . ? C9 C10 C11 107.01(19) . . ? C9 C10 H10 126.5 . . ? C11 C10 H10 126.5 . . ? C12 C11 C10 106.86(19) . . ? C12 C11 H11 126.6 . . ? C10 C11 H11 126.6 . . ? C11 C12 O2 109.87(18) . . ? C11 C12 C13 134.1(2) . . ? O2 C12 C13 116.04(19) . . ? 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 . . ? 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 C8 N1 C1 C2 -143.6(2) . . . . ? C8 N1 C1 C6 37.3(3) . . . . ? C6 C1 C2 C3 -2.6(3) . . . . ? N1 C1 C2 C3 178.2(2) . . . . ? C1 C2 C3 C4 1.9(3) . . . . ? C7 O1 C4 C3 7.5(3) . . . . ? C7 O1 C4 C5 -172.7(2) . . . . ? C2 C3 C4 O1 179.6(2) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? O1 C4 C5 C6 179.42(19) . . . . ? C3 C4 C5 C6 -0.7(3) . . . . ? C4 C5 C6 C1 0.1(3) . . . . ? C2 C1 C6 C5 1.6(3) . . . . ? N1 C1 C6 C5 -179.27(19) . . . . ? C1 N1 C8 C9 179.63(18) . . . . ? C12 O2 C9 C10 -0.5(2) . . . . ? C12 O2 C9 C8 -178.92(19) . . . . ? N1 C8 C9 C10 -171.8(2) . . . . ? N1 C8 C9 O2 6.1(3) . . . . ? O2 C9 C10 C11 0.4(2) . . . . ? C8 C9 C10 C11 178.5(2) . . . . ? C9 C10 C11 C12 0.0(2) . . . . ? C10 C11 C12 O2 -0.3(2) . . . . ? C10 C11 C12 C13 179.8(3) . . . . ? C9 O2 C12 C11 0.5(2) . . . . ? C9 O2 C12 C13 -179.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.108 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.025 # Attachment 'sl1002.cif' data_sl1002 _database_code_depnum_ccdc_archive 'CCDC 791581' #TrackingRef 'sl1002.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 Br N4' _chemical_formula_sum 'C7 H3 Br N4' _chemical_formula_weight 223.04 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' 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4355(1) _cell_length_b 8.5948(2) _cell_length_c 13.7214(3) _cell_angle_alpha 88.715(1) _cell_angle_beta 89.784(1) _cell_angle_gamma 68.818(1) _cell_volume 817.43(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9841 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 31.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.812 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 4.972 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.421 _exptl_absorpt_correction_T_max 0.782 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 15517 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 30.98 _reflns_number_total 5189 _reflns_number_gt 4192 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^ > 2sigma(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^)+(0.0573P)^2^+0.3243P] 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 5189 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1102 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 Br1 Br 0.00148(4) 0.30018(4) 0.13809(2) 0.04792(9) Uani 1 1 d . . . N1 N 0.4545(3) -0.2385(2) -0.14195(15) 0.0346(4) Uani 1 1 d . . . N2 N 0.5653(3) -0.3750(2) -0.10780(16) 0.0353(4) Uani 1 1 d . . . N3 N 0.6701(3) -0.5029(3) -0.0876(2) 0.0499(6) Uani 1 1 d . . . N4 N 0.1506(4) 0.0698(3) -0.29376(17) 0.0488(6) Uani 1 1 d . . . C1 C 0.3553(3) -0.1203(3) -0.07183(16) 0.0294(4) Uani 1 1 d . . . C2 C 0.2190(3) 0.0292(3) -0.10890(16) 0.0295(4) Uani 1 1 d . . . C3 C 0.1151(3) 0.1554(3) -0.04604(17) 0.0330(4) Uani 1 1 d . . . H3A H 0.0240 0.2571 -0.0712 0.040 Uiso 1 1 calc R . . C4 C 0.1465(3) 0.1304(3) 0.05321(18) 0.0348(5) Uani 1 1 d . . . C5 C 0.2798(4) -0.0176(3) 0.09103(17) 0.0364(5) Uani 1 1 d . . . H5A H 0.2990 -0.0334 0.1595 0.044 Uiso 1 1 calc R . . C6 C 0.3850(3) -0.1422(3) 0.02828(17) 0.0321(4) Uani 1 1 d . . . H6A H 0.4775 -0.2427 0.0539 0.039 Uiso 1 1 calc R . . C7 C 0.1831(3) 0.0514(3) -0.21223(17) 0.0343(5) Uani 1 1 d . . . Br1' Br 0.16830(4) -0.44280(3) 0.34636(2) 0.04518(9) Uani 1 1 d . . . N1' N 0.6831(3) -0.9341(2) 0.64585(15) 0.0380(4) Uani 1 1 d . . . N2' N 0.8229(3) -1.0547(3) 0.61583(16) 0.0382(4) Uani 1 1 d . . . N3' N 0.9508(4) -1.1679(3) 0.5989(2) 0.0524(6) Uani 1 1 d . . . N4' N 0.3563(4) -0.6264(3) 0.78658(17) 0.0480(5) Uani 1 1 d . . . C1' C 0.5699(3) -0.8249(3) 0.57147(17) 0.0308(4) Uani 1 1 d . . . C2' C 0.4164(3) -0.6844(3) 0.60323(16) 0.0308(4) Uani 1 1 d . . . C3' C 0.2968(3) -0.5710(3) 0.53539(17) 0.0325(4) Uani 1 1 d . . . H3'A H 0.1928 -0.4760 0.5566 0.039 Uiso 1 1 calc R . . C4' C 0.3309(3) -0.5981(3) 0.43691(17) 0.0330(4) Uani 1 1 d . . . C5' C 0.4825(4) -0.7364(3) 0.40469(17) 0.0367(5) Uani 1 1 d . . . H5'A H 0.5048 -0.7533 0.3368 0.044 Uiso 1 1 calc R . . C6' C 0.6016(3) -0.8501(3) 0.47210(17) 0.0348(5) Uani 1 1 d . . . H6'A H 0.7049 -0.9451 0.4502 0.042 Uiso 1 1 calc R . . C7' C 0.3849(3) -0.6542(3) 0.70589(17) 0.0356(5) 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 Br1 0.04915(16) 0.05066(16) 0.05044(17) -0.02516(12) 0.01916(12) -0.02464(13) N1 0.0339(9) 0.0283(8) 0.0364(10) -0.0016(7) 0.0005(8) -0.0051(7) N2 0.0322(9) 0.0311(9) 0.0422(11) -0.0016(8) 0.0034(8) -0.0110(8) N3 0.0429(12) 0.0320(10) 0.0672(16) 0.0041(10) 0.0044(11) -0.0048(9) N4 0.0567(14) 0.0367(11) 0.0394(11) -0.0033(9) -0.0049(10) -0.0002(10) C1 0.0277(9) 0.0275(9) 0.0341(10) -0.0018(8) 0.0015(8) -0.0111(8) C2 0.0278(9) 0.0287(9) 0.0310(10) -0.0027(8) 0.0014(8) -0.0089(8) C3 0.0292(10) 0.0317(10) 0.0380(11) -0.0061(8) 0.0034(8) -0.0105(8) C4 0.0331(10) 0.0373(11) 0.0381(11) -0.0123(9) 0.0088(9) -0.0174(9) C5 0.0401(12) 0.0463(12) 0.0299(11) -0.0036(9) 0.0026(9) -0.0242(10) C6 0.0325(10) 0.0317(10) 0.0340(11) 0.0010(8) -0.0009(8) -0.0139(8) C7 0.0335(10) 0.0285(9) 0.0348(11) -0.0050(8) -0.0003(9) -0.0036(8) Br1' 0.04421(15) 0.04877(15) 0.04266(15) 0.00980(11) -0.00776(11) -0.01747(12) N1' 0.0384(10) 0.0320(9) 0.0369(10) -0.0060(8) 0.0019(8) -0.0043(8) N2' 0.0368(10) 0.0321(9) 0.0423(11) -0.0072(8) 0.0026(8) -0.0081(8) N3' 0.0439(12) 0.0387(11) 0.0646(16) -0.0106(11) 0.0014(11) -0.0025(10) N4' 0.0496(12) 0.0447(12) 0.0374(11) -0.0069(9) 0.0034(9) -0.0017(10) C1' 0.0314(10) 0.0282(9) 0.0325(10) -0.0060(8) 0.0035(8) -0.0102(8) C2' 0.0319(10) 0.0297(9) 0.0307(10) -0.0071(8) 0.0031(8) -0.0105(8) C3' 0.0317(10) 0.0292(9) 0.0359(11) -0.0059(8) 0.0022(8) -0.0101(8) C4' 0.0345(10) 0.0342(10) 0.0329(10) -0.0020(8) 0.0007(8) -0.0154(9) C5' 0.0417(12) 0.0406(11) 0.0294(10) -0.0053(9) 0.0044(9) -0.0165(10) C6' 0.0363(11) 0.0336(10) 0.0341(11) -0.0102(8) 0.0070(9) -0.0116(9) C7' 0.0347(11) 0.0314(10) 0.0343(11) -0.0059(9) 0.0037(9) -0.0038(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 