# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/195 data_1a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H14 Br N3' _chemical_formula_weight 184.09 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 Tetragonal _symmetry_space_group_name_H-M P-421m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'y, -x, -z' '-x, -y, z' '-y, x, -z' '-x+1/2, y+1/2, -z' '-y+1/2, -x+1/2, z' 'x+1/2, -y+1/2, -z' 'y+1/2, x+1/2, z' _cell_length_a 8.6698(4) _cell_length_b 8.6698(4) _cell_length_c 5.2977(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 398.20(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow ' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_absorpt_coefficient_mu 5.080 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2896 _diffrn_reflns_av_R_equivalents 0.088 _diffrn_reflns_av_sigmaI/netI 0.0415 _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 -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 25.96 _reflns_number_total 426 _reflns_number_gt 382 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0270P)^2^+0.0520P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.100(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.51(6) _refine_ls_number_reflns 426 _refine_ls_number_parameters 30 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0641 _refine_ls_goodness_of_fit_ref 1.193 _refine_ls_restrained_S_all 1.193 _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 Br1 Br -0.5000 0.5000 1.0000 0.0142(3) Uani 1 4 d S . . N1 N 0.3021(2) 0.8021(2) 0.7110(6) 0.0119(7) Uani 1 2 d S . . H11 H 0.3587 0.7451 0.8073 0.013(7) Uiso 1 1 d R . . N2 N 0.0000 0.5000 0.5530(7) 0.0099(8) Uani 1 4 d S . . H21 H 0.0763 0.4237 0.4775 0.08(2) Uiso 1 2 d SR . . C1 C 0.2042(3) 0.7042(3) 0.5501(6) 0.0129(8) Uani 1 2 d S . . H1B H 0.2701 0.6394 0.4404 0.015 Uiso 0.50 1 calc PR . . H1A H 0.1394 0.7701 0.4404 0.015 Uiso 0.50 1 calc PR . . C2 C 0.1009(2) 0.6009(2) 0.7120(7) 0.0109(7) Uani 1 2 d S . . H2B H 0.1662 0.5356 0.8219 0.013 Uiso 0.50 1 calc PR . . H2A H 0.0356 0.6662 0.8219 0.013 Uiso 0.50 1 calc PR . . 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 0.0086(3) 0.0086(3) 0.0256(4) 0.000 0.000 0.000 N1 0.0063(9) 0.0063(9) 0.0231(15) -0.0007(9) -0.0007(9) -0.0031(15) N2 0.0052(12) 0.0052(12) 0.0192(18) 0.000 0.000 -0.003(2) C1 0.0094(11) 0.0094(11) 0.020(2) 0.0011(11) 0.0011(11) -0.0079(19) C2 0.0069(10) 0.0069(10) 0.0189(16) 0.0004(10) 0.0004(10) -0.0054(17) _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 C1 1.472(5) . ? N2 C2 1.497(3) . ? N2 C2 1.497(3) 3_565 ? C1 C2 1.529(5) . ? 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 C2 N2 C2 111.5(3) . 3_565 ? N1 C1 C2 110.5(3) . . ? N2 C2 C1 111.7(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 C2 N2 C2 C1 180.0 3_565 . . . ? N1 C1 C2 N2 180.0 . . . . ? 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 H11 Br1 0.86 2.66 3.4853(14) 161.3 1_655 N2 H21 N1 1.02 1.79 2.800(4) 169.3 4_656 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.281 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.118 #===END data_1b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H15 Cl2 N3' _chemical_formula_weight 176.09 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Orthorhombic P ' _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 8.6597(6) _cell_length_b 8.7948(4) _cell_length_c 11.9359(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 909.04(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.647 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6490 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 26.00 _reflns_number_total 950 _reflns_number_gt 880 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0242P)^2^+0.3019P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.010(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 950 _refine_ls_number_parameters 51 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0585 _refine_ls_wR_factor_gt 0.0574 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 Cl1 Cl 0.61471(5) 0.2500 0.31321(3) 0.01668(15) Uani 1 2 d S . . N1 N 0.32800(12) 0.01383(11) 0.32989(8) 0.0154(2) Uani 1 1 d . . . H13 H 0.3955 0.0932 0.3332 0.026(4) Uiso 1 1 d R . . H12 H 0.2523 0.0379 0.2856 0.023(4) Uiso 1 1 d R . . H11 H 0.3796 -0.0648 0.3018 0.024(4) Uiso 1 1 d R . . N2 N 0.26232(17) 0.2500 0.48462(12) 0.0149(3) Uani 1 2 d S . . H21 H 0.3232 0.2500 0.5421 0.018(5) Uiso 1 2 d SR . . C1 C 0.26494(15) -0.02266(14) 0.44353(10) 0.0180(3) Uani 1 1 d . . . H1B H 0.3510 -0.0436 0.4959 0.022 Uiso 1 1 calc R . . H1A H 0.1994 -0.1147 0.4392 0.022 Uiso 1 1 calc R . . C2 C 0.17000(15) 0.11060(14) 0.48649(10) 0.0178(3) Uani 1 1 d . . . H2B H 0.0773 0.1238 0.4390 0.021 Uiso 1 1 calc R . . H2A H 0.1353 0.0897 0.5640 0.021 Uiso 1 1 calc R . . Cl2 Cl 0.44047(5) 0.2500 0.73921(3) 0.01630(15) Uani 1 2 d S . . 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 Cl1 0.0178(3) 0.0153(2) 0.0169(2) 0.000 0.00436(15) 0.000 N1 0.0157(5) 0.0141(5) 0.0163(5) -0.0004(4) -0.0007(4) 0.0013(4) N2 0.0150(7) 0.0139(7) 0.0159(7) 0.000 -0.0017(6) 0.000 C1 0.0225(7) 0.0148(6) 0.0165(6) 0.0030(5) 0.0000(5) -0.0026(5) C2 0.0196(6) 0.0185(7) 0.0154(6) 0.0002(5) 0.0037(5) -0.0041(5) Cl2 0.0153(2) 0.0163(2) 0.0173(2) 0.000 0.00150(15) 0.000 _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 C1 1.4970(15) . ? N2 C2 1.4638(14) . ? N2 C2 1.4638(14) 7_565 ? C1 C2 1.5207(17) . ? 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 C2 N2 C2 113.77(14) . 7_565 ? N1 C1 C2 109.73(9) . . ? N2 C2 C1 110.19(10) . . ? 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 C2 N2 C2 C1 159.94(8) 7_565 . . . ? N1 C1 C2 N2 -54.82(13) . . . . ? 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 H13 Cl1 0.91 2.36 3.2432(11) 163.7 . N1 H12 Cl1 0.87 2.51 3.2624(10) 145.7 6_556 N1 H11 Cl2 0.89 2.31 3.1756(11) 165.6 5_656 N2 H21 Cl2 0.87 2.56 3.4080(15) 165.8 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.268 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.058 #===END data_1c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H15 Br2 N3' _chemical_formula_weight 265.01 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 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 11.6664(10) _cell_length_b 9.1552(5) _cell_length_c 17.5536(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1874.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.878 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 8.583 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9938 _diffrn_reflns_av_R_equivalents 0.068 _diffrn_reflns_av_sigmaI/netI 0.0791 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1812 _reflns_number_gt 1503 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0000P)^2^+5.0548P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0011(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 1812 _refine_ls_number_parameters 90 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.03564(5) 0.05263(4) 0.37045(2) 0.01272(18) Uani 1 1 d . . . Br2 Br 0.00992(5) -0.51074(4) 0.38011(2) 0.01618(18) Uani 1 1 d . . . N1 N -0.2522(4) -0.4007(3) 0.2481(2) 0.0149(8) Uani 1 1 d . . . H13 H -0.2760 -0.4181 0.3005 0.05(2) Uiso 1 1 d R . . H12 H -0.1545 -0.4299 0.2423 0.026(15) Uiso 1 1 d R . . H11 H -0.3188 -0.4415 0.2024 0.08(2) Uiso 1 1 d R . . N2 N -0.2467(4) -0.2405(3) 0.3750(2) 0.0130(9) Uani 1 1 d . . . H21 H -0.3286 -0.1926 0.3781 0.06(2) Uiso 1 1 d R . . N3 N -0.2746(4) -0.3952(3) 0.5028(2) 0.0145(8) Uani 1 1 d . . . H33 H -0.3217 -0.4230 0.4483 0.05(2) Uiso 1 1 d R . . H32 H -0.1743 -0.4247 0.5116 0.05(2) Uiso 1 1 d R . . H31 H -0.3334 -0.4250 0.5378 0.011(13) Uiso 1 1 d R . . C1 C -0.2355(5) -0.2730(4) 0.2368(3) 0.0142(11) Uani 1 1 d . . . H1B H -0.3328 -0.2370 0.2309 0.017 Uiso 1 1 calc R . . H1A H -0.1782 -0.2577 0.1900 0.017 Uiso 1 1 calc R . . C2 C -0.1578(5) -0.2226(4) 0.3056(2) 0.0142(10) Uani 1 1 d . . . H2B H -0.0614 -0.2598 0.3118 0.017 Uiso 1 1 calc R . . H2A H -0.1417 -0.1395 0.2976 0.017 Uiso 1 1 calc R . . C3 C -0.1610(5) -0.2236(4) 0.4457(3) 0.0156(10) Uani 1 1 d . . . H3B H -0.1409 -0.1410 0.4531 0.019 Uiso 1 1 calc R . . H3A H -0.0664 -0.2642 0.4417 0.019 Uiso 1 1 calc R . . C4 C -0.2468(5) -0.2697(4) 0.5132(3) 0.0132(11) Uani 1 1 d . . . H4B H -0.1909 -0.2570 0.5608 0.016 Uiso 1 1 calc R . . H4A H -0.3409 -0.2284 0.5176 0.016 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 Br1 0.0152(3) 0.0133(3) 0.0096(3) -0.00051(18) -0.00022(15) 0.00060(16) Br2 0.0175(3) 0.0196(3) 0.0114(3) 0.00002(19) 0.00047(15) 0.00426(18) N1 0.019(2) 0.014(2) 0.012(2) 0.0002(18) -0.0009(15) -0.0002(14) N2 0.014(2) 0.016(2) 0.009(2) -0.0003(17) 0.0010(14) 0.0016(14) N3 0.017(2) 0.014(2) 0.013(2) 0.0027(18) 0.0015(15) -0.0022(16) C1 0.021(3) 0.012(3) 0.010(2) 0.0003(19) -0.0006(17) 0.0018(17) C2 0.018(2) 0.012(3) 0.013(2) 0.0027(19) 0.0044(18) -0.0035(17) C3 0.018(2) 0.014(3) 0.014(2) 0.000(2) -0.0001(18) -0.0019(18) C4 0.018(2) 0.012(3) 0.010(2) -0.0026(19) -0.0019(17) -0.0030(17) _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 C1 1.511(6) . ? N2 C2 1.481(5) . ? N2 C3 1.482(5) . ? N3 C4 1.497(6) . ? C1 C2 1.520(6) . ? C3 C4 1.520(6) . ? 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 C2 N2 C3 112.4(3) . . ? N1 C1 C2 108.9(4) . . ? N2 C2 C1 110.0(4) . . ? N2 C3 C4 109.4(4) . . ? N3 C4 C3 109.8(4) . . ? 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 C3 N2 C2 C1 163.9(4) . . . . ? N1 C1 C2 N2 -62.2(5) . . . . ? C2 N2 C3 C4 -166.9(4) . . . . ? N2 C3 C4 N3 60.6(5) . . . . ? 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 H13 Br1 0.97 2.64 3.395(4) 135.7 3_445 N1 H12 Br1 0.96 2.64 3.402(4) 136.0 8_556 N1 H12 Br2 0.96 3.00 3.575(4) 119.4 . N1 H11 Br2 1.11 2.21 3.298(4) 165.7 6_546 N2 H21 Br2 0.94 2.80 3.683(4) 158.5 3_445 N3 H33 Br1 1.10 2.42 3.434(4) 152.6 3_445 N3 H32 Br2 0.99 2.54 3.361(4) 140.1 5_546 N3 H32 Br2 0.99 3.03 3.639(4) 120.8 . N3 H31 Br1 0.89 2.47 3.321(4) 161.4 7_556 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.281 _refine_diff_density_min -1.297 _refine_diff_density_rms 0.162 #===END data_1d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H15 I2 N3' _chemical_formula_weight 358.99 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' 'I' 'I' -0.4742 1.8119 '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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.035(2) _cell_length_b 9.7006(19) _cell_length_c 18.374(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2145.