#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2009122.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2009122 loop_ _publ_author_name 'I\,sik, \,S.' '\"Ozt\"urk, S.' 'Fun, H.-K.' 'Agar, E.' '\,Sa\,smaz, S.' _publ_section_title ; 10,11-Dibromo-3,6-ditosyl-3,6-diazabicyclo[6.4.0]dodeca-1(8),9,11-triene ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1850 _journal_page_last 1852 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C24 H24 Br2 N2 O4 S2' _chemical_formula_weight 628.39 _chemical_name_systematic ; 10,11-Dibromo-3,6-ditosyl-3,6-diazabicyclo[6.4.0]dodeca-1(8),9,11-triene ; _space_group_IT_number 92 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall 'P 4abw 2nw' _symmetry_space_group_name_H-M 'P 41 21 2' _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.44750(10) _cell_length_b 10.44750(10) _cell_length_c 22.8183(2) _cell_measurement_reflns_used 7264 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 33.20 _cell_measurement_theta_min 2.64 _cell_volume 2490.62(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Sheldrick, 1995)' _computing_publication_material 'SHELXTL and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.068 _diffrn_reflns_av_sigmaI/netI 0.068 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 22912 _diffrn_reflns_theta_full 33.18 _diffrn_reflns_theta_max 33.18 _diffrn_reflns_theta_min 2.64 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 3.46 _exptl_absorpt_correction_T_max 0.501 _exptl_absorpt_correction_T_min 0.325 _exptl_absorpt_correction_type 'empirical using SADABS (Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 1264 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.39 _refine_diff_density_min -0.34 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.003(8) _refine_ls_extinction_coef 0.0001(5) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 4721 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.010 _refine_ls_R_factor_all 0.128 _refine_ls_R_factor_gt 0.060 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0464P)^2^+3.5783P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.141 _reflns_number_gt 2635 _reflns_number_total 4721 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fr1214.cif _[local]_cod_data_source_block I _cod_database_code 2009122 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol Br1 0.04476(6) 0.15878(5) 0.06404(3) 0.05399(19) Uani d . 1 Br N1 -0.4179(4) -0.2432(4) 0.02261(17) 0.0391(9) Uani d . 1 N S1 -0.52505(13) -0.14329(13) -0.00104(5) 0.0448(3) Uani d . 1 S O1 -0.4703(4) -0.0186(4) 0.0037(2) 0.0677(12) Uani d . 1 O O2 -0.5668(4) -0.1908(5) -0.05674(15) 0.0710(13) Uani d . 1 O C1 -0.4507(5) -0.3791(5) 0.0235(2) 0.0422(11) Uani d . 1 C C2 -0.3106(5) -0.1995(6) 0.0588(2) 0.0430(12) Uani d . 1 C C3 -0.1964(4) -0.1456(5) 0.02582(19) 0.0362(10) Uani d . 