# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_tr1 _database_code_depnum_ccdc_archive 'CCDC 924191' #TrackingRef 'Kiran 2l.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H4 Cl N O2' _chemical_formula_sum 'C8 H4 Cl N O2' _chemical_formula_weight 181.57 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 P2(1)/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 12.337(3) _cell_length_b 3.8023(10) _cell_length_c 15.603(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.168(4) _cell_angle_gamma 90.00 _cell_volume 722.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5115 _cell_measurement_theta_min 3.35 _cell_measurement_theta_max 28.35 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.490 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.160 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.474 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 0.927 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7021 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.41 _reflns_number_total 1788 _reflns_number_gt 1690 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0352P)^2^+0.3486P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.006(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1788 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0729 _refine_ls_wR_factor_gt 0.0719 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.75907(2) 0.13514(8) 1.161819(16) 0.02125(11) Uani 1 1 d . . . O1 O 0.64181(7) -0.0244(3) 0.78740(5) 0.0241(2) Uani 1 1 d . . . O2 O 0.52038(7) 0.2686(3) 0.86237(5) 0.0228(2) Uani 1 1 d . . . N1 N 0.98860(9) -0.3081(3) 1.09453(7) 0.0240(2) Uani 1 1 d . . . C1 C 0.53405(10) 0.1275(4) 0.77871(8) 0.0228(3) Uani 1 1 d . . . H1 H 0.4787 -0.0501 0.7605 0.027 Uiso 1 1 calc R . . H2 H 0.5264 0.3131 0.7355 0.027 Uiso 1 1 calc R . . C2 C 0.68387(9) -0.0118(3) 0.87411(7) 0.0163(2) Uani 1 1 d . . . C3 C 0.78289(9) -0.1375(3) 0.91535(7) 0.0163(2) Uani 1 1 d . . . H3 H 0.8322 -0.2498 0.8852 0.020 Uiso 1 1 calc R . . C4 C 0.80596(9) -0.0869(3) 1.00623(7) 0.0148(2) Uani 1 1 d . . . C5 C 0.90827(9) -0.2108(3) 1.05465(7) 0.0173(2) Uani 1 1 d . . . C6 C 0.73012(9) 0.0794(3) 1.05041(7) 0.0149(2) Uani 1 1 d . . . C7 C 0.62963(9) 0.2069(3) 1.00734(7) 0.0161(2) Uani 1 1 d . . . H4 H 0.5792 0.3175 1.0367 0.019 Uiso 1 1 calc R . . C8 C 0.61013(9) 0.1586(3) 0.91903(7) 0.0161(2) 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 Cl1 0.02498(17) 0.02612(19) 0.01228(15) -0.00192(10) 0.00180(10) -0.00065(11) O1 0.0194(4) 0.0387(6) 0.0130(4) -0.0032(4) -0.0009(3) 0.0066(4) O2 0.0183(4) 0.0331(5) 0.0157(4) -0.0016(4) -0.0014(3) 0.0078(4) N1 0.0209(5) 0.0294(6) 0.0211(5) 0.0039(4) 0.0016(4) 0.0018(4) C1 0.0225(6) 0.0282(7) 