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 5.808 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16401 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0783 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2092 _reflns_number_gt 1846 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0000P)^2^+4.2286P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00214(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 2092 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.257 _refine_ls_shift/su_mean 0.002 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 I1 I 0.55933(3) 0.03313(4) 0.371031(16) 0.01652(17) Uani 1 1 d . . . I2 I -0.01434(3) 0.00994(4) 0.379493(16) 0.01998(17) Uani 1 1 d . . . N2 N 0.2560(4) -0.2533(6) 0.37475(19) 0.0203(11) Uani 1 1 d . . . H21 H 0.293(5) -0.340(9) 0.370(3) 0.036(19) Uiso 1 1 d . . . N1 N 0.1093(4) -0.2718(6) 0.4987(3) 0.0195(10) Uani 1 1 d . . . H13 H 0.090(5) -0.343(7) 0.538(4) 0.05(2) Uiso 1 1 d . . . H12 H 0.091(5) -0.309(7) 0.462(4) 0.030(19) Uiso 1 1 d . . . H11 H 0.078(6) -0.177(8) 0.512(4) 0.04(2) Uiso 1 1 d . . . N3 N 0.1049(4) -0.2490(6) 0.2530(3) 0.0187(10) Uani 1 1 d . . . H33 H 0.069(5) -0.288(6) 0.299(3) 0.023(15) Uiso 1 1 d . . . H32 H 0.067(5) -0.173(8) 0.246(4) 0.04(2) Uiso 1 1 d . . . H31 H 0.076(5) -0.292(7) 0.226(3) 0.016(18) Uiso 1 1 d . . . C2 C 0.2796(5) -0.1779(7) 0.4421(3) 0.0226(13) Uani 1 1 d . . . H2B H 0.359(7) -0.143(8) 0.445(4) 0.07(2) Uiso 1 1 d . . . H2A H 0.238(4) -0.100(7) 0.440(3) 0.015(15) Uiso 1 1 d . . . C3 C 0.2803(5) -0.1739(8) 0.3089(3) 0.0226(13) Uani 1 1 d . . . H3B H 0.357(5) -0.164(6) 0.295(3) 0.019(14) Uiso 1 1 d . . . H3A H 0.260(4) -0.106(6) 0.313(3) 0.000(14) Uiso 1 1 d . . . C1 C 0.2326(4) -0.2558(7) 0.5076(3) 0.0198(13) Uani 1 1 d . . . H1B H 0.240(4) -0.210(6) 0.553(3) 0.019(15) Uiso 1 1 d . . . H1A H 0.257(6) -0.344(8) 0.512(4) 0.033(19) Uiso 1 1 d . . . C4 C 0.2289(4) -0.2423(7) 0.2427(3) 0.0213(13) Uani 1 1 d . . . H4B H 0.251(4) -0.188(6) 0.197(3) 0.009(13) Uiso 1 1 d . . . H4A H 0.264(4) -0.331(6) 0.233(3) 0.000(12) Uiso 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 I1 0.0127(2) 0.0223(3) 0.0145(2) -0.00015(12) 0.00036(12) 0.00041(13) I2 0.0205(3) 0.0239(3) 0.0155(2) 0.00089(13) 0.00044(12) 0.00486(15) N2 0.017(2) 0.028(3) 0.016(3) 0.001(2) -0.0006(18) -0.001(2) N1 0.017(2) 0.026(3) 0.016(2) -0.001(2) -0.0001(19) -0.002(2) N3 0.015(2) 0.023(3) 0.018(2) -0.001(2) -0.0013(19) -0.003(2) C2 0.021(3) 0.029(4) 0.019(3) -0.002(2) 0.002(2) -0.005(2) C3 0.013(3) 0.026(4) 0.028(3) -0.001(3) 0.000(2) -0.001(3) C1 0.012(3) 0.032(4) 0.016(3) 0.005(3) -0.003(2) -0.002(3) C4 0.016(3) 0.030(4) 0.018(3) -0.002(3) 0.004(2) 0.007(2) _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 N2 C3 1.464(7) . ? N2 C2 1.465(7) . ? N1 C1 1.501(7) . ? N3 C4 1.506(6) . ? C2 C1 1.529(8) . ? C3 C4 1.517(8) . ? 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 C3 N2 C2 113.4(5) . . ? N2 C2 C1 110.2(5) . . ? N2 C3 C4 110.5(5) . . ? N1 C1 C2 109.3(5) . . ? N3 C4 C3 108.8(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 C3 N2 C2 C1 169.6(5) . . . . ? C2 N2 C3 C4 -166.3(5) . . . . ? N2 C2 C1 N1 -59.5(7) . . . . ? N2 C3 C4 N3 60.3(7) . . . . ? 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 N2 H21 I2 0.95(8) 3.04(7) 3.866(5) 146(5) 8_655 N1 H13 I1 1.03(7) 2.51(7) 3.538(5) 174(5) 4_446 N1 H12 I1 0.79(7) 2.90(7) 3.634(5) 154(6) 8_655 N1 H11 I2 1.02(8) 2.68(7) 3.573(5) 145(5) 5_556 N1 H11 I2 1.02(8) 3.23(7) 3.805(5) 117(5) . N3 H33 I1 1.02(6) 2.68(6) 3.616(5) 153(4) 8_655 N3 H32 I1 0.88(8) 2.94(8) 3.604(5) 134(5) 6_556 N3 H32 I2 0.88(8) 3.18(7) 3.711(5) 121(5) . N3 H31 I2 0.74(6) 2.83(7) 3.547(5) 166(6) 3_545 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.222 _refine_diff_density_min -1.618 _refine_diff_density_rms 0.238 #===END data_1e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H16 Cl3 N3' _chemical_formula_weight 212.55 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pmmn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z' 'x+1/2, -y, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z' '-x-1/2, y, z' _cell_length_a 5.1016(7) _cell_length_b 21.343(3) _cell_length_c 4.7440(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 516.54(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min 0.7884 _exptl_absorpt_correction_T_max 0.8513 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3561 _diffrn_reflns_av_R_equivalents 0.046 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 4.11 _diffrn_reflns_theta_max 27.47 _reflns_number_total 662 _reflns_number_gt 557 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0000P)^2^+0.1996P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 662 _refine_ls_number_parameters 44 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0672 _refine_ls_wR_factor_gt 0.0640 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _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 Cl1 Cl -0.2500 0.2500 -0.04108(16) 0.0141(2) Uani 1 4 d S . . Cl2 Cl 0.7500 0.43595(3) 0.82338(12) 0.0174(2) Uani 1 2 d S . . N1 N 0.2500 0.2500 0.3163(6) 0.0108(6) Uani 1 4 d S . . H11 H 0.096(6) 0.2500 0.201(6) 0.033(8) Uiso 1 2 d S . . N2 N 0.2500 0.42482(10) 0.4280(5) 0.0153(5) Uani 1 2 d S . . H22 H 0.2500 0.4577(19) 0.307(7) 0.047(10) Uiso 1 2 d S . . H21 H 0.392(4) 0.4292(9) 0.538(4) 0.025(6) Uiso 1 1 d . . . C1 C 0.2500 0.30965(10) 0.4835(5) 0.0123(5) Uani 1 2 d S . . H1A H 0.4075 0.3117 0.6050 0.015 Uiso 0.50 1 calc PR . . H1B H 0.0925 0.3117 0.6050 0.015 Uiso 0.50 1 calc PR . . C2 C 0.2500 0.36412(12) 0.2730(5) 0.0141(5) Uani 1 2 d S . . H2A H 0.4072 0.3615 0.1512 0.017 Uiso 0.50 1 calc PR . . H2B H 0.0928 0.3615 0.1512 0.017 Uiso 0.50 1 calc PR . . 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 Cl1 0.0104(4) 0.0173(4) 0.0148(4) 0.000 0.000 0.000 Cl2 0.0169(3) 0.0138(3) 0.0214(3) 0.0040(2) 0.000 0.000 N1 0.0100(13) 0.0114(15) 0.0111(13) 0.000 0.000 0.000 N2 0.0161(12) 0.0096(11) 0.0203(11) 0.0022(9) 0.000 0.000 C1 0.0143(12) 0.0098(12) 0.0129(11) 0.0006(8) 0.000 0.000 C2 0.0179(12) 0.0105(12) 0.0138(11) 0.0006(8) 0.000 0.000 _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 C1 1.500(3) . ? N1 C1 1.500(3) 2 ? N2 C2 1.490(3) . ? C1 C2 1.532(3) . ? 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 C1 N1 C1 116.1(2) . 2 ? N1 C1 C2 107.41(18) . . ? N2 C2 C1 109.77(19) . . ? 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 C1 C2 180.0 2 . . . ? N1 C1 C2 N2 180.0 . . . . ? 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 H11 Cl1 0.96(3) 2.11(3) 3.0627(16) 178(2) . N2 H22 Cl2 0.91(4) 2.35(4) 3.202(2) 156(3) 5_666 N2 H21 Cl2 0.90(2) 2.28(2) 3.1750(14) 177.5(18) . N1 H11 Cl1 0.96(3) 2.11(3) 3.0627(16) 178(2) . N2 H22 Cl2 0.91(4) 2.35(4) 3.202(2) 156(3) 5_666 N2 H21 Cl2 0.90(2) 2.28(2) 3.1750(14) 177.5(18) . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.395 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.064 #===END data_1f _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H16 Br3 N3' _chemical_formula_weight 345.93 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 Monoclinic P _symmetry_space_group_name_H-M P21/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 6.2094(12) _cell_length_b 19.674(4) _cell_length_c 9.0026(18) _cell_angle_alpha 90.00 _cell_angle_beta 93.39(3) _cell_angle_gamma 90.00 _cell_volume 1097.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 10.972 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7068 _diffrn_reflns_av_R_equivalents 0.068 _diffrn_reflns_av_sigmaI/netI 0.0843 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2145 _reflns_number_gt 1823 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0732P)^2^+2.9465P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0022(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 2145 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1369 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.514 _refine_ls_shift/su_mean 0.009 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 0.33714(10) 0.46918(4) 0.79949(7) 0.0179(3) Uani 1 1 d . . . Br2 Br 1.32154(9) 0.84308(4) 1.03900(7) 0.0185(3) Uani 1 1 d . . . Br3 Br 1.84451(9) 0.73947(4) 1.25049(6) 0.0169(2) Uani 1 1 d . . . N1 N 0.8149(8) 0.6132(3) 0.5110(6) 0.0186(13) Uani 1 1 d . . . H13 H 0.6994 0.6509 0.5238 0.000(15) Uiso 1 1 d R . . H12 H 0.9455 0.6227 0.4969 0.06(3) Uiso 1 1 d R . . H11 H 0.7602 0.5985 0.4096 0.013(18) Uiso 1 1 d R . . N2 N 1.0481(8) 0.6077(3) 0.8225(5) 0.0158(12) Uani 1 1 d . . . H22 H 1.1303 0.5682 0.7938 0.02(2) Uiso 1 1 d R . . H21 H 1.0687 0.6515 0.7584 0.010(17) Uiso 1 1 d R . . N3 N 1.3438(8) 0.6774(3) 1.1669(5) 0.0159(12) Uani 1 1 d . . . H33 H 1.4885 0.7014 1.1763 2(5) Uiso 1 1 d R . . H32 H 1.3600 0.6352 1.2118 0.000(14) Uiso 1 1 d R . . H31 H 1.3050 0.7187 1.1630 0.05(3) Uiso 1 1 d R . . C1 C 0.8020(10) 0.5565(4) 0.6220(7) 0.0194(15) Uani 1 1 d . . . H1B H 0.9173 0.5231 0.6053 0.023 Uiso 1 1 calc R . . H1A H 0.6616 0.5330 0.6050 0.023 Uiso 1 1 calc R . . C2 C 0.8248(9) 0.5807(4) 0.7821(7) 0.0179(15) Uani 1 1 d . . . H2B H 0.7175 0.6169 0.7970 0.021 Uiso 1 1 calc R . . H2A H 0.7938 0.5425 0.8490 0.021 Uiso 1 1 calc R . . C3 C 1.0840(10) 0.6257(4) 0.9832(6) 0.0178(15) Uani 1 1 d . . . H3B H 1.0742 0.5843 1.0451 0.021 Uiso 1 1 calc R . . H3A H 0.9722 0.6581 1.0121 0.021 Uiso 1 1 calc R . . C4 C 1.3052(10) 0.6573(4) 1.0079(7) 0.0190(16) Uani 1 1 d . . . H4B H 1.4167 0.6243 0.9808 0.023 Uiso 1 1 calc R . . H4A H 1.3158 0.6978 0.9435 0.023 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 Br1 0.0172(4) 0.0236(5) 0.0130(4) -0.0009(2) 0.0007(2) 0.0000(2) Br2 0.0092(4) 0.0329(5) 0.0135(4) -0.0027(2) 0.0026(2) -0.0004(2) Br3 0.0130(4) 0.0238(5) 0.0139(4) 0.0003(2) 0.0015(2) -0.0013(2) N1 0.012(3) 0.033(4) 0.011(2) -0.001(2) 0.0030(19) 0.002(2) N2 0.011(2) 0.029(4) 0.007(2) -0.003(2) 0.0005(18) 0.000(2) N3 0.019(3) 0.017(4) 0.011(2) 0.000(2) -0.004(2) 0.001(2) C1 0.011(3) 0.033(5) 0.014(3) -0.004(3) -0.002(2) -0.004(3) C2 0.013(3) 0.029(5) 0.012(3) 0.000(3) 0.002(2) -0.002(3) C3 0.014(3) 0.033(5) 0.006(3) 0.000(3) 0.001(2) -0.004(3) C4 0.017(3) 0.029(5) 0.011(3) -0.001(3) -0.001(2) -0.002(3) _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 C1 1.503(9) . ? N2 C3 1.493(7) . ? N2 C2 1.509(8) . ? N3 C4 1.490(8) . ? C1 C2 1.517(8) . ? C3 C4 1.513(9) . ? 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 C3 N2 C2 113.5(5) . . ? N1 C1 C2 113.1(6) . . ? N2 C2 C1 111.9(5) . . ? N2 C3 C4 108.8(5) . . ? N3 C4 C3 110.1(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 C3 N2 C2 C1 -174.3(6) . . . . ? N1 C1 C2 N2 -67.1(7) . . . . ? C2 N2 C3 C4 -175.4(6) . . . . ? N2 C3 C4 N3 178.6(6) . . . . ? 