data_dr2090 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H26 Br N3 O' _chemical_formula_weight 284.25 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 Tetragonal _symmetry_space_group_name_H-M P4(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+1/4' 'y+1/2, -x+1/2, z+3/4' '-x+1/2, y+1/2, -z+1/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 9.6903(12) _cell_length_b 9.6903(12) _cell_length_c 34.257(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3216.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 54 _cell_measurement_theta_min 1.47 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 2.542 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.906360 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS, Bruker (2000)' _exptl_special_details ; Data collection is performed with three batch runs at phi = 0.00 deg (606 frames), at phi = 90.00 deg (435 frames), and at phi = 180 deg (230 frames) A fourth batch run is collected at phi = 0.00 deg (50 frames) to monitor crystal and diffractometer stability. Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data. ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 9398 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.1007 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 28.96 _reflns_number_total 3636 _reflns_number_gt 1871 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker (2000)' _computing_cell_refinement 'SMART, Bruker (2000)' _computing_data_reduction 'XPREP, Bruker (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker (2000)' _computing_publication_material 'SHELXTL, Bruker (2000)' _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^)+(0.0300P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(2) _refine_ls_number_reflns 3636 _refine_ls_number_parameters 171 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1457 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0764 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Br Br 0.08824(5) 0.78597(6) 0.049930(15) 0.0727(2) Uani 1 1 d . . . O1 O -0.3112(4) 0.4944(5) 0.20744(10) 0.1045(16) Uani 1 1 d D . . H1 H -0.372(5) 0.438(6) 0.2026(14) 0.125 Uiso 1 1 d D . . H2 H -0.300(5) 0.511(5) 0.2314(11) 0.125 Uiso 1 1 d D . . N1 N -0.0305(8) 0.6100(8) 0.1360(3) 0.055(2) Uani 0.56 1 d P A 1 H1A H 0.0027 0.6133 0.1125 0.066 Uiso 0.56 1 calc PR A 1 N2 N 0.1822(8) 0.5263(8) 0.1559(2) 0.056(2) Uani 0.56 1 d P A 1 H2A H 0.2177 0.4656 0.1717 0.068 Uiso 0.56 1 calc PR A 1 N3 N -0.0134(9) 0.4628(7) 0.1892(2) 0.056(2) Uani 0.56 1 d P A 1 H3A H -0.0983 0.4385 0.1847 0.067 Uiso 0.56 1 calc PR A 1 N1' N -0.0677(11) 0.6022(11) 0.1620(3) 0.056(3) Uani 0.44 1 d P A 2 H1'B H -0.1044 0.5925 0.1850 0.067 Uiso 0.44 1 calc PR A 2 N2' N 0.1485(10) 0.5741(11) 0.1323(3) 0.064(3) Uani 0.44 1 d P A 2 H2'D H 0.1103 0.5931 0.1099 0.077 Uiso 0.44 1 calc PR A 2 N3' N 0.1014(10) 0.4680(10) 0.1921(3) 0.069(3) Uani 0.44 1 d P A 2 H3'D H 0.1890 0.4493 0.1901 0.082 Uiso 0.44 1 calc PR A 2 C1 C -0.1514(7) 0.6762(8) 0.1394(2) 0.139(3) Uani 1 1 d . . . H1C H -0.2016 0.6009 0.1528 0.167 Uiso 0.56 1 calc PR A 1 H1A H -0.0743 0.7221 0.1275 0.167 Uiso 0.44 1 d PR A 2 C2 C -0.1863(8) 0.7834(8) 0.1665(3) 0.207(5) Uani 1 1 d . A . H2A H -0.2448 0.8509 0.1537 0.310 Uiso 1 1 calc R . . H2B H -0.1026 0.8280 0.1756 0.310 Uiso 1 1 calc R . . H2C H -0.2351 0.7439 0.1886 0.310 Uiso 1 1 calc R . . C3 C -0.2235(6) 0.6677(8) 0.1035(2) 0.172(4) Uani 1 1 d . A . H3A H -0.2708 0.7541 0.0986 0.258 Uiso 1 1 calc R . . H3B H -0.2904 0.5933 0.1048 0.258 Uiso 1 1 calc R . . H3C H -0.1586 0.6497 0.0826 0.258 Uiso 1 1 calc R . . C4 C 0.2836(7) 0.5851(8) 0.13129(17) 0.120(2) Uani 1 1 d . . . H4B H 0.2265 0.6599 0.1200 0.144 Uiso 0.56 1 calc PR A 1 H4A H 0.2986 0.5028 0.1463 0.144 Uiso 0.44 1 d PR A 2 C5 C 0.3786(6) 0.6704(7) 0.1532(2) 0.152(3) Uani 1 1 d . A . H5A H 0.3329 0.7052 0.1764 0.228 Uiso 1 1 calc R . . H5B H 0.4083 0.7473 0.1372 0.228 Uiso 1 1 calc R . . H5C H 0.4582 0.6159 0.1608 0.228 Uiso 1 1 calc R . . C6 C 0.3338(7) 0.5258(7) 0.0946(2) 0.142(3) Uani 1 1 d . A . H6A H 0.2602 0.4739 0.0822 0.213 Uiso 1 1 calc R . . H6B H 0.4110 0.4649 0.0999 0.213 Uiso 1 1 calc R . . H6C H 0.3635 0.5994 0.0773 0.213 Uiso 1 1 calc R . . C7 C 0.0460(6) 0.4205(9) 0.22510(18) 0.115(3) Uani 1 1 d . . . H7B H 0.1308 0.3772 0.2146 0.137 Uiso 0.56 1 calc PR A 1 H7A H -0.0370 0.4745 0.2239 0.137 Uiso 0.44 1 d PR A 2 C8 C 0.1100(7) 0.5062(6) 0.25562(19) 0.107(2) Uani 1 1 d . A . H8A H 0.1493 0.5884 0.2439 0.161 Uiso 1 1 calc R . . H8B H 0.1823 0.4541 0.2685 0.161 Uiso 1 1 calc R . . H8C H 0.0406 0.5328 0.2746 0.161 Uiso 1 1 calc R . . C9 C -0.0240(6) 0.2965(6) 0.23769(15) 0.0980(18) Uani 1 1 d . A . H9A H -0.0668 0.2522 0.2154 0.147 Uiso 1 1 calc R . . H9B H -0.0943 0.3202 0.2567 0.147 Uiso 1 1 calc R . . H9C H 0.0422 0.2340 0.2495 0.147 Uiso 1 1 calc R . . C10 C 0.0520(5) 0.5390(5) 0.16099(16) 0.0512(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br 0.0589(3) 0.0960(4) 0.0633(3) 0.0152(3) -0.0153(3) -0.0203(3) O1 0.064(3) 0.193(4) 0.056(3) -0.019(3) 0.009(2) -0.020(3) N1 0.041(5) 0.074(5) 0.049(6) -0.001(5) -0.007(5) 0.004(4) N2 0.048(6) 0.067(5) 0.054(6) 0.018(4) 0.006(5) 0.006(4) N3 0.051(5) 0.068(5) 0.049(6) 0.007(4) -0.004(4) -0.014(4) N1' 0.063(8) 0.086(7) 0.018(6) -0.002(6) -0.005(6) 0.011(6) N2' 0.041(6) 0.094(8) 0.057(8) 0.021(7) 0.028(6) 0.023(5) N3' 0.040(6) 0.114(8) 0.052(7) 0.015(6) 0.009(6) 0.016(6) C1 0.134(6) 0.187(8) 0.098(5) -0.033(5) -0.048(5) 0.104(6) C2 0.144(7) 0.129(6) 0.348(13) -0.087(8) 0.136(8) -0.002(6) C3 0.067(4) 0.302(11) 0.146(7) 0.117(7) -0.029(5) -0.071(6) C4 0.063(5) 0.213(8) 0.085(5) 0.016(6) 0.026(4) -0.025(5) C5 0.069(5) 0.163(7) 0.223(9) 0.045(6) -0.049(5) -0.035(4) C6 0.134(7) 0.143(6) 0.149(7) 0.049(5) 0.066(5) 0.046(5) C7 0.068(4) 0.217(8) 0.059(5) 0.061(6) -0.018(4) -0.046(5) C8 0.107(5) 0.112(5) 0.102(5) -0.011(4) 0.020(4) 0.001(4) C9 0.101(5) 0.122(5) 0.070(4) 0.008(4) 0.006(3) -0.001(4) C10 0.038(3) 0.066(3) 0.050(4) -0.002(3) 0.004(3) 0.013(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 1.340(9) . ? N1 C10 1.358(9) . ? N2 C10 1.280(9) . ? N2 C4 1.414(10) . ? N3 C10 1.370(8) . ? N3 C7 1.419(8) . ? N1' C10 1.312(11) . ? N1' C1 1.330(11) . ? N2' C4 1.314(11) . ? N2' C10 1.400(11) . ? N3' C10 1.356(10) . ? N3' C7 1.334(10) . ? C1 C3 1.416(8) . ? C1 C2 1.434(8) . ? C4 C5 1.447(8) . ? C4 C6 1.466(8) . ? C7 C8 1.473(7) . ? C7 C9 