Br1 C4 1.892(2) . ? N1 N2 1.247(3) . ? N1 C1 1.414(3) . ? N2 N3 1.123(3) . ? N4 C7 1.141(3) . ? C1 C6 1.390(3) . ? C1 C2 1.404(3) . ? C2 C3 1.396(3) . ? C2 C7 1.439(3) . ? C3 C4 1.382(3) . ? C3 H3A 0.9500 . ? C4 C5 1.390(3) . ? C5 C6 1.389(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? Br1' C4' 1.886(2) . ? N1' N2' 1.250(3) . ? N1' C1' 1.423(3) . ? N2' N3' 1.116(3) . ? N4' C7' 1.141(3) . ? C1' C6' 1.391(3) . ? C1' C2' 1.405(3) . ? C2' C3' 1.395(3) . ? C2' C7' 1.441(3) . ? C3' C4' 1.383(3) . ? C3' H3'A 0.9500 . ? C4' C5' 1.389(3) . ? C5' C6' 1.391(3) . ? C5' H5'A 0.9500 . ? C6' H6'A 0.9500 . ? 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 N2 N1 C1 115.0(2) . . ? N3 N2 N1 172.2(3) . . ? C6 C1 C2 119.4(2) . . ? C6 C1 N1 124.88(19) . . ? C2 C1 N1 115.8(2) . . ? C3 C2 C1 120.4(2) . . ? C3 C2 C7 119.7(2) . . ? C1 C2 C7 119.8(2) . . ? C4 C3 C2 119.1(2) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 121.1(2) . . ? C3 C4 Br1 118.87(18) . . ? C5 C4 Br1 120.03(18) . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? C5 C6 C1 120.3(2) . . ? C5 C6 H6A 119.9 . . ? C1 C6 H6A 119.9 . . ? N4 C7 C2 178.5(3) . . ? N2' N1' C1' 114.9(2) . . ? N3' N2' N1' 172.8(3) . . ? C6' C1' C2' 119.6(2) . . ? C6' C1' N1' 124.3(2) . . ? C2' C1' N1' 116.1(2) . . ? C3' C2' C1' 120.1(2) . . ? C3' C2' C7' 119.6(2) . . ? C1' C2' C7' 120.2(2) . . ? C4' C3' C2' 119.4(2) . . ? C4' C3' H3'A 120.3 . . ? C2' C3' H3'A 120.3 . . ? C3' C4' C5' 121.0(2) . . ? C3' C4' Br1' 118.77(17) . . ? C5' C4' Br1' 120.26(18) . . ? C4' C5' C6' 119.8(2) . . ? C4' C5' H5'A 120.1 . . ? C6' C5' H5'A 120.1 . . ? C5' C6' C1' 120.1(2) . . ? C5' C6' H6'A 119.9 . . ? C1' C6' H6'A 119.9 . . ? N4' C7' C2' 178.2(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 C1 N1 N2 N3 -178.5(18) . . . . ? N2 N1 C1 C6 5.3(3) . . . . ? N2 N1 C1 C2 -175.3(2) . . . . ? C6 C1 C2 C3 0.5(3) . . . . ? N1 C1 C2 C3 -179.0(2) . . . . ? C6 C1 C2 C7 -178.3(2) . . . . ? N1 C1 C2 C7 2.3(3) . . . . ? C1 C2 C3 C4 -0.8(3) . . . . ? C7 C2 C3 C4 177.9(2) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C2 C3 C4 Br1 -178.78(17) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? Br1 C4 C5 C6 179.60(17) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? C2 C1 C6 C5 0.4(3) . . . . ? N1 C1 C6 C5 179.8(2) . . . . ? C3 C2 C7 N4 -52(10) . . . . ? C1 C2 C7 N4 127(10) . . . . ? C1' N1' N2' N3' -175(2) . . . . ? N2' N1' C1' C6' 3.0(4) . . . . ? N2' N1' C1' C2' -177.5(2) . . . . ? C6' C1' C2' C3' 0.0(3) . . . . ? N1' C1' C2' C3' -179.5(2) . . . . ? C6' C1' C2' C7' -178.3(2) . . . . ? N1' C1' C2' C7' 2.1(3) . . . . ? C1' C2' C3' C4' -0.1(3) . . . . ? C7' C2' C3' C4' 178.2(2) . . . . ? C2' C3' C4' C5' 0.0(3) . . . . ? C2' C3' C4' Br1' -179.68(17) . . . . ? C3' C4' C5' C6' 0.3(4) . . . . ? Br1' C4' C5' C6' 179.95(18) . . . . ? C4' C5' C6' C1' -0.4(4) . . . . ? C2' C1' C6' C5' 0.2(4) . . . . ? N1' C1' C6' C5' 179.8(2) . . . . ? C3' C2' C7' N4' -6(10) . . . . ? C1' C2' C7' N4' 172(10) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.98 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.511 _refine_diff_density_min -1.288 _refine_diff_density_rms 0.104