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 H13 Br2 1.04 2.36 3.206(5) 137.2 4_475 N1 H13 Br3 1.04 3.07 3.610(6) 113.3 4_475 N1 H12 Br2 0.85 2.44 3.257(5) 162.2 4_575 N1 H11 Br1 1.00 2.36 3.320(6) 162.3 3_666 N2 H22 Br1 0.97 2.33 3.276(6) 163.4 1_655 N2 H21 Br3 1.05 2.56 3.311(6) 128.4 4_475 N2 H21 Br2 1.05 2.60 3.293(5) 123.4 4_575 N3 H33 Br3 1.01 2.39 3.384(5) 165.7 . N3 H32 Br1 0.93 2.79 3.502(6) 134.4 3_767 N3 H31 Br2 0.85 2.69 3.457(7) 150.5 . N3 H31 Br3 0.85 3.04 3.456(5) 112.8 1_455 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.196 _refine_diff_density_min -1.406 _refine_diff_density_rms 0.272 #===END data_2a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H19 Br2 N3 O' _chemical_formula_weight 297.05 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic P _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.8037(10) _cell_length_b 11.005(2) _cell_length_c 10.871(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.63(3) _cell_angle_gamma 90.00 _cell_volume 571.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour white-yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.719 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 294 _exptl_absorpt_coefficient_mu 7.050 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4550 _diffrn_reflns_av_R_equivalents 0.106 _diffrn_reflns_av_sigmaI/netI 0.1674 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.15 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2091 _reflns_number_gt 1992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0000P)^2^+1.8978P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.047(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(4) _refine_ls_number_reflns 2091 _refine_ls_number_parameters 114 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.1667 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.045 _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 Br1 Br 0.81979(17) 0.26094(7) 0.78386(7) 0.0162(3) Uani 1 1 d . . . Br2 Br 1.04536(15) 0.93550(7) 0.61284(7) 0.0141(3) Uani 1 1 d . . . O1 O 0.1103(13) 0.2722(7) 1.0759(6) 0.0186(14) Uani 1 1 d . . . H101 H 0.0014 0.2514 1.0135 0.08(7) Uiso 1 1 d R . . N1 N 0.7174(17) 0.7157(8) 0.4343(8) 0.0170(17) Uani 1 1 d . . . H13 H 0.8285 0.6524 0.4165 0.020 Uiso 1 1 calc R . . H12 H 0.8253 0.7766 0.4699 0.020 Uiso 1 1 calc R . . H11 H 0.6219 0.7434 0.3634 0.020 Uiso 1 1 calc R . . N2 N 0.6174(16) 0.5603(7) 0.8556(7) 0.0137(16) Uani 1 1 d . . . H21 H 0.7086 0.4890 0.8293 0.016 Uiso 1 1 d R . . N3 N 0.4133(17) 0.4714(8) 1.1689(8) 0.0152(17) Uani 1 1 d . . . H33 H 0.3095 0.4043 1.1469 0.018 Uiso 1 1 calc R . . H32 H 0.2975 0.5353 1.1792 0.018 Uiso 1 1 calc R . . H31 H 0.5208 0.4568 1.2411 0.018 Uiso 1 1 calc R . . C1 C 0.513(2) 0.6739(10) 0.5225(9) 0.018(2) Uani 1 1 d . . . H1B H 0.3956 0.6076 0.4838 0.022 Uiso 1 1 calc R . . H1A H 0.3879 0.7422 0.5397 0.022 Uiso 1 1 calc R . . C2 C 0.667(2) 0.6287(10) 0.6440(9) 0.0150(18) Uani 1 1 d . . . H2B H 0.73(3) 0.568(14) 0.628(12) 0.018 Uiso 1 1 d . . . H2A H 0.80(3) 0.692(12) 0.683(11) 0.018 Uiso 1 1 d . . . C3 C 0.4614(19) 0.5939(10) 0.7370(8) 0.0164(18) Uani 1 1 d . . . H3B H 0.36(3) 0.513(12) 0.696(11) 0.020 Uiso 1 1 d . . . H3A H 0.37(3) 0.649(13) 0.750(12) 0.020 Uiso 1 1 d . . . C4 C 0.423(2) 0.5308(9) 0.9497(9) 0.0157(19) Uani 1 1 d . . . H4B H 0.3041 0.4606 0.9219 0.019 Uiso 1 1 calc R . . H4A H 0.2997 0.6011 0.9615 0.019 Uiso 1 1 calc R . . C5 C 0.596(2) 0.5005(10) 1.0704(8) 0.015(2) Uani 1 1 d . . . H5B H 0.7186 0.4301 1.0577 0.018 Uiso 1 1 calc R . . H5A H 0.7173 0.5706 1.0965 0.018 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 Br1 0.0184(5) 0.0133(5) 0.0163(5) -0.0013(3) -0.0009(3) 0.0008(4) Br2 0.0145(5) 0.0110(5) 0.0170(5) -0.0011(3) 0.0014(3) -0.0004(3) O1 0.018(3) 0.015(3) 0.022(3) -0.004(3) 0.000(3) 0.002(3) N1 0.019(4) 0.017(4) 0.015(4) 0.002(3) -0.003(3) 0.001(3) N2 0.015(4) 0.013(4) 0.014(4) 0.002(3) 0.003(3) 0.002(3) N3 0.013(4) 0.015(4) 0.017(4) -0.001(3) -0.004(3) -0.003(3) C1 0.012(4) 0.023(6) 0.020(5) -0.007(4) 0.003(4) -0.002(4) C2 0.019(5) 0.011(5) 0.014(4) -0.002(4) 0.000(3) -0.004(4) C3 0.020(4) 0.015(5) 0.014(4) -0.004(4) 0.001(3) 0.004(4) C4 0.015(4) 0.013(5) 0.020(5) 0.002(4) 0.007(4) -0.004(4) C5 0.020(4) 0.020(5) 0.007(4) -0.001(4) 0.008(3) 0.001(4) _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 C1 1.510(12) . ? N2 C3 1.474(12) . ? N2 C4 1.487(11) . ? N3 C5 1.486(12) . ? C1 C2 1.533(14) . ? C2 C3 1.529(13) . ? C4 C5 1.521(13) . ? 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 C3 N2 C4 110.9(8) . . ? N1 C1 C2 110.9(8) . . ? C3 C2 C1 111.2(8) . . ? N2 C3 C2 109.6(8) . . ? N2 C4 C5 108.3(7) . . ? N3 C5 C4 110.9(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 N1 C1 C2 C3 176.3(8) . . . . ? C4 N2 C3 C2 177.7(8) . . . . ? C1 C2 C3 N2 -175.5(8) . . . . ? C3 N2 C4 C5 -178.4(8) . . . . ? N2 C4 C5 N3 179.4(8) . . . . ? 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 O1 H101 Br1 0.85 2.56 3.343(7) 153.3 1_455 N1 H13 Br2 0.91 2.49 3.345(9) 156.4 2_746 N1 H12 Br2 0.91 2.50 3.391(9) 165.1 . N1 H11 Br1 0.91 2.54 3.366(8) 151.8 2_656 N2 H21 Br1 0.96 2.62 3.543(8) 161.7 . N3 H33 O1 0.91 1.87 2.768(11) 170.7 . N3 H32 Br1 0.91 2.59 3.433(9) 154.9 2_657 N3 H31 Br2 0.91 2.50 3.367(8) 158.4 2_747 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.433 _refine_diff_density_min -1.255 _refine_diff_density_rms 0.204 #===END data_3a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H12 Cl N2 O' _chemical_formula_weight 127.60 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 4.7197(9) _cell_length_b 10.658(2) _cell_length_c 13.046(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.25(3) _cell_angle_gamma 90.00 _cell_volume 655.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour pale yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.483 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7597 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1280 _reflns_number_gt 1166 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0000P)^2^+0.2493P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.024(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 1280 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0263 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0545 _refine_ls_wR_factor_gt 0.0530 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 Cl1 Cl 0.12162(6) 0.65801(3) 0.42017(2) 0.01398(13) Uani 1 1 d . . . O1 O -0.89014(19) 0.33570(9) 0.81892(7) 0.0154(2) Uani 1 1 d . . . H102 H -0.931(4) 0.3351(16) 0.7618(15) 0.029(5) Uiso 1 1 d . . . H101 H -0.802(4) 0.4072(18) 0.8288(13) 0.032(5) Uiso 1 1 d . . . N1 N -0.3801(2) 0.62867(11) 0.59430(8) 0.0121(2) Uani 1 1 d . . . H13 H -0.276(3) 0.5630(17) 0.5821(12) 0.023(4) Uiso 1 1 d . . . H12 H -0.486(4) 0.6460(15) 0.5351(13) 0.028(4) Uiso 1 1 d . . . H11 H -0.265(3) 0.6952(16) 0.6119(11) 0.023(4) Uiso 1 1 d . . . N2 N -0.5784(2) 0.54881(10) 0.86267(7) 0.0113(2) Uani 1 1 d . . . H21 H -0.663(3) 0.6152(15) 0.8745(10) 0.010(3) Uiso 1 1 d . . . C1 C -0.5733(2) 0.60412(13) 0.67958(9) 0.0125(3) Uani 1 1 d . . . H1B H -0.680(3) 0.6794(15) 0.6870(11) 0.017(4) Uiso 1 1 d . . . H1A H -0.698(3) 0.5351(15) 0.6589(11) 0.016(3) Uiso 1 1 d . . . C2 C -0.3958(2) 0.57095(13) 0.77685(9) 0.0134(3) Uani 1 1 d . . . H2B H -0.290(3) 0.4922(15) 0.7646(11) 0.021(4) Uiso 1 1 d . . . H2A H -0.257(3) 0.6386(15) 0.7926(11) 0.018(4) Uiso 1 1 d . . . C3 C -0.4053(2) 0.51183(12) 0.95581(8) 0.0127(3) Uani 1 1 d . . . H3B H -0.305(3) 0.4347(14) 0.9387(10) 0.013(3) Uiso 1 1 d . . . H3A H -0.269(3) 0.5783(15) 0.9763(10) 0.017(3) Uiso 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 Cl1 0.01610(18) 0.01327(19) 0.01217(18) 0.00024(11) -0.00271(11) 0.00004(11) O1 0.0201(5) 0.0129(5) 0.0126(5) 0.0004(3) -0.0038(4) -0.0011(4) N1 0.0134(5) 0.0129(6) 0.0098(5) 0.0004(4) -0.0009(4) 0.0001(4) N2 0.0128(5) 0.0113(6) 0.0099(5) 0.0002(4) 0.0004(4) 0.0028(4) C1 0.0117(6) 0.0148(7) 0.0110(6) 0.0011(5) 0.0003(4) -0.0001(5) C2 0.0120(6) 0.0171(7) 0.0110(6) 0.0022(5) 0.0004(4) 0.0002(5) C3 0.0122(6) 0.0157(7) 0.0101(6) 0.0002(5) -0.0009(5) 0.0005(5) _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 C1 1.5008(15) . ? N2 C2 1.4702(15) . ? N2 C3 1.4786(15) . ? C1 C2 1.5219(16) . ? C3 C3 1.519(2) 3_467 ? 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 C2 N2 C3 110.38(9) . . ? N1 C1 C2 109.26(10) . . ? N2 C2 C1 110.71(10) . . ? N2 C3 C3 110.27(12) . 3_467 ? 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 C3 N2 C2 C1 177.80(10) . . . . ? N1 C1 C2 N2 178.83(10) . . . . ? C2 N2 C3 C3 -179.63(13) . . . 3_467 ? 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 O1 H102 Cl1 0.758(19) 2.49(2) 3.2466(13) 173.0(17) 3_466 O1 H101 N2 0.87(2) 1.88(2) 2.7486(15) 172.0(17) . N1 H13 Cl1 0.874(18) 2.467(18) 3.2995(13) 159.4(13) 3_566 N1 H12 Cl1 0.914(18) 2.321(19) 3.1910(15) 159.1(14) 1_455 N1 H11 O1 0.914(17) 1.876(17) 2.7592(15) 161.9(13) 2_456 N2 H21 Cl1 0.832(16) 2.701(16) 3.5287(13) 173.2(12) 4_476 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.297 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.047 #===END data_3b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H12 Br N2 O' _chemical_formula_weight 172.06 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 Monoclinic _symmetry_space_group_name_H-M P21/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 4.7413(9) _cell_length_b 10.935(2) _cell_length_c 13.315(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.77(3) _cell_angle_gamma 90.00 _cell_volume 690.