1.445(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 C1 N1 C10 134.7(9) . . ? C10 N2 C4 136.7(8) . . ? C10 N3 C7 125.4(7) . . ? C10 N1' C1 140.9(11) . . ? C4 N2' C10 134.7(10) . . ? C10 N3' C7 134.3(9) . . ? N1 C1 N1' 42.2(4) . . ? N1 C1 C3 109.2(7) . . ? N1' C1 C3 140.7(8) . . ? N1 C1 C2 127.5(8) . . ? N1' C1 C2 99.1(8) . . ? C3 C1 C2 119.2(7) . . ? N2' C4 N2 42.3(5) . . ? N2' C4 C5 131.8(8) . . ? N2 C4 C5 111.3(6) . . ? N2' C4 C6 108.7(8) . . ? N2 C4 C6 125.7(7) . . ? C5 C4 C6 117.3(6) . . ? N3' C7 N3 47.8(4) . . ? N3' C7 C8 103.7(7) . . ? N3 C7 C8 128.5(7) . . ? N3' C7 C9 136.8(8) . . ? N3 C7 C9 108.0(6) . . ? C8 C7 C9 117.0(5) . . ? N2 C10 N1' 156.9(8) . . ? N2 C10 N3' 73.2(6) . . ? N1' C10 N3' 121.9(8) . . ? N2 C10 N3 120.1(7) . . ? N1' C10 N3 79.9(7) . . ? N3' C10 N3 48.4(5) . . ? N2 C10 N1 122.9(7) . . ? N1' C10 N1 42.2(4) . . ? N3' C10 N1 163.7(7) . . ? N3 C10 N1 116.4(6) . . ? N2 C10 N2' 43.0(4) . . ? N1' C10 N2' 119.7(8) . . ? N3' C10 N2' 116.1(8) . . ? N3 C10 N2' 159.3(7) . . ? N1 C10 N2' 80.1(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 C10 N1 C1 N1' -2.4(9) . . . . ? C10 N1 C1 C3 -149.1(8) . . . . ? C10 N1 C1 C2 54.3(15) . . . . ? C10 N1' C1 N1 2.8(10) . . . . ? C10 N1' C1 C3 58(2) . . . . ? C10 N1' C1 C2 -135.0(13) . . . . ? C10 N2' C4 N2 15.5(9) . . . . ? C10 N2' C4 C5 -59.4(18) . . . . ? C10 N2' C4 C6 138.5(11) . . . . ? C10 N2 C4 N2' -17.7(10) . . . . ? C10 N2 C4 C5 111.8(11) . . . . ? C10 N2 C4 C6 -95.9(12) . . . . ? C10 N3' C7 N3 18.6(9) . . . . ? C10 N3' C7 C8 -111.6(11) . . . . ? C10 N3' C7 C9 87.8(14) . . . . ? C10 N3 C7 N3' -16.1(8) . . . . ? C10 N3 C7 C8 55.7(11) . . . . ? C10 N3 C7 C9 -153.8(6) . . . . ? C4 N2 C10 N1' -32(2) . . . . ? C4 N2 C10 N3' -166.3(11) . . . . ? C4 N2 C10 N3 -179.0(8) . . . . ? C4 N2 C10 N1 10.9(14) . . . . ? C4 N2 C10 N2' 16.3(9) . . . . ? C1 N1' C10 N2 56(3) . . . . ? C1 N1' C10 N3' -178.2(12) . . . . ? C1 N1' C10 N3 -153.1(15) . . . . ? C1 N1' C10 N1 -2.8(10) . . . . ? C1 N1' C10 N2' 19.7(18) . . . . ? C7 N3' C10 N2 175.6(13) . . . . ? C7 N3' C10 N1' 14.9(15) . . . . ? C7 N3' C10 N3 -19.1(9) . . . . ? C7 N3' C10 N1 4(3) . . . . ? C7 N3' C10 N2' 177.7(11) . . . . ? C7 N3 C10 N2 31.9(10) . . . . ? C7 N3 C10 N1' -135.5(9) . . . . ? C7 N3 C10 N3' 15.6(7) . . . . ? C7 N3 C10 N1 -157.3(8) . . . . ? C7 N3 C10 N2' 63(2) . . . . ? C1 N1 C10 N2 -154.2(9) . . . . ? C1 N1 C10 N1' 2.4(9) . . . . ? C1 N1 C10 N3' 16(3) . . . . ? C1 N1 C10 N3 35.4(12) . . . . ? C1 N1 C10 N2' -157.9(11) . . . . ? C4 N2' C10 N2 -17.0(10) . . . . ? C4 N2' C10 N1' 143.3(12) . . . . ? C4 N2' C10 N3' -19.8(16) . . . . ? C4 N2' C10 N3 -57(3) . . . . ? C4 N2' C10 N1 158.4(14) . . . . ? 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 H1 Br 0.82(4) 2.56(4) 3.369(4) 168(5) 5_445 O1 H2 Br 0.84(4) 2.47(4) 3.305(4) 172(5) 3 N1 H1A Br 0.87 2.84 3.596(9) 146.0 . N2 H2A Br 0.87 2.74 3.559(8) 157.1 5_545 N3 H3A O1 0.87 2.27 2.969(9) 137.2 . N2' H2'D Br 0.87 2.79 3.537(11) 145.4 . N3' H3'D Br 0.87 2.70 3.497(9) 153.1 5_545 _diffrn_measured_fraction_theta_max 0.867 _diffrn_reflns_theta_full 28.96 _diffrn_measured_fraction_theta_full 0.867 _refine_diff_density_max 0.236 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.052