0.0163(5) -0.0021(4) -0.0016(4) 0.0060(5) C2 0.0176(5) 0.0188(6) 0.0124(5) -0.0012(4) 0.0022(4) -0.0017(4) C3 0.0157(5) 0.0184(6) 0.0156(5) -0.0011(4) 0.0044(4) -0.0002(4) C4 0.0136(5) 0.0149(5) 0.0156(5) 0.0015(4) 0.0010(4) -0.0015(4) C5 0.0185(5) 0.0181(6) 0.0155(5) 0.0007(4) 0.0034(4) -0.0024(4) C6 0.0176(5) 0.0149(5) 0.0122(4) -0.0002(4) 0.0019(4) -0.0031(4) C7 0.0163(5) 0.0161(5) 0.0164(5) -0.0009(4) 0.0040(4) 0.0002(4) C8 0.0141(5) 0.0167(6) 0.0169(5) 0.0009(4) 0.0007(4) 0.0003(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 Cl1 C6 1.7310(12) . ? O1 C2 1.3706(13) . ? O1 C1 1.4360(15) . ? O2 C8 1.3677(13) . ? O2 C1 1.4458(15) . ? N1 C5 1.1445(15) . ? C1 H1 0.9700 . ? C1 H2 0.9700 . ? C2 C3 1.3728(15) . ? C2 C8 1.3936(16) . ? C3 C4 1.4142(15) . ? C3 H3 0.9300 . ? C4 C6 1.3986(16) . ? C4 C5 1.4429(15) . ? C6 C7 1.3994(15) . ? C7 C8 1.3728(16) . ? C7 H4 0.9300 . ? 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 O1 C1 106.16(9) . . ? C8 O2 C1 105.74(9) . . ? O1 C1 O2 107.67(9) . . ? O1 C1 H1 110.2 . . ? O2 C1 H1 110.2 . . ? O1 C1 H2 110.2 . . ? O2 C1 H2 110.2 . . ? H1 C1 H2 108.5 . . ? O1 C2 C3 128.26(10) . . ? O1 C2 C8 109.75(10) . . ? C3 C2 C8 121.98(10) . . ? C2 C3 C4 116.39(10) . . ? C2 C3 H3 121.8 . . ? C4 C3 H3 121.8 . . ? C6 C4 C3 120.81(10) . . ? C6 C4 C5 119.18(10) . . ? C3 C4 C5 120.01(10) . . ? N1 C5 C4 178.65(12) . . ? C4 C6 C7 122.07(10) . . ? C4 C6 Cl1 120.21(8) . . ? C7 C6 Cl1 117.72(8) . . ? C8 C7 C6 115.84(10) . . ? C8 C7 H4 122.1 . . ? C6 C7 H4 122.1 . . ? O2 C8 C7 127.04(10) . . ? O2 C8 C2 110.07(10) . . ? C7 C8 C2 122.88(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 O1 C1 O2 6.95(13) . . . . ? C8 O2 C1 O1 -7.93(13) . . . . ? C1 O1 C2 C3 177.30(12) . . . . ? C1 O1 C2 C8 -3.37(14) . . . . ? O1 C2 C3 C4 179.66(11) . . . . ? C8 C2 C3 C4 0.40(17) . . . . ? C2 C3 C4 C6 0.70(17) . . . . ? C2 C3 C4 C5 -179.94(11) . . . . ? C6 C4 C5 N1 13(6) . . . . ? C3 C4 C5 N1 -166(6) . . . . ? C3 C4 C6 C7 -0.92(18) . . . . ? C5 C4 C6 C7 179.72(11) . . . . ? C3 C4 C6 Cl1 179.34(8) . . . . ? C5 C4 C6 Cl1 -0.02(15) . . . . ? C4 C6 C7 C8 -0.01(17) . . . . ? Cl1 C6 C7 C8 179.74(9) . . . . ? C1 O2 C8 C7 -175.03(12) . . . . ? C1 O2 C8 C2 5.96(13) . . . . ? C6 C7 C8 O2 -177.76(11) . . . . ? C6 C7 C8 C2 1.14(18) . . . . ? O1 C2 C8 O2 -1.71(14) . . . . ? C3 C2 C8 O2 177.68(11) . . . . ? O1 C2 C8 C7 179.23(11) . . . . ? C3 C2 C8 C7 -1.39(19) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.352 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.051 data_4c _database_code_depnum_ccdc_archive 'CCDC 924192' #TrackingRef 'Kiran 4f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Br2 N2 O4' _chemical_formula_weight 456.