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 5.863 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9018 _diffrn_reflns_av_R_equivalents 0.076 _diffrn_reflns_av_sigmaI/netI 0.0795 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1348 _reflns_number_gt 1255 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0000P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 1348 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.530 _refine_ls_shift/su_mean 0.005 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 0.38562(5) 0.161133(18) 0.079917(15) 0.01595(18) Uani 1 1 d . . . O1 O 0.3829(5) 0.66530(18) 0.17724(17) 0.0193(5) Uani 1 1 d . . . H102 H 0.431(9) 0.662(3) 0.242(3) 0.036(11) Uiso 1 1 d . . . H101 H 0.319(8) 0.617(3) 0.169(3) 0.025(12) Uiso 1 1 d . . . N1 N -0.1145(5) 0.3694(2) 0.39837(15) 0.0158(4) Uani 1 1 d . . . H13 H -0.017(9) 0.356(3) 0.457(3) 0.035(10) Uiso 1 1 d . . . H12 H -0.226(7) 0.291(3) 0.386(2) 0.028(7) Uiso 1 1 d . . . H11 H -0.203(6) 0.425(3) 0.4124(19) 0.011(7) Uiso 1 1 d . . . N2 N 0.0775(4) 0.4549(2) 0.13449(13) 0.0141(4) Uani 1 1 d . . . H21 H 0.174(6) 0.389(3) 0.1228(17) 0.007(6) Uiso 1 1 d . . . C3 C -0.0944(5) 0.4874(2) 0.04419(18) 0.0162(5) Uani 1 1 d . . . H3B H -0.212(7) 0.419(3) 0.028(2) 0.029(7) Uiso 1 1 d . . . H3A H -0.197(5) 0.559(2) 0.0599(16) 0.007(6) Uiso 1 1 d . . . C1 C 0.0752(5) 0.3975(2) 0.31340(17) 0.0152(5) Uani 1 1 d . . . H1B H 0.184(8) 0.330(2) 0.309(2) 0.017(8) Uiso 1 1 d . . . H1A H 0.183(6) 0.456(2) 0.3357(19) 0.011(6) Uiso 1 1 d . . . C2 C -0.1049(5) 0.4289(2) 0.21990(16) 0.0159(5) Uani 1 1 d . . . H2B H -0.244(6) 0.357(2) 0.2055(18) 0.000(5) Uiso 1 1 d . . . H2A H -0.218(6) 0.502(2) 0.231(2) 0.016(7) Uiso 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 0.0195(2) 0.0147(3) 0.0134(2) -0.00057(6) -0.00334(13) 0.00041(8) O1 0.0237(12) 0.0176(12) 0.0163(11) -0.0006(6) -0.0058(8) -0.0029(8) N1 0.0191(12) 0.0159(11) 0.0124(11) 0.0005(9) -0.0012(9) 0.0004(10) N2 0.0176(11) 0.0145(10) 0.0101(10) 0.0009(7) 0.0000(8) 0.0022(9) C3 0.0164(13) 0.0195(13) 0.0125(12) 0.0009(8) -0.0020(9) 0.0027(11) C1 0.0158(12) 0.0150(13) 0.0146(12) 0.0003(8) -0.0007(10) -0.0004(11) C2 0.0152(12) 0.0205(13) 0.0119(11) 0.0019(8) -0.0028(9) 0.0027(11) _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 C1 1.499(3) . ? N2 C3 1.475(3) . ? N2 C2 1.477(3) . ? C3 C3 1.525(5) 3_565 ? C1 C2 1.527(3) . ? 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 C3 N2 C2 110.60(18) . . ? N2 C3 C3 110.5(2) . 3_565 ? N1 C1 C2 109.2(2) . . ? N2 C2 C1 110.2(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 C2 N2 C3 C3 -179.2(2) . . . 3_565 ? C3 N2 C2 C1 -179.0(2) . . . . ? N1 C1 C2 N2 -179.0(2) . . . . ? 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 O1 H102 Br1 0.88(4) 2.50(5) 3.383(2) 174(4) 2_655 O1 H101 N2 0.62(4) 2.15(4) 2.769(3) 176(4) . N1 H13 Br1 0.91(4) 2.48(5) 3.350(2) 160(3) 4_566 N1 H12 O1 1.02(3) 1.77(3) 2.745(3) 160(3) 2_545 N1 H11 Br1 0.77(3) 2.73(3) 3.455(3) 160(2) 2 N2 H21 Br1 0.87(3) 2.76(3) 3.612(2) 170(2) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.771 _refine_diff_density_min -0.780 _refine_diff_density_rms 0.107 #===END data_3c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H12 I N2 O' _chemical_formula_weight 219.05 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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 4.8139(10) _cell_length_b 11.418(2) _cell_length_c 13.689(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.48(3) _cell_angle_gamma 90.00 _cell_volume 752.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.934 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 4.170 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10258 _diffrn_reflns_av_R_equivalents 0.053 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 25.97 _reflns_number_total 1457 _reflns_number_gt 1271 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0000P)^2^+0.0215P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0023(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 1457 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0182 _refine_ls_wR_factor_ref 0.0432 _refine_ls_wR_factor_gt 0.0417 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.002 _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 I1 I 0.11924(3) 0.836007(14) 0.081385(11) 0.01748(9) Uani 1 1 d . . . O1 O 0.8637(4) 0.83429(19) 0.32726(13) 0.0222(4) Uani 1 1 d . . . H102 H 0.8910 0.8369 0.2665 0.027(9) Uiso 1 1 d R . . H101 H 0.8029 0.8871 0.3354 0.070(19) Uiso 1 1 d R . . N1 N 0.4239(5) 0.5384(2) 0.13081(15) 0.0158(5) Uani 1 1 d . . . H11 H 0.322(7) 0.593(3) 0.116(2) 0.021(8) Uiso 1 1 d . . . N2 N 0.6075(5) 0.6324(2) 0.38796(17) 0.0172(5) Uani 1 1 d . . . H23 H 0.517(7) 0.650(3) 0.435(3) 0.022(9) Uiso 1 1 d . . . H22 H 0.715(7) 0.577(3) 0.408(2) 0.018(8) Uiso 1 1 d . . . H21 H 0.721(9) 0.688(4) 0.374(3) 0.037(10) Uiso 1 1 d . . . C1 C 0.5952(5) 0.5142(3) 0.04338(17) 0.0183(5) Uani 1 1 d . . . H1B H 0.7282 0.4320 0.0653 0.027(8) Uiso 1 1 d R . . H1A H 0.7291 0.5977 0.0215 0.041(10) Uiso 1 1 d R . . C2 C 0.6025(6) 0.5723(3) 0.21425(18) 0.0174(5) Uani 1 1 d . . . H2B H 0.720(7) 0.638(3) 0.201(2) 0.020(8) Uiso 1 1 d . . . H2A H 0.716(6) 0.515(3) 0.2281(19) 0.014(7) Uiso 1 1 d . . . C3 C 0.4241(6) 0.5987(3) 0.30373(18) 0.0172(6) Uani 1 1 d . . . H3B H 0.333(6) 0.532(3) 0.320(2) 0.016(7) Uiso 1 1 d . . . H3A H 0.302(8) 0.661(3) 0.291(3) 0.027(9) Uiso 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 I1 0.02097(12) 0.01629(13) 0.01522(12) 0.00099(7) 0.00289(7) 0.00055(7) O1 0.0317(11) 0.0177(11) 0.0172(10) 0.0011(8) 0.0064(8) 0.0014(9) N1 0.0185(11) 0.0156(12) 0.0132(10) -0.0001(9) -0.0014(8) 0.0036(9) N2 0.0189(12) 0.0200(14) 0.0128(11) -0.0003(10) 0.0025(10) -0.0008(11) C1 0.0188(12) 0.0232(15) 0.0128(11) -0.0029(11) 0.0001(10) -0.0008(11) C2 0.0195(14) 0.0192(15) 0.0137(12) -0.0017(11) 0.0008(10) -0.0018(12) C3 0.0197(14) 0.0192(15) 0.0128(12) -0.0015(11) 0.0022(10) -0.0020(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 C2 1.475(3) . ? N1 C1 1.485(3) . ? N2 C3 1.497(3) . ? C1 C1 1.529(5) 3_665 ? C2 C3 1.532(4) . ? 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 C2 N1 C1 110.42(19) . . ? N1 C1 C1 109.4(2) . 3_665 ? N1 C2 C3 110.1(2) . . ? N2 C3 C2 109.6(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 C2 N1 C1 C1 -177.0(3) . . . 3_665 ? C1 N1 C2 C3 179.2(2) . . . . ? N1 C2 C3 N2 179.7(2) . . . . ? 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 O1 H102 I1 0.84 2.77 3.593(2) 165.4 1_655 O1 H101 N1 0.68 2.10 2.774(3) 172.9 2_655 N1 H11 I1 0.82(3) 2.98(4) 3.760(2) 161(3) . N2 H23 I1 0.80(4) 2.79(4) 3.574(3) 166(3) 4_576 N2 H22 I1 0.86(3) 2.87(4) 3.654(3) 152(3) 2_645 N2 H22 I1 0.86(3) 3.21(3) 3.619(3) 112(2) 4_676 N2 H21 O1 0.86(4) 1.92(4) 2.746(3) 161(4) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.444 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.088 #===END data_3d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H24 Br4 N4 O' _chemical_formula_weight 487.92 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 Orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 14.286(3) _cell_length_b 16.187(3) _cell_length_c 14.162(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3274.9(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.975 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1880 _exptl_absorpt_coefficient_mu 9.819 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type scalepack _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13121 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2999 _reflns_number_gt 2925 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0689P)^2^+14.9962P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00011(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.58(3) _refine_ls_number_reflns 2999 _refine_ls_number_parameters 142 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1088 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.006 _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 0.15490(4) 0.01976(4) 0.25843(5) 0.01285(19) Uani 1 1 d . . . Br2 Br -0.03109(4) -0.30029(4) -0.09188(5) 0.01286(19) Uani 1 1 d . . . Br3 Br 0.0000 0.0000 -0.00035(7) 0.0121(2) Uani 1 2 d S . . Br4 Br 0.5000 0.0000 0.13191(8) 0.0169(2) Uani 1 2 d S . . Br5 Br 0.20178(4) -0.25087(4) 0.12620(5) 0.01411(19) Uani 1 1 d . . . O1 O 0.2125(6) 0.1660(5) -0.1352(5) 0.048(2) Uani 1 1 d . . . H101 H 0.162(9) 0.202(8) -0.139(8) 0.05(3) Uiso 1 1 d . . . N1 N 0.3525(4) 0.0873(4) -0.0120(4) 0.0144(12) Uani 1 1 d . . . H13 H 0.3452 0.0832 -0.0756 0.017 Uiso 1 1 calc R . . H12 H 0.4073 0.0629 0.0052 0.017 Uiso 1 1 calc R . . H11 H 0.3536 0.1415 0.0050 0.017 Uiso 1 1 calc R . . N2 N 0.2065(4) -0.0509(4) -0.0841(4) 0.0129(12) Uani 1 1 d . . . H22 H 0.2355 -0.0214 -0.1313 0.016 Uiso 1 1 calc R . . H21 H 0.1488 -0.0274 -0.0737 0.016 Uiso 1 1 calc R . . N3 N 0.1158(4) -0.2227(4) -0.2388(4) 0.0127(11) Uani 1 1 d . . . H32 H 0.0887 -0.2537 -0.1916 0.015 Uiso 1 1 calc R . . H31 H 0.1728 -0.2460 -0.2529 0.015 Uiso 1 1 calc R . . N4 N -0.0224(4) -0.3638(4) -0.3163(4) 0.0135(12) Uani 1 1 d . . . H43 H -0.0810 -0.3440 -0.3273 0.016 Uiso 1 1 calc R . . H42 H -0.0106 -0.3630 -0.2532 0.016 Uiso 1 1 calc R . . H41 H -0.0182 -0.4166 -0.3380 0.016 Uiso 1 1 calc R . . C1 C 0.2731(5) 0.0452(5) 0.0363(5) 0.0157(15) Uani 1 1 d . . . H1B H 0.2143 0.0752 0.0224 0.019 Uiso 1 1 calc R . . H1A H 0.2832 0.0467 0.1054 0.019 Uiso 1 1 calc R . . C2 C 0.2636(5) -0.0443(4) 0.0042(5) 0.0164(14) Uani 1 1 d . . . H2B H 0.3266 -0.0678 -0.0072 0.020 Uiso 1 1 calc R . . H2A H 0.2335 -0.0770 0.0549 0.020 Uiso 1 1 calc R . . C3 C 0.1932(5) -0.1383(5) -0.1162(4) 0.0127(14) Uani 1 1 d . . . H3B H 0.1634 -0.1713 -0.0657 0.015 Uiso 1 1 calc R . . H3A H 0.2545 -0.1635 -0.1316 0.015 Uiso 1 1 calc R . . C4 C 0.1308(5) -0.1369(5) -0.2039(5) 0.0162(14) Uani 1 1 d . . . H4B H 0.0698 -0.1114 -0.1881 0.019 Uiso 1 1 calc R . . H4A H 0.1607 -0.1033 -0.2539 0.019 Uiso 1 1 calc R . . C5 C 0.0548(5) -0.2255(5) -0.3242(5) 0.0146(14) Uani 1 1 d . . . H5B H 0.0801 -0.1871 -0.3723 0.017 Uiso 1 1 calc R . . H5A H -0.0087 -0.2061 -0.3070 0.017 Uiso 1 1 calc R . . C6 C 0.0478(5) -0.3108(4) -0.3664(5) 0.0136(14) Uani 1 1 d . . . H6B H 0.0298 -0.3061 -0.4337 0.016 Uiso 1 1 calc R . . H6A H 0.1099 -0.3378 -0.3635 0.016 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 Br1 0.0117(3) 0.0180(4) 0.0088(3) 0.0005(2) -0.0029(2) 0.0010(2) Br2 0.0111(3) 0.0186(4) 0.0089(3) -0.0004(3) 0.0008(2) 0.0016(2) Br3 0.0086(4) 0.0171(5) 0.0104(4) 0.000 0.000 0.0010(3) Br4 0.0149(5) 0.0176(5) 0.0181(5) 0.000 0.000 -0.0017(4) Br5 0.0084(3) 0.0178(4) 0.0162(3) -0.0039(3) -0.0011(3) 0.0018(2) O1 0.057(5) 0.061(5) 0.025(3) 0.003(3) 0.003(3) 0.044(4) N1 0.013(3) 0.019(3) 0.011(3) -0.003(2) 0.002(2) -0.008(2) N2 0.008(2) 0.020(3) 0.011(3) -0.006(2) 0.001(2) -0.003(2) N3 0.008(2) 0.018(3) 0.012(2) -0.001(2) 0.000(2) 0.001(2) N4 0.010(2) 0.014(3) 0.016(3) -0.001(2) -0.001(2) -0.001(2) C1 0.012(3) 0.023(4) 0.012(3) -0.005(3) 0.000(3) -0.005(3) C2 0.016(3) 0.021(4) 0.012(3) 0.003(3) -0.003(3) 0.000(3) C3 0.012(3) 0.013(4) 0.013(3) 0.004(3) 0.001(2) 0.003(2) C4 0.014(3) 0.017(4) 0.017(3) 0.001(3) -0.005(3) -0.006(3) C5 0.017(3) 0.014(4) 0.012(3) -0.002(3) -0.005(3) -0.002(3) C6 0.019(3) 0.013(3) 0.009(3) 0.003(3) 0.001(3) -0.001(3) _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 C1 1.489(9) . ? N2 C2 1.496(9) . ? N2 C3 1.498(9) . ? N3 C4 1.490(9) . ? N3 C5 1.491(9) . ? N4 C6 1.497(9) . ? C1 C2 1.524(10) . ? C3 C4 1.529(9) . ? C5 C6 1.510(10) . ? 