1 C C4 -0.1373(4) -0.0399(5) 0.05092(19) 0.0395(10) Uani d . 1 C C5 -0.0310(5) 0.0173(4) 0.0257(2) 0.0373(10) Uani d . 1 C C6 -0.6547(5) -0.1560(5) 0.04804(18) 0.0367(9) Uani d . 1 C C7 -0.6507(6) -0.0914(5) 0.1012(2) 0.0453(12) Uani d . 1 C C8 -0.7480(6) -0.1090(5) 0.1410(2) 0.0484(13) Uani d . 1 C C9 -0.8495(5) -0.1915(5) 0.1297(2) 0.0446(12) Uani d . 1 C C10 -0.8521(5) -0.2535(5) 0.0757(2) 0.0495(12) Uani d D 1 C C11 -0.7564(5) -0.2365(6) 0.0352(2) 0.0473(12) Uani d D 1 C C12 -0.9534(6) -0.2136(6) 0.1736(3) 0.0686(18) Uani d . 1 C H12A -0.9231 -0.2706 0.2035 0.103 Uiso calc R 1 H H12B -1.0263 -0.2508 0.1545 0.103 Uiso calc R 1 H H12C -0.9775 -0.1335 0.1911 0.103 Uiso calc R 1 H H1A -0.547(4) -0.392(4) 0.0182(18) 0.026(11) Uiso d . 1 H H1B -0.421(6) -0.414(6) 0.057(3) 0.060(18) Uiso d . 1 H H2A -0.282(5) -0.263(6) 0.080(2) 0.044(16) Uiso d . 1 H H2B -0.344(5) -0.131(6) 0.086(2) 0.055(16) Uiso d . 1 H H4 -0.173(5) 0.003(5) 0.087(2) 0.051(15) Uiso d . 1 H H7 -0.582(6) -0.033(6) 0.109(3) 0.059(17) Uiso d . 1 H H8 -0.748(5) -0.073(5) 0.177(2) 0.053(15) Uiso d . 1 H H10 -0.921(4) -0.306(5) 0.067(3) 0.08(2) Uiso d D 1 H H11 -0.762(7) -0.283(6) 0.0008(19) 0.09(2) Uiso d D 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.0590(4) 0.0472(3) 0.0558(3) -0.0123(3) -0.0088(3) -0.0070(3) N1 0.034(2) 0.040(2) 0.043(2) -0.0009(17) 0.0025(16) -0.0037(17) S1 0.0484(7) 0.0493(7) 0.0368(6) 0.0085(6) 0.0105(5) 0.0056(5) O1 0.072(3) 0.044(2) 0.088(3) 0.007(2) 0.034(3) 0.014(2) O2 0.070(3) 0.111(4) 0.0314(19) 0.022(3) 0.0021(18) 0.002(2) C1 0.040(3) 0.036(2) 0.051(3) -0.001(2) 0.005(2) -0.004(2) C2 0.045(3) 0.052(3) 0.033(2) -0.009(2) 0.003(2) -0.007(2) C3 0.039(2) 0.039(2) 0.032(2) 0.000(2) 0.0001(17) -0.0007(19) C4 0.040(2) 0.043(3) 0.036(2) 0.001(2) -0.0015(18) -0.004(2) C5 0.038(2) 0.035(2) 0.039(2) -0.0019(19) -0.0084(19) -0.0020(18) C6 0.042(2) 0.036(2) 0.032(2) 0.010(2) 0.0014(18) 0.0031(18) C7 0.055(3) 0.037(3) 0.044(3) 0.000(3) 0.004(2) -0.005(2) C8 0.064(3) 0.044(3) 0.037(3) 0.007(3) 0.010(2) -0.005(2) C9 0.045(3) 0.039(3) 0.050(3) 0.011(2) 0.008(2) 0.010(2) C10 0.040(3) 0.052(3) 0.057(3) 0.006(3) -0.001(2) -0.003(2) C11 0.044(3) 0.057(3) 0.041(3) 0.013(2) -0.005(2) -0.007(2) C12 0.074(4) 0.063(4) 0.069(4) 0.000(3) 0.029(4) 0.003(3) 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' S S 0.1246 0.1234 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C2 . . 118.3(4) ? C1 N1 S1 . . 117.9(3) ? C2 N1 S1 . . 121.0(4) ? O1 S1 O2 . . 120.4(3) yes O1 S1 N1 . . 106.6(3) yes O2 S1 N1 . . 106.4(2) yes O1 S1 C6 . . 109.2(2) ? O2 S1 C6 . . 107.7(2) ? N1 S1 C6 . . 105.7(2) ? N1 C1 C1 . 7 110.8(3) ? N1 C1 H1A . . 111(2) ? C1 C1 H1A 7 . 110(2) ? N1 C1 H1B . . 109(4) ? C1 C1 H1B 7 . 104(4) ? H1A C1 H1B . . 112(4) ? N1 C2 C3 . . 116.0(4) ? N1 C2 H2A . . 