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2030(10) _cell_length_b 9.5004(12) _cell_length_c 12.9717(16) _cell_angle_alpha 85.645(3) _cell_angle_beta 89.563(3) _cell_angle_gamma 70.248(3) _cell_volume 832.88(19) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour brown _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 4.889 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5084 _exptl_absorpt_correction_T_max 0.6153 _exptl_absorpt_process_details 'multi-scan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13496 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 28.53 _reflns_number_total 4127 _reflns_number_gt 3572 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+0.4897P] 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_number_reflns 4127 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0613 _refine_ls_wR_factor_gt 0.0592 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.51441(3) 0.71344(2) 0.492029(14) 0.02515(7) Uani 1 1 d . . . Br2 Br 1.28047(3) -0.07035(2) 0.218131(16) 0.02694(7) Uani 1 1 d . . . O1 O 0.2458(2) 1.00093(16) 0.80843(11) 0.0242(3) Uani 1 1 d . . . O2 O 0.2865(2) 0.97539(17) 0.60957(11) 0.0252(3) Uani 1 1 d . . . H2 H 0.234(4) 1.032(3) 0.640(2) 0.038 Uiso 1 1 d . . . O3 O 1.0486(2) 0.21868(17) 0.09773(11) 0.0258(3) Uani 1 1 d . . . H7 H 0.992(4) 0.279(3) 0.071(2) 0.039 Uiso 1 1 d . . . O4 O 0.8369(2) 0.48126(15) 0.16199(11) 0.0266(3) Uani 1 1 d . . . N1 N 0.7798(3) 0.3899(2) 0.93655(16) 0.0404(5) Uani 1 1 d . . . N2 N 0.9854(3) 0.2888(2) 0.60820(14) 0.0274(4) Uani 1 1 d . . . C1 C 0.2160(3) 1.0235(3) 0.91510(16) 0.0269(5) Uani 1 1 d . . . H3 H 0.1743 0.9455 0.9480 0.040 Uiso 1 1 calc R . . H4 H 0.1163 1.1191 0.9226 0.040 Uiso 1 1 calc R . . H1 H 0.3371 1.0211 0.9468 0.040 Uiso 1 1 calc R . . C2 C 0.3687(3) 0.8653(2) 0.78272(15) 0.0190(4) Uani 1 1 d . . . C3 C 0.4697(3) 0.7443(2) 0.84949(15) 0.0209(4) Uani 1 1 d . . . H6 H 0.4588 0.7502 0.9206 0.025 Uiso 1 1 calc R . . C4 C 0.5892(3) 0.6122(2) 0.80866(15) 0.0205(4) Uani 1 1 d . . . C5 C 0.6961(3) 0.4868(3) 0.87902(17) 0.0289(5) Uani 1 1 d . . . C6 C 0.3853(3) 0.8555(2) 0.67502(14) 0.0182(4) Uani 1 1 d . . . C7 C 0.6066(3) 0.5999(2) 0.70267(15) 0.0204(4) Uani 1 1 d . . . H5 H 0.6861 0.5114 0.6765 0.024 Uiso 1 1 calc R . . C8 C 0.5023(3) 0.7231(2) 0.63683(14) 0.0171(4) Uani 1 1 d . . . C9 C 1.0340(3) 0.2351(2) 0.20004(14) 0.0182(4) Uani 1 1 d . . . C10 C 0.9233(3) 0.3728(2) 0.23807(14) 0.0179(4) Uani 1 1 d . . . C11 C 0.9096(3) 0.3879(2) 0.34306(15) 0.0185(4) Uani 1 1 d . . . H11 H 0.8362 0.4789 0.3683 0.022 Uiso 1 1 calc R . . C12 C 1.0083(3) 0.2636(2) 0.41095(14) 0.0183(4) Uani 1 1 d . . . C13 C 0.9941(3) 0.2782(2) 0.52093(15) 0.0204(4) Uani 1 1 d . . . C14 C 0.7279(3) 0.6242(2) 