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 C2 N2 C3 113.0(6) . . ? C4 N3 C5 112.4(6) . . ? N1 C1 C2 111.5(6) . . ? N2 C2 C1 111.4(6) . . ? N2 C3 C4 107.9(6) . . ? N3 C4 C3 109.8(6) . . ? N3 C5 C6 112.8(6) . . ? N4 C6 C5 112.4(6) . . ? 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 C3 N2 C2 C1 -178.4(5) . . . . ? N1 C1 C2 N2 -85.4(7) . . . . ? C2 N2 C3 C4 177.6(5) . . . . ? C5 N3 C4 C3 179.7(5) . . . . ? N2 C3 C4 N3 179.8(5) . . . . ? C4 N3 C5 C6 173.7(6) . . . . ? N3 C5 C6 N4 81.6(7) . . . . ? 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 O1 H101 Br2 0.93(13) 2.54(13) 3.437(7) 162(10) 2 N1 H13 O1 0.91 2.47 2.945(9) 112.8 . N1 H13 Br1 0.91 2.56 3.432(6) 159.5 8_544 N1 H12 Br4 0.91 2.45 3.254(6) 147.3 . N1 H11 Br5 0.91 2.57 3.360(6) 145.5 4 N2 H22 Br1 0.92 2.31 3.195(6) 161.2 8_544 N2 H21 Br3 0.92 2.41 3.284(5) 159.5 . N3 H32 Br2 0.92 2.34 3.210(6) 156.8 . N3 H31 Br5 0.92 2.48 3.265(6) 143.5 8_544 N4 H43 Br5 0.91 2.40 3.267(6) 158.9 6_544 N4 H42 Br2 0.91 2.52 3.342(6) 151.2 . N4 H41 Br3 0.91 2.68 3.429(6) 140.3 5_544 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.067 _refine_diff_density_min -1.236 _refine_diff_density_rms 0.239 #===END data_3e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H24 I4 N4 O' _chemical_formula_weight 675.89 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' 'I' 'I' -0.4742 1.8119 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 15.091(3) _cell_length_b 16.774(3) _cell_length_c 15.060(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3812.2(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2456 _exptl_absorpt_coefficient_mu 6.529 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 30570 _diffrn_reflns_av_R_equivalents 0.086 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 \ \ _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3527 _reflns_number_gt 3427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0303P)^2^+23.1257P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00049(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(6) _refine_ls_number_reflns 3527 _refine_ls_number_parameters 138 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0798 _refine_ls_wR_factor_gt 0.0787 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 I1 I 0.03243(3) 0.20153(3) 0.31901(4) 0.01435(13) Uani 1 1 d . . . I2 I 0.15761(3) 0.48768(3) 0.65518(3) 0.01312(13) Uani 1 1 d . . . I3 I 0.5000 0.5000 0.53881(5) 0.01735(18) Uani 1 2 d S . . I4 I 0.0000 0.5000 0.40623(5) 0.01323(17) Uani 1 2 d S . . I5 I -0.19903(3) 0.24556(3) 0.52822(4) 0.01404(13) Uani 1 1 d . . . O1 O 0.2712(6) 0.3270(5) 0.7696(5) 0.052(3) Uani 1 1 d . . . H101 H 0.2822 0.2952 0.8122 0.062 Uiso 1 1 d R . . N1 N -0.0142(4) 0.3569(4) 0.5919(5) 0.0111(13) Uani 1 1 d . . . H13 H 0.0017 0.3645 0.6495 0.013 Uiso 1 1 calc R . . H12 H -0.0680 0.3326 0.5896 0.013 Uiso 1 1 calc R . . H11 H -0.0172 0.4049 0.5638 0.013 Uiso 1 1 calc R . . N2 N 0.1197(4) 0.2227(4) 0.6704(5) 0.0123(12) Uani 1 1 d . . . H22 H 0.1736 0.2452 0.6567 0.015 Uiso 1 1 calc R . . H21 H 0.0938 0.2531 0.7141 0.015 Uiso 1 1 calc R . . N3 N 0.2058(4) 0.0568(3) 0.8183(5) 0.0103(12) Uani 1 1 d . . . H32 H 0.1506 0.0356 0.8292 0.012 Uiso 1 1 calc R . . H31 H 0.2316 0.0271 0.7739 0.012 Uiso 1 1 calc R . . N4 N 0.3482(4) -0.0789(4) 0.8852(5) 0.0151(14) Uani 1 1 d . . . H43 H 0.3996 -0.0663 0.9135 0.018 Uiso 1 1 calc R . . H42 H 0.3516 -0.0633 0.8274 0.018 Uiso 1 1 calc R . . H41 H 0.3395 -0.1325 0.8878 0.018 Uiso 1 1 calc R . . C1 C 0.0530(5) 0.3058(4) 0.5471(5) 0.0110(16) Uani 1 1 d . . . H1A H 0.1113 0.3328 0.5496 0.013 Uiso 1 1 calc R . . H1B H 0.0366 0.2997 0.4838 0.013 Uiso 1 1 calc R . . C2 C 0.0614(5) 0.2234(4) 0.5890(6) 0.0147(16) Uani 1 1 d . . . H2A H 0.0017 0.2040 0.6055 0.018 Uiso 1 1 calc R . . H2B H 0.0861 0.1860 0.5445 0.018 Uiso 1 1 calc R . . C3 C 0.1338(6) 0.1404(5) 0.7042(6) 0.0194(18) Uani 1 1 d . . . H3B H 0.1609 0.1072 0.6570 0.023 Uiso 1 1 calc R . . H3A H 0.0761 0.1164 0.7204 0.023 Uiso 1 1 calc R . . C4 C 0.1948(5) 0.1419(5) 0.7857(5) 0.0142(16) Uani 1 1 d . . . H4B H 0.2531 0.1647 0.7697 0.017 Uiso 1 1 calc R . . H4A H 0.1683 0.1753 0.8330 0.017 Uiso 1 1 calc R . . C5 C 0.2617(5) 0.0493(4) 0.9019(5) 0.0137(15) Uani 1 1 d . . . H5B H 0.3209 0.0727 0.8910 0.016 Uiso 1 1 calc R . . H5A H 0.2333 0.0796 0.9506 0.016 Uiso 1 1 calc R . . C6 C 0.2721(5) -0.0368(4) 0.9297(5) 0.0143(16) Uani 1 1 d . . . H6B H 0.2808 -0.0389 0.9948 0.017 Uiso 1 1 calc R . . H6A H 0.2166 -0.0658 0.9158 0.017 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 I1 0.0129(2) 0.0195(3) 0.0107(2) -0.0011(2) -0.0010(2) -0.00059(18) I2 0.0132(2) 0.0151(2) 0.0111(3) -0.0008(2) -0.00359(19) -0.00117(18) I3 0.0187(4) 0.0139(3) 0.0194(4) 0.000 0.000 0.0019(3) I4 0.0098(3) 0.0181(3) 0.0118(4) 0.000 0.000 -0.0021(2) I5 0.0111(2) 0.0141(2) 0.0169(3) -0.0026(2) 0.0015(2) -0.00218(18) O1 0.072(7) 0.057(5) 0.028(4) -0.006(4) -0.009(4) 0.045(5) N1 0.011(3) 0.010(3) 0.012(3) 0.003(3) -0.002(2) -0.003(2) N2 0.014(3) 0.008(3) 0.015(3) 0.000(2) -0.002(3) 0.005(3) N3 0.010(3) 0.010(3) 0.010(3) -0.003(3) 0.001(3) 0.002(2) N4 0.020(3) 0.011(3) 0.014(4) -0.002(3) 0.004(3) 0.008(3) C1 0.012(3) 0.007(3) 0.014(4) 0.000(3) 0.001(3) 0.002(3) C2 0.018(4) 0.006(3) 0.020(5) 0.001(3) -0.010(3) -0.001(3) C3 0.022(4) 0.008(3) 0.029(5) 0.005(3) 0.001(4) -0.001(3) C4 0.022(4) 0.010(3) 0.011(4) 0.002(3) -0.003(3) 0.001(3) C5 0.014(3) 0.019(4) 0.008(4) 0.000(3) -0.003(3) 0.009(3) C6 0.013(4) 0.013(3) 0.017(4) 0.002(3) 0.005(3) 0.007(3) _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 C1 1.489(9) . ? N2 C3 1.487(9) . ? N2 C2 1.508(10) . ? N3 C5 1.520(10) . ? N3 C4 1.519(9) . ? N4 C6 1.505(9) . ? C1 C2 1.525(10) . ? C3 C4 1.535(11) . ? C5 C6 1.512(10) . ? 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 C3 N2 C2 111.7(6) . . ? C5 N3 C4 113.9(6) . . ? N1 C1 C2 113.1(6) . . ? N2 C2 C1 113.1(6) . . ? N2 C3 C4 110.2(6) . . ? N3 C4 C3 108.0(6) . . ? C6 C5 N3 111.5(6) . . ? N4 C6 C5 113.8(6) . . ? 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 C3 N2 C2 C1 -174.2(6) . . . . ? N1 C1 C2 N2 -81.9(8) . . . . ? C2 N2 C3 C4 178.9(6) . . . . ? C5 N3 C4 C3 -177.4(6) . . . . ? N2 C3 C4 N3 179.1(6) . . . . ? C4 N3 C5 C6 -178.6(6) . . . . ? N3 C5 C6 N4 86.4(8) . . . . ? 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 O1 H101 I1 0.85 3.21 3.710(8) 120.1 8_545 N1 H13 I1 0.91 2.83 3.569(7) 139.3 6 N1 H12 I5 0.91 2.63 3.492(6) 159.2 . N1 H11 I4 0.91 2.87 3.691(7) 150.5 . N2 H22 O1 0.92 2.63 3.243(12) 124.3 . N2 H22 I5 0.92 2.73 3.515(7) 143.5 3 N2 H21 I1 0.92 2.59 3.449(7) 155.8 6 N3 H32 I4 0.92 2.62 3.508(6) 162.2 5_545 N3 H31 I2 0.92 2.54 3.410(7) 158.8 4_545 N4 H43 I3 0.91 2.66 3.514(7) 156.0 5_545 N4 H42 I2 0.91 2.74 3.641(7) 173.7 4_545 N4 H41 I5 0.91 2.90 3.600(7) 135.0 7_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.320 _refine_diff_density_min -1.574 _refine_diff_density_rms 0.286 #===END data_4a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H12 Cl N2' _chemical_formula_weight 123.61 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 5.5047(11) _cell_length_b 11.895(2) _cell_length_c 10.410(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.67(3) _cell_angle_gamma 90.00 _cell_volume 681.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.452 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5871 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.0588 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.98 _reflns_number_total 1330 _reflns_number_gt 1162 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0383P)^2^+0.3054P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.029(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 1330 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 Cl1 Cl 0.35921(8) 0.73875(4) 0.06739(4) 0.0174(2) Uani 1 1 d . . . N1 N 0.3384(3) 0.19758(14) 0.17885(17) 0.0152(4) Uani 1 1 d . . . H13 H 0.426(4) 0.2137(19) 0.107(2) 0.019(6) Uiso 1 1 d . . . H12 H 0.281(4) 0.127(2) 0.174(2) 0.025(6) Uiso 1 1 d . . . H11 H 0.442(5) 0.206(2) 0.248(3) 0.029(6) Uiso 1 1 d . . . N2 N -0.1047(3) 0.48392(14) 0.32818(15) 0.0146(4) Uani 1 1 d . . . H21 H -0.177(4) 0.424(2) 0.338(2) 0.016(6) Uiso 1 1 d . . . C1 C 0.1316(3) 0.27862(16) 0.1889(2) 0.0177(4) Uani 1 1 d . . . H1B H 0.044(5) 0.2608(18) 0.272(3) 0.029(6) Uiso 1 1 d . . . H1A H 0.005(4) 0.2607(17) 0.121(2) 0.018(6) Uiso 1 1 d . . . C2 C 0.2184(4) 0.39984(16) 0.17963(19) 0.0168(4) Uani 1 1 d . . . H2B H 0.346(4) 0.4140(19) 0.243(2) 0.023(6) Uiso 1 1 d . . . H2A H 0.283(4) 0.4118(18) 0.098(2) 0.017(5) Uiso 1 1 d . . . C3 C 0.0102(4) 0.48443(16) 0.19965(19) 0.0186(5) Uani 1 1 d . . . H3B H 0.079(4) 0.558(2) 0.182(2) 0.023(6) Uiso 1 1 d . . . H3A H -0.125(4) 0.4733(18) 0.135(2) 0.020(5) Uiso 1 1 d . . . C4 C 0.0698(4) 0.49189(16) 0.43740(18) 0.0163(4) Uani 1 1 d . . . H4B H 0.170(4) 0.5577(19) 0.425(2) 0.021(6) Uiso 1 1 d . . . H4A H 0.168(4) 0.4258(18) 0.4461(19) 0.015(5) Uiso 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 Cl1 0.0157(3) 0.0213(3) 0.0152(3) 0.00143(16) 0.00175(18) 0.00158(17) N1 0.0161(8) 0.0139(9) 0.0156(9) -0.0013(6) 0.0017(7) -0.0009(6) N2 0.0156(8) 0.0134(8) 0.0149(9) 0.0003(6) -0.0002(6) -0.0009(6) C1 0.0148(10) 0.0163(10) 0.0221(11) -0.0015(7) 0.0016(8) 0.0002(7) C2 0.0187(10) 0.0176(10) 0.0141(10) -0.0011(7) 0.0031(8) -0.0003(8) C3 0.0237(11) 0.0152(10) 0.0170(11) 0.0016(7) 0.0012(8) 0.0019(8) C4 0.0164(9) 0.0150(10) 0.0175(11) -0.0004(7) 0.0005(8) 0.0021(8) _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 C1 1.496(2) . ? N2 C4 1.483(2) . ? N2 C3 1.487(3) . ? C1 C2 1.522(3) . ? C2 C3 1.541(3) . ? C4 C4 1.533(4) 3_566 ? 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 C4 N2 C3 114.28(15) . . ? N1 C1 C2 111.47(15) . . ? C1 C2 C3 112.05(16) . . ? N2 C3 C2 116.36(16) . . ? N2 C4 C4 109.5(2) . 3_566 ? 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 N1 C1 C2 C3 -175.86(16) . . . . ? C4 N2 C3 C2 51.1(2) . . . . ? C1 C2 C3 N2 63.9(2) . . . . ? C3 N2 C4 C4 171.71(18) . . . 3_566 ? 