110(4) ? C3 C2 H2A . . 106(4) ? N1 C2 H2B . . 108(3) ? C3 C2 H2B . . 108(3) ? H2A C2 H2B . . 108(5) ? C4 C3 C3 . 7 118.8(3) ? C4 C3 C2 . . 116.1(4) ? C3 C3 C2 7 . 125.1(3) ? C5 C4 C3 . . 121.8(4) ? C5 C4 H4 . . 117(3) ? C3 C4 H4 . . 122(3) ? C5 C5 C4 7 . 119.4(3) ? C5 C5 Br1 7 . 121.92(15) ? C4 C5 Br1 . . 118.7(3) ? C11 C6 C7 . . 120.2(5) ? C11 C6 S1 . . 120.0(4) ? C7 C6 S1 . . 119.7(4) ? C8 C7 C6 . . 119.4(5) ? C8 C7 H7 . . 121(4) ? C6 C7 H7 . . 120(4) ? C7 C8 C9 . . 121.5(5) ? C7 C8 H8 . . 123(4) ? C9 C8 H8 . . 115(4) ? C8 C9 C10 . . 117.9(5) ? C8 C9 C12 . . 121.6(5) yes C10 C9 C12 . . 120.5(5) ? C11 C10 C9 . . 121.4(6) ? C11 C10 H10 . . 120(4) ? C9 C10 H10 . . 118(4) ? C10 C11 C6 . . 119.6(5) ? C10 C11 H11 . . 117(5) ? C6 C11 H11 . . 123(5) ? C9 C12 H12A . . 109.5 ? C9 C12 H12B . . 109.5 ? H12A C12 H12B . . 109.5 ? C9 C12 H12C . . 109.5 ? H12A C12 H12C . . 109.5 ? H12B C12 H12C . . 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 C5 . 1.892(4) yes N1 C1 . 1.461(6) yes N1 C2 . 1.465(6) yes N1 S1 . 1.623(4) yes S1 O1 . 1.427(4) yes S1 O2 . 1.432(4) yes S1 C6 . 1.763(5) yes C1 C1 7 1.508(9) ? C1 H1A . 1.02(4) ? C1 H1B . 0.90(6) ? C2 C3 . 1.519(7) ? C2 H2A . 0.87(6) ? C2 H2B . 1.02(6) ? C3 C4 . 1.389(7) ? C3 C3 7 1.397(9) ? C4 C5 . 1.386(7) ? C4 H4 . 1.01(5) ? C5 C5 7 1.372(9) ? C6 C11 . 1.386(8) ? C6 C7 . 1.389(7) ? C7 C8 . 1.376(8) ? C7 H7 . 0.96(6) ? C8 C9 . 1.391(8) ? C8 H8 . 0.91(6) ? C9 C10 . 1.393(7) ? C9 C12 . 1.496(7) ? C10 C11 . 1.373(8) ? C10 H10 . 0.92(2) ? C11 H11 . 0.93(2) ? C12 H12A . 0.9600 ? C12 H12B . 0.9600 ? C12 H12C . 0.9600 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C2 H2B O2 3_455 1.01(6) 2.56(5) 3.367(6) 136(4) yes C10 H10 O1 7_455 0.930(10) 2.57(6) 3.382(7) 147(5) yes C2 H2B O1 1_555 1.02(6) 2.60(5) 2.818(8) 91(3) no C11 H11 O2 1_555 0.93(2) 2.61(7) 2.922(7) 99(5) no C7 H7 O1 1_555 0.96(6) 2.70(5) 3.012(7) 100(4) no C1 H1A O2 1_555 1.02(4) 2.71(4) 2.950(7) 93(2) no 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion C1 N1 S1 O1 . . 178.9(4) C2 N1 S1 O1 . . 18.1(4) C1 N1 S1 O2 . . -51.5(4) C2 N1 S1 O2 . . 147.7(4) C1 N1 S1 C6 . . 62.8(4) C2 N1 S1 C6 . . -98.0(4) C2 N1 C1 C1 . 7 -90.5(6) S1 N1 C1 C1 . 7 108.2(5) C1 N1 C2 C3 . . 115.8(5) S1 N1 C2 C3 . . -83.5(5) N1 C2 C3 C4 . . 141.0(5) N1 C2 C3 C3 . 7 -41.0(9) C3 C3 C4 C5 7 . 0.9(8) C2 C3 C4 C5 . . 179.1(5) C3 C4 C5 C5 . 7 0.4(8) C3 C4 C5 Br1 . . -178.7(4) O1 S1 C6 C11 . . 150.6(4) O2 S1 C6 C11 . . 18.3(5) N1 S1 C6 C11 . . -95.1(4) O1 S1 C6 C7 . . -33.4(5) O2 S1 C6 C7 . . -165.7(4) N1 S1 C6 C7 . . 80.9(4) C11 C6 C7 C8 . . 0.6(8) S1 C6 C7 C8 . . -175.4(4) C6 C7 C8 C9 . . 0.9(8) C7 C8 C9 C10 . . -1.9(8) C7 C8 C9 C12 . . 178.3(5) C8 C9 C10 C11 . . 1.5(8) C12 C9 C10 C11 . . -178.7(5) C9 C10 C11 C6 . . 0.0(8) C7 C6 C11 C10 . . -1.0(8) S1 C6 C11 C10 . . 175.0(4)