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 H13 Cl1 0.91(3) 2.25(3) 3.165(2) 178(2) 3_665 N1 H12 N2 0.90(3) 1.96(3) 2.849(2) 170(2) 2_545 N1 H11 Cl1 0.92(3) 2.24(3) 3.144(2) 170(2) 2_645 N2 H21 Cl1 0.83(2) 2.61(2) 3.4185(18) 164.5(19) 2_545 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.464 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.076 #===END data_4b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H12 Br N2' _chemical_formula_weight 168.07 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 Monoclinic _symmetry_space_group_name_H-M P2(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 5.9645(12) _cell_length_b 12.573(3) _cell_length_c 9.4371(19) _cell_angle_alpha 90.00 _cell_angle_beta 100.24(3) _cell_angle_gamma 90.00 _cell_volume 696.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.6 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.603 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 5.797 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7580 _diffrn_reflns_av_R_equivalents 0.074 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1599 _reflns_number_gt 1422 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0421P)^2^+0.2476P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0047(19) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 1599 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.004 _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 0.87373(4) 0.38516(2) 0.20500(3) 0.01667(15) Uani 1 1 d . . . N1 N 1.8434(4) 0.75505(19) 0.0069(2) 0.0145(5) Uani 1 1 d . . . H13 H 1.927(6) 0.796(3) 0.080(4) 0.040(10) Uiso 1 1 d . . . H12 H 1.934(5) 0.729(2) -0.042(3) 0.010(7) Uiso 1 1 d . . . H11 H 1.767(6) 0.801(3) -0.038(4) 0.031(10) Uiso 1 1 d . . . N2 N 1.5579(4) 0.58628(18) 0.3461(2) 0.0123(4) Uani 1 1 d . . . H21 H 1.646(5) 0.541(3) 0.319(3) 0.015(8) Uiso 1 1 d . . . C1 C 1.7163(5) 0.6672(2) 0.0657(3) 0.0175(6) Uani 1 1 d . . . H1B H 1.636(7) 0.621(3) -0.016(5) 0.037(11) Uiso 1 1 d . . . H1A H 1.840(6) 0.624(2) 0.135(4) 0.015(8) Uiso 1 1 d . . . C4 C 1.4226(4) 0.5244(2) 0.4351(3) 0.0149(5) Uani 1 1 d . . . H4B H 1.337(5) 0.467(3) 0.381(3) 0.020(8) Uiso 1 1 d . . . H4A H 1.307(6) 0.574(3) 0.467(3) 0.019(8) Uiso 1 1 d . . . C2 C 1.5303(5) 0.7130(2) 0.1389(3) 0.0150(5) Uani 1 1 d . . . H2B H 1.414(5) 0.748(2) 0.072(3) 0.008(7) Uiso 1 1 d . . . H2A H 1.579(5) 0.767(2) 0.198(3) 0.011(7) Uiso 1 1 d . . . C3 C 1.4080(5) 0.6297(2) 0.2160(3) 0.0155(6) Uani 1 1 d . . . H3B H 1.354(6) 0.571(3) 0.153(4) 0.026(9) Uiso 1 1 d . . . H3A H 1.279(6) 0.665(3) 0.249(4) 0.023(8) Uiso 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 0.0168(2) 0.0188(2) 0.01437(19) -0.00032(9) 0.00264(12) 0.00360(9) N1 0.0163(11) 0.0168(12) 0.0103(10) 0.0013(9) 0.0024(9) 0.0034(10) N2 0.0128(11) 0.0129(10) 0.0116(10) 0.0023(8) 0.0033(8) 0.0008(9) C1 0.0184(14) 0.0179(14) 0.0170(12) 0.0012(10) 0.0054(11) 0.0009(10) C4 0.0156(13) 0.0143(12) 0.0145(12) 0.0031(10) 0.0022(10) -0.0026(11) C2 0.0174(13) 0.0157(13) 0.0115(12) 0.0025(10) 0.0011(10) 0.0000(10) C3 0.0119(13) 0.0197(14) 0.0142(13) 0.0038(10) 0.0005(10) 0.0001(10) _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 C1 1.501(3) . ? N2 C4 1.485(3) . ? N2 C3 1.488(3) . ? C1 C2 1.521(4) . ? C4 C4 1.525(5) 3_866 ? C2 C3 1.532(4) . ? 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 C4 N2 C3 110.6(2) . . ? N1 C1 C2 110.3(2) . . ? N2 C4 C4 110.6(3) . 3_866 ? C1 C2 C3 113.8(2) . . ? N2 C3 C2 112.1(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 C3 N2 C4 C4 177.4(3) . . . 3_866 ? N1 C1 C2 C3 -173.9(2) . . . . ? C4 N2 C3 C2 167.7(2) . . . . ? C1 C2 C3 N2 69.6(3) . . . . ? 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 H13 Br1 0.93(4) 2.44(4) 3.359(3) 172(3) 2_855 N1 H12 Br1 0.83(3) 2.53(3) 3.339(2) 165(3) 3_865 N1 H11 N2 0.81(4) 2.07(4) 2.875(3) 178(4) 4_575 N2 H21 Br1 0.84(3) 2.71(3) 3.551(2) 171(3) 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.644 _refine_diff_density_min -1.140 _refine_diff_density_rms 0.135 #===END data_5a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H19 Br N4' _chemical_formula_weight 227.16 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 Monoclinic _symmetry_space_group_name_H-M P21/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 8.6143(17) _cell_length_b 8.7903(18) _cell_length_c 13.772(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.50(3) _cell_angle_gamma 90.00 _cell_volume 1038.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 3.915 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8138 _diffrn_reflns_av_R_equivalents 0.097 _diffrn_reflns_av_sigmaI/netI 0.1074 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 30.50 _reflns_number_total 2983 _reflns_number_gt 2636 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0000P)^2^+0.2173P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 2983 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.830073(19) 0.24186(2) 0.134699(12) 0.01561(12) Uani 1 1 d . . . N1 N 1.2956(2) 0.25938(14) 0.05776(13) 0.0136(3) Uani 1 1 d . . . N2 N 1.01151(18) 0.2130(2) -0.07389(12) 0.0154(3) Uani 1 1 d . . . H23 H 1.017(3) 0.210(3) -0.010(2) 0.023(6) Uiso 1 1 d . . . H22 H 0.950(3) 0.142(3) -0.099(2) 0.038(8) Uiso 1 1 d . . . H21 H 0.966(3) 0.305(3) -0.0952(19) 0.028(7) Uiso 1 1 d . . . N3 N 1.17225(18) 0.01513(19) 0.17955(12) 0.0173(3) Uani 1 1 d . . . H32 H 1.117(3) 0.102(3) 0.1691(17) 0.025(6) Uiso 1 1 d . . . H31 H 1.160(3) -0.028(3) 0.2362(18) 0.021(6) Uiso 1 1 d . . . N4 N 1.13348(17) 0.52313(19) 0.14695(12) 0.0173(3) Uani 1 1 d . . . H42 H 1.136(3) 0.536(3) 0.2127(18) 0.020(6) Uiso 1 1 d . . . H41 H 1.088(3) 0.429(3) 0.1320(16) 0.023(6) Uiso 1 1 d . . . C1 C 1.2895(2) 0.2925(2) -0.04784(13) 0.0173(4) Uani 1 1 d . . . H1B H 1.3938 0.2745 -0.0703 0.021 Uiso 1 1 calc R . . H1A H 1.2631 0.4011 -0.0591 0.021 Uiso 1 1 calc R . . C2 C 1.16944(19) 0.1939(2) -0.10753(13) 0.0173(4) Uani 1 1 d . . . H2B H 1.1663 0.2225 -0.1772 0.021 Uiso 1 1 calc R . . H2A H 1.2009 0.0858 -0.1013 0.021 Uiso 1 1 calc R . . C3 C 1.3737(2) 0.1107(2) 0.07934(14) 0.0175(4) Uani 1 1 d . . . H3B H 1.4877 0.1241 0.0790 0.021 Uiso 1 1 calc R . . H3A H 1.3389 0.0377 0.0269 0.021 Uiso 1 1 calc R . . C4 C 1.3399(2) 0.0439(2) 0.17704(13) 0.0195(4) Uani 1 1 d . . . H4B H 1.3980 -0.0526 0.1883 0.023 Uiso 1 1 calc R . . H4A H 1.3761 0.1154 0.2300 0.023 Uiso 1 1 calc R . . C5 C 1.3798(2) 0.3811(2) 0.11517(13) 0.0178(4) Uani 1 1 d . . . H5B H 1.4819 0.3978 0.0895 0.021 Uiso 1 1 calc R . . H5A H 1.4001 0.3471 0.1837 0.021 Uiso 1 1 calc R . . C6 C 1.29091(19) 0.5319(2) 0.11283(13) 0.0175(4) Uani 1 1 d . . . H6B H 1.3534 0.6065 0.1538 0.021 Uiso 1 1 calc R . . H6A H 1.2809 0.5709 0.0451 0.021 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 Br1 0.01325(16) 0.01793(18) 0.01562(17) -0.00026(5) 0.00121(9) 0.00076(5) N1 0.0107(8) 0.0146(8) 0.0152(8) -0.0009(5) -0.0007(6) 0.0003(4) N2 0.0137(7) 0.0180(8) 0.0141(8) -0.0010(7) -0.0008(5) -0.0012(6) N3 0.0168(7) 0.0176(8) 0.0169(8) 0.0041(6) -0.0012(5) -0.0003(6) N4 0.0143(7) 0.0175(8) 0.0201(8) -0.0027(6) 0.0012(6) -0.0011(6) C1 0.0146(8) 0.0200(9) 0.0175(9) 0.0009(8) 0.0027(6) -0.0015(7) C2 0.0150(8) 0.0197(10) 0.0170(8) -0.0007(8) 0.0001(6) -0.0001(6) C3 0.0101(7) 0.0174(9) 0.0250(9) 0.0006(7) 0.0010(6) 0.0028(6) C4 0.0156(8) 0.0205(10) 0.0211(9) 0.0029(7) -0.0048(6) 0.0011(7) C5 0.0112(7) 0.0201(9) 0.0212(9) -0.0041(7) -0.0023(6) 0.0002(6) C6 0.0134(7) 0.0161(9) 0.0228(9) -0.0003(7) 0.0004(6) -0.0023(6) _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 C5 1.479(2) . ? N1 C1 1.479(3) . ? N1 C3 1.487(2) . ? N2 C2 1.488(2) . ? N3 C4 1.470(2) . ? N4 C6 1.479(2) . ? C1 C2 1.527(3) . ? C3 C4 1.522(3) . ? C5 C6 1.530(2) . ? 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 C5 N1 C1 110.64(14) . . ? C5 N1 C3 109.85(15) . . ? C1 N1 C3 109.99(15) . . ? N1 C1 C2 112.06(15) . . ? N2 C2 C1 111.16(15) . . ? N1 C3 C4 113.25(15) . . ? N3 C4 C3 111.04(14) . . ? N1 C5 C6 113.36(14) . . ? N4 C6 C5 114.87(14) . . ? 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 C5 N1 C1 C2 -165.08(15) . . . . ? C3 N1 C1 C2 73.38(19) . . . . ? N1 C1 C2 N2 56.8(2) . . . . ? C5 N1 C3 C4 76.50(19) . . . . ? C1 N1 C3 C4 -161.49(15) . . . . ? N1 C3 C4 N3 61.2(2) . . . . ? C1 N1 C5 C6 69.48(19) . . . . ? C3 N1 C5 C6 -168.90(15) . . . . ? N1 C5 C6 N4 57.1(2) . . . . ? 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 N2 H23 Br1 0.87(3) 2.70(2) 3.4091(18) 139.3(19) . N2 H22 N3 0.87(3) 2.00(3) 2.864(2) 169(2) 3_755 N2 H21 N4 0.94(3) 1.84(3) 2.777(2) 174(3) 3_765 N3 H32 Br1 0.91(3) 2.76(2) 3.5627(17) 148.4(19) . N3 H31 Br1 0.88(2) 2.69(2) 3.5107(17) 155.4(19) 2_745 N4 H42 Br1 0.91(2) 2.77(2) 3.5577(18) 145.6(19) 2_755 N4 H41 Br1 0.93(3) 2.76(2) 3.5900(16) 148.0(18) . _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 1.517 _refine_diff_density_min -1.886 _refine_diff_density_rms 0.331 #===END data_5b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H21 I N4 O' _chemical_formula_weight 292.17 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' 'I' 'I' -0.4742 1.8119 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5019(17) _cell_length_b 9.6112(19) _cell_length_c 14.840(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.08(3) _cell_angle_gamma 90.00 _cell_volume 1212.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.7 _exptl_crystal_size_min 0.7 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 2.614 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16396 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2367 _reflns_number_gt 2199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0000P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0067(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 2367 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0636 _refine_ls_wR_factor_gt 0.0607 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.002 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 I1 I 0.249396(15) 0.654527(14) 0.075734(8) 0.01766(11) Uani 1 1 d . . . O1 O 0.2300(2) 1.51444(18) -0.21393(10) 0.0180(3) Uani 1 1 d . . . H102 H 0.163(4) 1.562(4) -0.213(2) 0.039(10) Uiso 1 1 d . . . H101 H 0.317(3) 1.573(4) -0.1980(18) 0.032(7) Uiso 1 1 d . . . N1 N 0.24812(19) 1.15500(18) 0.07906(11) 0.0140(5) Uani 1 1 d . . . N2 N 0.1753(3) 1.35032(19) -0.07155(14) 0.0173(5) Uani 1 1 d . . . H23 H 0.084(5) 1.338(3) -0.065(3) 0.047(12) Uiso 1 1 d . . . H22 H 0.212(3) 1.377(3) -0.0211(19) 0.010(6) Uiso 1 1 d . . . H21 H 0.212(4) 1.399(5) -0.121(2) 0.047(9) Uiso 1 1 d . . . N3 N 0.0447(3) 1.3264(2) 0.20982(15) 0.0206(5) Uani 1 1 d . . . H32 H 0.104(4) 1.367(3) 0.169(2) 0.027(8) Uiso 1 1 d . . . H31 H 0.099(4) 1.311(3) 0.265(2) 0.034(8) Uiso 1 1 d . . . N4 N 0.5167(3) 1.3462(2) 0.14151(16) 0.0223(5) Uani 1 1 d . . . H42 H 0.430(5) 1.388(4) 0.140(2) 0.045(9) Uiso 1 1 d . . . H41 H 0.544(4) 1.363(3) 0.082(2) 0.031(8) Uiso 1 1 d . . . C1 C 0.1870(3) 1.1104(3) -0.00982(13) 0.0178(4) Uani 1 1 d . . . H1B H 0.067(3) 1.105(4) -0.0112(18) 0.028(7) Uiso 1 1 d . . . H1A H 0.217(3) 1.011(3) -0.0262(16) 0.016(6) Uiso 1 1 d . . . C2 C 0.2389(3) 1.2077(3) -0.08545(13) 0.0182(5) Uani 1 1 d . . . H2B H 0.355(3) 1.229(3) -0.0898(17) 0.024(6) Uiso 1 1 d . . . H2A H 0.202(3) 1.173(2) -0.1439(18) 0.011(6) Uiso 1 1 d . . . C3 C 0.1495(3) 1.0972(2) 0.15139(14) 0.0170(4) Uani 1 1 d . . . H3B H 0.204(3) 1.090(3) 0.2091(17) 0.019(6) Uiso 1 1 d . . . H3A H 0.111(3) 0.998(3) 0.1404(14) 0.012(5) Uiso 1 1 d . . . C4 C 0.0059(3) 1.1890(3) 0.16938(16) 0.0196(5) Uani 1 1 d . . . H4B H -0.061(3) 1.138(3) 0.2089(19) 0.018(7) Uiso 1 1 d . . . H4A H -0.056(3) 1.194(3) 0.114(2) 0.022(7) Uiso 1 1 d . . . C5 C 0.4145(3) 1.1121(3) 0.09235(14) 0.0193(4) Uani 1 1 d . . . H5B H 0.407(3) 1.012(3) 0.1077(18) 0.030(7) Uiso 1 1 d . . . H5A H 0.466(3) 1.132(3) 0.0350(17) 0.013(6) Uiso 1 1 d . . . C6 C 0.5019(3) 1.1983(3) 0.16399(16) 0.0225(5) Uani 1 1 d . . . H6B H 0.623(4) 1.170(3) 0.174(2) 0.039(9) Uiso 1 1 d . . . H6A H 0.453(3) 1.202(3) 0.2226(18) 0.022(6) Uiso 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 I1 0.01890(14) 0.01803(16) 0.01600(14) -0.00080(4) -0.00085(8) -0.00048(5) O1 0.0183(8) 0.0162(9) 0.0196(7) -0.0008(6) -0.0007(6) 0.0000(7) N1 0.0175(12) 0.0143(15) 0.0102(11) 0.0008(5) -0.0012(10) -0.0011(6) N2 0.0185(12) 0.0183(12) 0.0150(11) -0.0004(7) -0.0004(9) -0.0010(7) N3 0.0205(10) 0.0217(11) 0.0196(10) 0.0015(8) 0.0020(9) 0.0021(8) N4 0.0158(10) 0.0237(14) 0.0272(12) -0.0008(7) -0.0029(9) -0.0009(8) C1 0.0255(12) 0.0122(11) 0.0157(10) -0.0008(8) -0.0005(8) -0.0029(9) C2 0.0254(11) 0.0152(14) 0.0142(10) 0.0002(8) 0.0022(9) 0.0000(9) C3 0.0205(10) 0.0136(13) 0.0170(10) 0.0035(8) 0.0014(8) -0.0019(9) C4 0.0165(11) 0.0229(13) 0.0196(11) 0.0017(10) 0.0026(9) -0.0010(10) C5 0.0177(10) 0.0198(13) 0.0204(10) -0.0010(9) 0.0007(9) 0.0033(9) C6 0.0175(11) 0.0266(14) 0.0232(11) 0.0015(10) -0.0032(9) -0.0013(10) _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 C1 1.472(3) . ? N1 C3 1.482(3) . ? N1 C5 1.483(3) . ? N2 C2 1.489(3) . ? N3 C4 1.485(3) . ? N4 C6 1.465(3) . ? C1 C2 1.532(3) . ? C3 C4 1.534(3) . ? C5 C6 1.529(3) . ? 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 C1 N1 C3 110.16(17) . . ? C1 N1 C5 110.95(16) . . ? C3 N1 C5 110.53(17) . . ? N1 C1 C2 112.13(19) . . ? N2 C2 C1 110.51(17) . . ? N1 C3 C4 111.91(18) . . ? N3 C4 C3 114.24(19) . . ? N1 C5 C6 113.04(19) . . ? N4 C6 C5 114.2(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 C3 N1 C1 C2 157.58(18) . . . . ? C5 N1 C1 C2 -79.7(2) . . . . ? N1 C1 C2 N2 -62.4(2) . . . . ? C1 N1 C3 C4 -85.2(2) . . . . ? C5 N1 C3 C4 151.87(19) . . . . ? N1 C3 C4 N3 -67.9(2) . . . . ? C1 N1 C5 C6 158.43(19) . . . . ? C3 N1 C5 C6 -79.1(2) . . . . ? N1 C5 C6 N4 -63.5(3) . . . . ? 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 O1 H102 N3 0.73(4) 2.07(4) 2.793(3) 172(4) 3_585 O1 H101 N4 0.95(3) 1.81(3) 2.739(3) 164(3) 3_685 N2 H23 I1 0.79(4) 2.84(4) 3.611(2) 165(3) 3_575 N2 H22 I1 0.85(3) 3.04(3) 3.697(2) 136(2) 1_565 N2 H21 O1 0.93(4) 1.77(4) 2.684(3) 164(3) . N3 H31 I1 0.94(4) 3.07(4) 3.964(3) 160(3) 2 N4 H42 I1 0.84(4) 3.13(4) 3.849(2) 146(3) 1_565 N4 H41 I1 0.93(3) 2.96(3) 3.820(3) 155(2) 3_675 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.773 _refine_diff_density_min -1.046 _refine_diff_density_rms 0.166 #===END data_5c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H21 Cl3 N4' _chemical_formula_weight 255.62 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Cubic _symmetry_space_group_name_H-M P2(1)3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 'z, x, y' 'z+1/2, -x+1/2, -y' '-z+1/2, -x, y+1/2' '-z, x+1/2, -y+1/2' 'y, z, x' '-y, z+1/2, -x+1/2' 'y+1/2, -z+1/2, -x' '-y+1/2, -z, x+1/2' _cell_length_a 10.8750(13) _cell_length_b 10.8750(13) _cell_length_c 10.8750(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1286.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.6 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.683 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2576 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.92 _reflns_number_total 747 _reflns_number_gt 725 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0122P)^2^+0.3842P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0143(19) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(9) _refine_ls_number_reflns 747 _refine_ls_number_parameters 69 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0208 _refine_ls_R_factor_gt 0.0199 _refine_ls_wR_factor_ref 0.0477 _refine_ls_wR_factor_gt 0.0473 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 Cl1 Cl 0.68251(4) 0.81749(4) 0.18251(4) 0.02181(19) Uani 1 3 d S . . Cl2 Cl 0.05054(3) 0.05054(3) 0.05054(3) 0.01574(18) Uani 1 3 d S . . Cl3 Cl -0.31191(4) 0.18809(4) 0.31191(4) 0.01883(18) Uani 1 3 d S . . N1 N -0.24152(14) 0.03473(16) 0.00270(16) 0.0206(4) Uani 1 1 d . . . H13 H -0.269(2) -0.012(2) 0.060(2) 0.034(6) Uiso 1 1 d . . . H12 H -0.228(3) -0.026(3) -0.065(3) 0.056(8) Uiso 1 1 d . . . H11 H -0.167(2) 0.055(2) 0.0287(19) 0.029(6) Uiso 1 1 d . . . N2 N -0.51647(12) 0.01647(12) -0.01647(12) 0.0116(5) Uani 1 3 d S . . C1 C -0.32321(16) 0.14005(15) -0.02877(15) 0.0164(4) Uani 1 1 d . . . H1B H -0.2798(17) 0.1940(19) -0.0860(19) 0.021(5) Uiso 1 1 d . . . H1A H -0.3409(16) 0.1770(15) 0.0528(18) 0.013(4) Uiso 1 1 d . . . C2 C -0.43772(17) 0.09612(16) -0.09419(15) 0.0168(4) Uani 1 1 d . . . H2B H -0.4868(19) 0.172(2) -0.1246(18) 0.033(6) Uiso 1 1 d . . . H2A H -0.4081(18) 0.0470(19) -0.172(2) 0.028(5) Uiso 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 Cl1 0.02181(19) 0.02181(19) 0.02181(19) 0.00427(17) -0.00427(17) 0.00427(17) Cl2 0.01574(18) 0.01574(18) 0.01574(18) -0.00183(16) -0.00183(16) -0.00183(16) Cl3 0.01883(18) 0.01883(18) 0.01883(18) 0.00060(17) 0.00060(17) -0.00060(17) N1 0.0132(8) 0.0200(8) 0.0287(9) 0.0003(7) 0.0002(7) -0.0025(6) N2 0.0116(5) 0.0116(5) 0.0116(5) -0.0025(5) 0.0025(5) -0.0025(5) C1 0.0188(8) 0.0147(7) 0.0156(8) 0.0008(6) 0.0023(7) -0.0050(7) C2 0.0180(9) 0.0172(8) 0.0151(8) 0.0037(7) 0.0019(7) -0.0011(7) _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 C1 1.489(2) . ? N2 C2 1.4826(19) 6_445 ? N2 C2 1.4826(19) 12_455 ? N2 C2 1.4826(19) . ? C1 C2 1.512(2) . ? 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 C2 N2 C2 109.50(11) 6_445 12_455 ? C2 N2 C2 109.50(11) 6_445 . ? C2 N2 C2 109.50(11) 12_455 . ? N1 C1 C2 110.89(14) . . ? N2 C2 C1 113.09(15) . . ? 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 C2 N2 C2 C1 -156.67(15) 6_445 . . . ? C2 N2 C2 C1 83.3(2) 12_455 . . . ? N1 C1 C2 N2 64.09(18) . . . . ? 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 H13 Cl1 0.86(3) 2.34(3) 3.1761(18) 164(2) 1_445 N1 H12 Cl3 1.00(3) 2.25(3) 3.2426(18) 169(2) 2_454 N1 H11 Cl2 0.88(2) 2.38(2) 3.2231(16) 159(2) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.92 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.192 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.035 #===END data_5d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H21 I3 N4' _chemical_formula_weight 529.97 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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Hexagonal _symmetry_space_group_name_H-M R3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x+y, y, z+1/2' 'x, x-y, z+1/2' '-y, -x, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' '-y+2/3, -x+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' '-y+1/3, -x+2/3, z+7/6' _cell_length_a 16.501(2) _cell_length_b 16.501(2) _cell_length_c 9.5919(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2261.8(6) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 6.194 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9839 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_sigmaI/netI 0.0712 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.28 _diffrn_reflns_theta_max 27.49 _reflns_number_total 947 _reflns_number_gt 945 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0417P)^2^+5.8636P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00164(19) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.56(8) _refine_ls_number_reflns 947 _refine_ls_number_parameters 41 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 I1 I 0.89969(3) 0.21282(3) 0.3292 0.0076(2) Uani 1 1 d . . . N1 N 0.7646(4) -0.0180(4) 0.1770(6) 0.0076(11) Uani 1 1 d . . . H13 H 0.7849 0.0440 0.1647 0.009 Uiso 1 1 calc R . . H12 H 0.7205 -0.0411 0.2455 0.009 Uiso 1 1 calc R . . H11 H 0.7393 -0.0493 0.0961 0.009 Uiso 1 1 calc R . . N2 N 1.0000 0.0000 0.1492(12) 0.008(2) Uani 1 3 d S . . C1 C 0.8444(5) -0.0302(5) 0.2174(7) 0.0065(13) Uani 1 1 d . . . H1B H 0.8232 -0.0977 0.2259 0.008 Uiso 1 1 calc R . . H1A H 0.8690 -0.0004 0.3091 0.008 Uiso 1 1 calc R . . C2 C 0.9225(5) 0.0148(5) 0.1061(8) 0.0089(14) Uani 1 1 d . . . H2B H 0.8981 -0.0144 0.0141 0.011 Uiso 1 1 calc R . . H2A H 0.9449 0.0826 0.0986 0.011 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 I1 0.0065(3) 0.0054(3) 0.0085(3) -0.00010(15) -0.00004(14) 0.00118(17) N1 0.004(3) 0.010(3) 0.009(3) -0.002(2) 0.000(2) 0.003(2) N2 0.003(3) 0.003(3) 0.018(5) 0.000 0.000 0.0015(14) C1 0.004(3) 0.008(3) 0.010(3) 0.002(3) 0.001(3) 0.005(3) C2 0.009(4) 0.012(3) 0.009(3) 0.001(3) 0.002(3) 0.008(3) _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 C1 1.480(9) . ? N2 C2 1.476(8) 2_645 ? N2 C2 1.476(8) 3_765 ? N2 C2 1.476(8) . ? C1 C2 1.548(10) . ? 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 C2 N2 C2 112.5(4) 2_645 3_765 ? C2 N2 C2 112.5(4) 2_645 . ? C2 N2 C2 112.5(4) 3_765 . ? N1 C1 C2 109.8(5) . . ? N2 C2 C1 108.1(6) . . ? 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 C2 N2 C2 C1 84.1(10) 2_645 . . . ? C2 N2 C2 C1 -147.6(7) 3_765 . . . ? N1 C1 C2 N2 -179.2(5) . . . . ? 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 H13 I1 0.91 2.93 3.621(6) 134.3 . N1 H12 I1 0.91 2.72 3.566(6) 155.9 16_644 N1 H11 I1 0.91 2.80 3.535(6) 139.1 15_654 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.648 _refine_diff_density_min -1.302 _refine_diff_density_rms 0.289 #===END data_5e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H46 Br8 N8 O2' _chemical_formula_weight 973.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(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 14.889(3) _cell_length_b 10.685(2) _cell_length_c 20.754(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.92(3) _cell_angle_gamma 90.00 _cell_volume 3175.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.037 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1880 _exptl_absorpt_coefficient_mu 10.127 _exptl_absorpt_correction_type scalepack _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KAPPACCD _diffrn_measurement_method '2o phi frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 27438 _diffrn_reflns_av_R_equivalents 0.095 _diffrn_reflns_av_sigmaI/netI 0.1418 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6191 _reflns_number_gt 4822 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZOSMN _computing_data_reduction DENZOSMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics RES2INS _computing_publication_material ? _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^)+(0.0000P)^2^+11.6886P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00035(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^' _refine_ls_number_reflns 6191 _refine_ls_number_parameters 288 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0808 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1288 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.729 _refine_ls_shift/su_mean 0.005 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 0.00793(5) 0.11385(7) 0.19054(4) 0.0112(2) Uani 1 1 d . . . Br2 Br 0.45272(5) 0.39252(7) 0.19717(4) 0.0157(2) Uani 1 1 d . . . Br3 Br 0.26785(5) 0.22583(8) 0.31263(4) 0.0165(2) Uani 1 1 d . . . Br4 Br 0.35031(5) -0.43605(7) -0.03076(4) 0.0146(2) Uani 1 1 d . . . Br5 Br 0.10675(5) -0.14262(8) 0.04112(4) 0.0164(2) Uani 1 1 d . . . Br6 Br 0.31077(5) 0.51361(7) 0.45275(4) 0.0147(2) Uani 1 1 d . . . Br7 Br 0.22015(6) 0.76289(7) 0.25699(4) 0.0165(2) Uani 1 1 d . . . Br8 Br 0.18483(7) 0.26438(9) 0.06603(4) 0.0314(3) Uani 1 1 d . . . O1 O 0.4214(5) 0.2670(7) 0.0077(4) 0.0222(15) Uani 1 1 d . . . H102 H 0.387(6) 0.205(9) -0.002(4) 0.01(2) Uiso 1 1 d . . . H101 H 0.385(8) 0.313(11) 0.014(6) 0.04(4) Uiso 1 1 d . . . O2 O 0.2526(4) 0.6216(6) 0.0986(3) 0.0267(16) Uani 1 1 d . . . N1 N -0.0924(5) 0.8915(6) 0.0798(4) 0.0217(19) Uani 1 1 d . . . H13 H -0.1534 0.9079 0.0768 0.026 Uiso 1 1 calc R . . H12 H -0.0873 0.8639 0.0395 0.026 Uiso 1 1 calc R . . H11 H -0.0581 0.9626 0.0915 0.026 Uiso 1 1 calc R . . N2 N -0.0305(4) 0.5647(6) 0.1533(4) 0.0137(16) Uani 1 1 d . . . H21 H -0.017(5) 0.590(7) 0.191(4) 0.00(2) Uiso 1 1 d . . . N3 N -0.1611(4) 0.2670(6) 0.0853(3) 0.0095(14) Uani 1 1 d . . . H33 H -0.2203 0.2975 0.0767 0.011 Uiso 1 1 calc R . . H32 H -0.1457 0.2277 0.1258 0.011 Uiso 1 1 calc R . . H31 H -0.1578 0.2115 0.0528 0.011 Uiso 1 1 calc R . . N4 N 0.2217(4) 0.4502(6) 0.1954(4) 0.0193(17) Uani 1 1 d . . . H43 H 0.2440 0.5291 0.1938 0.023 Uiso 1 1 calc R . . H42 H 0.2228 0.4081 0.1575 0.023 Uiso 1 1 calc R . . H41 H 0.2580 0.4094 0.2317 0.023 Uiso 1 1 calc R . . N5 N 0.5907(5) 0.2153(6) 0.1236(4) 0.0186(16) Uani 1 1 d . . . H53 H 0.5399 0.2635 0.1047 0.022 Uiso 1 1 calc R . . H52 H 0.6148 0.1848 0.0909 0.022 Uiso 1 1 calc R . . H51 H 0.6346 0.2624 0.1527 0.022 Uiso 1 1 calc R . . N6 N 0.4428(4) -0.0604(6) 0.1438(3) 0.0111(14) Uani 1 1 d . . . H61 H 0.470(5) -0.055(7) 0.184(4) 0.000(19) Uiso 1 1 d . . . N7 N 0.2162(4) 0.0370(6) 0.1791(4) 0.0184(17) Uani 1 1 d . . . H73 H 0.1919 -0.0397 0.1834 0.022 Uiso 1 1 calc R . . H72 H 0.1894 0.0674 0.1372 0.022 Uiso 1 1 calc R . . H71 H 0.2045 0.0901 0.2101 0.022 Uiso 1 1 calc R . . N8 N 0.5210(5) -0.3855(6) 0.1110(3) 0.0170(16) Uani 1 1 d . . . H83 H 0.5811 -0.3630 0.1144 0.020 Uiso 1 1 calc R . . H82 H 0.4887 -0.3912 0.0669 0.020 Uiso 1 1 calc R . . H81 H 0.5203 -0.4610 0.1311 0.020 Uiso 1 1 calc R . . C1 C -0.0569(6) 0.7931(7) 0.1318(4) 0.0167(19) Uani 1 1 d . . . H1B H -0.0854 0.8049 0.1692 0.020 Uiso 1 1 calc R . . H1A H 0.0116 0.8015 0.1499 0.020 Uiso 1 1 calc R . . C2 C -0.0803(5) 0.6627(7) 0.1020(4) 0.0107(16) Uani 1 1 d U . . H2B H -0.0600 0.6548 0.0606 0.013 Uiso 1 1 calc R . . H2A H -0.1487 0.6491 0.0904 0.013 Uiso 1 1 calc R . . C3 C -0.0872(5) 0.4494(7) 0.1508(4) 0.0137(18) Uani 1 1 d . . . H3B H -0.1506 0.4729 0.1529 0.016 Uiso 1 1 calc R . . H3A H -0.0584 0.3970 0.1904 0.016 Uiso 1 1 calc R . . C4 C -0.0947(5) 0.3726(7) 0.0866(4) 0.0104(17) Uani 1 1 d . . . H4B H -0.1179 0.4261 0.0465 0.013 Uiso 1 1 calc R . . H4A H -0.0326 0.3395 0.0866 0.013 Uiso 1 1 calc R . . C5 C 0.0662(5) 0.5428(7) 0.1452(4) 0.0149(19) Uani 1 1 d . . . H5B H 0.0988 0.6241 0.1470 0.018 Uiso 1 1 calc R . . H5A H 0.0610 0.5046 0.1009 0.018 Uiso 1 1 calc R . . C6 C 0.1234(5) 0.4566(7) 0.2004(4) 0.0123(17) Uani 1 1 d . . . H6B H 0.1229 0.4895 0.2449 0.015 Uiso 1 1 calc R . . H6A H 0.0955 0.3718 0.1954 0.015 Uiso 1 1 calc R . . C7 C 0.5623(6) 0.1085(7) 0.1606(4) 0.0163(19) Uani 1 1 d . . . H7B H 0.5566 0.1369 0.2047 0.020 Uiso 1 1 calc R . . H7A H 0.6093 0.0407 0.1679 0.020 Uiso 1 1 calc R . . C8 C 0.4689(5) 0.0621(7) 0.1176(4) 0.0096(16) Uani 1 1 d U . . H8B H 0.4202 0.1253 0.1173 0.012 Uiso 1 1 calc R . . H8A H 0.4722 0.0508 0.0710 0.012 Uiso 1 1 calc R . . C9 C 0.3393(5) -0.0620(7) 0.1391(4) 0.0143(18) Uani 1 1 d . . . H9B H 0.3030 -0.0363 0.0935 0.017 Uiso 1 1 calc R . . H9A H 0.3199 -0.1478 0.1472 0.017 Uiso 1 1 calc R . . C10 C 0.3194(5) 0.0258(8) 0.1898(4) 0.0162(18) Uani 1 1 d . . . H10B H 0.3489 -0.0060 0.2355 0.019 Uiso 1 1 calc R . . H10A H 0.3461 0.1091 0.1854 0.019 Uiso 1 1 calc R . . C11 C 0.4765(6) -0.1659(7) 0.1086(4) 0.0157(18) Uani 1 1 d . . . H11B H 0.5405 -0.1471 0.1060 0.019 Uiso 1 1 calc R . . H11A H 0.4356 -0.1726 0.0622 0.019 Uiso 1 1 calc R . . C12 C 0.4768(6) -0.2902(7) 0.1442(4) 0.0133(18) Uani 1 1 d . . . H12B H 0.5123 -0.2822 0.1919 0.016 Uiso 1 1 calc R . . H12A H 0.4121 -0.3154 0.1420 0.016 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 Br1 0.0089(4) 0.0153(4) 0.0077(3) 0.0001(3) -0.0008(3) 0.0015(3) Br2 0.0144(4) 0.0173(4) 0.0136(4) 0.0003(3) 0.0006(3) 0.0000(3) Br3 0.0134(4) 0.0196(4) 0.0139(4) 0.0004(3) -0.0007(3) 0.0026(3) Br4 0.0122(4) 0.0149(4) 0.0151(4) 0.0015(3) 0.0011(3) 0.0017(3) Br5 0.0128(4) 0.0210(4) 0.0148(4) -0.0026(3) 0.0030(3) -0.0001(3) Br6 0.0127(4) 0.0161(4) 0.0140(4) 0.0010(3) 0.0014(3) -0.0010(3) Br7 0.0193(4) 0.0157(4) 0.0133(4) 0.0003(3) 0.0026(3) -0.0026(3) Br8 0.0486(6) 0.0267(5) 0.0124(4) -0.0001(4) -0.0023(4) -0.0073(4) O1 0.021(3) 0.016(3) 0.030(4) 0.003(3) 0.008(3) 0.000(3) O2 0.027(3) 0.025(3) 0.027(3) 0.001(3) 0.006(3) 0.003(3) N1 0.026(4) 0.007(3) 0.025(4) 0.002(3) -0.007(3) 0.000(3) N2 0.010(3) 0.018(4) 0.010(3) -0.004(3) -0.003(3) -0.005(3) N3 0.007(3) 0.011(3) 0.008(3) 0.003(3) -0.002(3) -0.002(2) N4 0.012(3) 0.018(4) 0.022(4) 0.004(3) -0.005(3) 0.001(3) N5 0.013(3) 0.019(4) 0.025(4) 0.006(3) 0.008(3) 0.004(3) N6 0.009(3) 0.013(3) 0.011(3) 0.002(3) 0.002(3) 0.002(3) N7 0.007(3) 0.021(4) 0.024(4) 0.003(3) -0.001(3) 0.002(3) N8 0.015(3) 0.020(4) 0.013(3) -0.008(3) -0.001(3) 0.005(3) C1 0.022(4) 0.010(4) 0.015(4) 0.001(3) 0.000(4) 0.000(3) C2 0.009(3) 0.013(3) 0.007(3) -0.002(3) -0.004(3) -0.001(3) C3 0.009(4) 0.018(4) 0.013(4) -0.005(3) 0.003(3) -0.004(3) C4 0.008(4) 0.010(4) 0.011(4) 0.000(3) -0.001(3) 0.001(3) C5 0.007(4) 0.019(4) 0.017(4) -0.002(4) -0.001(3) -0.001(3) C6 0.010(4) 0.014(4) 0.013(4) 0.001(3) 0.003(3) -0.004(3) C7 0.018(4) 0.014(4) 0.015(4) 0.002(3) 0.001(3) 0.003(3) C8 0.009(3) 0.011(3) 0.012(3) 0.001(3) 0.009(3) 0.002(3) C9 0.011(4) 0.017(4) 0.014(4) 0.000(3) 0.002(3) 0.005(3) C10 0.012(4) 0.020(4) 0.013(4) 0.005(4) -0.002(3) -0.002(3) C11 0.014(4) 0.011(4) 0.019(4) 0.001(4) 0.001(3) 0.006(3) C12 0.020(4) 0.014(4) 0.007(3) -0.003(3) 0.006(3) 0.006(3) _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 C1 1.495(10) . ? N2 C3 1.486(10) . ? N2 C5 1.512(11) . ? N2 C2 1.532(9) . ? N3 C4 1.496(9) . ? N4 C6 1.497(10) . ? N5 C7 1.500(11) . ? N6 C11 1.503(10) . ? N6 C8 1.509(10) . ? N6 C9 1.517(10) . ? N7 C10 1.496(10) . ? N8 C12 1.481(10) . ? C1 C2 1.525(10) . ? C3 C4 1.543(11) . ? C5 C6 1.533(10) . ? C7 C8 1.514(10) . ? C9 C10 1.498(12) . ? C11 C12 1.519(11) . ? 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 C3 N2 C5 114.7(6) . . ? C3 N2 C2 112.4(5) . . ? C5 N2 C2 108.9(7) . . ? C11 N6 C8 108.8(6) . . ? C11 N6 C9 115.4(6) . . ? C8 N6 C9 110.1(6) . . ? N1 C1 C2 110.8(6) . . ? C1 C2 N2 109.3(5) . . ? N2 C3 C4 112.1(7) . . ? N3 C4 C3 107.9(7) . . ? N2 C5 C6 111.1(7) . . ? N4 C6 C5 109.2(7) . . ? N5 C7 C8 106.9(6) . . ? N6 C8 C7 111.0(6) . . ? C10 C9 N6 109.9(6) . . ? N7 C10 C9 109.8(6) . . ? N6 C11 C12 112.1(7) . . ? N8 C12 C11 108.5(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 N1 C1 C2 N2 171.5(7) . . . . ? C3 N2 C2 C1 144.4(7) . . . . ? C5 N2 C2 C1 -87.4(8) . . . . ? C5 N2 C3 C4 -54.5(8) . . . . ? C2 N2 C3 C4 70.5(8) . . . . ? N2 C3 C4 N3 -173.9(5) . . . . ? C3 N2 C5 C6 -59.6(8) . . . . ? C2 N2 C5 C6 173.6(6) . . . . ? N2 C5 C6 N4 -173.2(6) . . . . ? C11 N6 C8 C7 -92.7(7) . . . . ? C9 N6 C8 C7 139.9(7) . . . . ? N5 C7 C8 N6 169.2(6) . . . . ? C11 N6 C9 C10 165.4(6) . . . . ? C8 N6 C9 C10 -71.0(8) . . . . ? N6 C9 C10 N7 172.6(6) . . . . ? C8 N6 C11 C12 164.6(6) . . . . ? C9 N6 C11 C12 -71.1(8) . . . . ? N6 C11 C12 N8 -173.5(6) . . . . ? 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 O1 H102 Br6 0.82(9) 2.66(10) 3.460(7) 165(9) 4_565 O1 H101 Br4 0.76(12) 2.83(12) 3.371(7) 130(12) 1_565 N1 H13 Br6 0.91 2.52 3.395(7) 161.2 2 N1 H12 Br8 0.91 2.65 3.398(7) 139.6 3_565 N1 H11 Br1 0.91 2.59 3.358(7) 142.7 1_565 N2 H21 Br1 0.79(8) 2.45(9) 3.209(7) 162(8) 2 N3 H33 Br4 0.91 2.42 3.276(6) 157.7 3 N3 H32 Br1 0.91 2.61 3.281(6) 130.8 . N3 H32 Br7 0.91 2.96 3.614(7) 130.0 2_545 N3 H31 Br5 0.91 2.39 3.237(7) 154.0 3 N4 H43 O2 0.91 2.25 2.848(10) 123.3 . N4 H43 Br7 0.91 2.89 3.580(7) 133.9 . N4 H42 Br8 0.91 2.39 3.262(7) 161.6 . N4 H41 Br3 0.91 2.56 3.350(7) 145.6 . N5 H53 O1 0.91 2.28 3.019(9) 137.6 . N5 H53 Br2 0.91 2.94 3.444(8) 116.6 . N5 H52 Br6 0.91 2.44 3.253(8) 149.1 2_645 N5 H51 Br7 0.91 2.44 3.241(6) 146.5 2_645 N6 H61 Br2 0.82(7) 2.49(8) 3.279(7) 163(7) 2_645 N7 H73 Br7 0.91 2.57 3.338(7) 142.4 1_545 N7 H72 Br8 0.91 2.56 3.320(7) 141.1 . N7 H72 Br5 0.91 3.03 3.460(7) 110.9 . N7 H71 Br3 0.91 2.53 3.343(7) 148.4 . N7 H71 Br1 0.91 2.85 3.279(7) 110.1 . N8 H83 Br3 0.91 2.53 3.329(6) 147.2 2_645 N8 H82 Br4 0.91 2.51 3.362(6) 156.1 . N8 H81 Br2 0.91 2.47 3.295(8) 151.0 1_545 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.535 _refine_diff_density_min -1.082 _refine_diff_density_rms 0.237 #===END