0.1903(2) 0.0324(5) Uani 1 1 d . . . H8 H 0.6200 0.6188 0.2324 0.049 Uiso 1 1 calc R . . H9 H 0.6776 0.6897 0.1293 0.049 Uiso 1 1 calc R . . H12 H 0.8112 0.6626 0.2287 0.049 Uiso 1 1 calc R . . C15 C 1.1205(3) 0.1267(2) 0.37544(15) 0.0191(4) Uani 1 1 d . . . H10 H 1.1860 0.0452 0.4214 0.023 Uiso 1 1 calc R . . C16 C 1.1318(3) 0.1151(2) 0.26962(15) 0.0183(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02781(12) 0.03206(12) 0.01541(10) -0.00606(8) 0.00350(8) -0.00909(9) Br2 0.03046(13) 0.01916(11) 0.02364(11) -0.00601(8) 0.00118(9) 0.00240(8) O1 0.0277(8) 0.0225(7) 0.0178(7) -0.0053(6) 0.0044(6) -0.0018(6) O2 0.0311(9) 0.0192(7) 0.0187(7) 0.0017(6) -0.0011(6) -0.0004(6) O3 0.0332(9) 0.0231(8) 0.0139(7) -0.0031(6) -0.0015(6) 0.0005(6) O4 0.0358(9) 0.0170(7) 0.0208(7) 0.0001(6) -0.0036(6) -0.0012(6) N1 0.0477(13) 0.0344(11) 0.0261(10) 0.0043(9) -0.0042(9) 0.0017(9) N2 0.0289(10) 0.0292(10) 0.0219(9) -0.0060(7) 0.0025(7) -0.0060(8) C1 0.0312(12) 0.0294(11) 0.0204(10) -0.0103(8) 0.0077(9) -0.0091(9) C2 0.0173(10) 0.0207(10) 0.0190(9) -0.0041(7) 0.0028(7) -0.0059(7) C3 0.0216(10) 0.0257(10) 0.0152(9) -0.0002(7) 0.0012(8) -0.0082(8) C4 0.0194(10) 0.0211(10) 0.0191(9) 0.0035(7) -0.0020(8) -0.0052(7) C5 0.0302(12) 0.0288(11) 0.0234(10) 0.0005(9) -0.0002(9) -0.0047(9) C6 0.0173(10) 0.0202(9) 0.0170(9) 0.0017(7) 0.0004(7) -0.0070(7) C7 0.0171(10) 0.0200(9) 0.0228(10) -0.0020(8) 0.0021(8) -0.0047(7) C8 0.0175(10) 0.0211(9) 0.0138(8) -0.0009(7) 0.0018(7) -0.0079(7) C9 0.0186(10) 0.0201(9) 0.0153(8) -0.0044(7) 0.0018(7) -0.0051(7) C10 0.0172(10) 0.0173(9) 0.0186(9) -0.0013(7) -0.0010(7) -0.0048(7) C11 0.0180(10) 0.0178(9) 0.0197(9) -0.0057(7) 0.0024(7) -0.0052(7) C12 0.0171(10) 0.0213(9) 0.0172(9) -0.0062(7) 0.0020(7) -0.0064(7) C13 0.0189(10) 0.0199(10) 0.0208(10) -0.0035(8) 0.0004(8) -0.0041(7) C14 0.0335(13) 0.0138(10) 0.0453(14) 0.0105(9) -0.0151(11) -0.0043(8) C15 0.0176(10) 0.0202(10) 0.0181(9) -0.0027(7) 0.0000(7) -0.0043(7) C16 0.0163(9) 0.0173(9) 0.0196(9) -0.0063(7) 0.0005(7) -0.0026(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C8 1.8875(18) . ? Br2 C16 1.8947(18) . ? O1 C2 1.358(2) . ? O1 C1 1.420(2) . ? O2 C6 1.356(2) . ? O2 H2 0.69(3) . ? O3 C9 1.347(2) . ? O3 H7 0.66(3) . ? O4 C10 1.358(2) . ? O4 C14 1.395(3) . ? N1 C5 1.139(3) . ? N2 C13 1.143(3) . ? C1 H3 0.9600 . ? C1 H4 0.9600 . ? C1 H1 0.9600 . ? C2 C3 1.376(3) . ? C2 C6 1.409(3) . ? C3 C4 1.400(3) . ? C3 H6 0.9300 . ? C4 C7 1.390(3) . ? C4 C5 1.439(3) . ? C6 C8 1.382(3) . ? C7 C8 1.389(3) . ? C7 H5 0.9300 . ? C9 C16 1.386(3) . ? C9 C10 1.406(3) . ? C10 C11 1.380(3) . ? C11 C12 1.400(3) . ? C11 H11 0.9300 . ? C12 C15 1.390(3) . ? C12 C13 1.443(3) . ? C14 H8 0.9600 . ? C14 H9 0.9600 . ? C14 H12 0.9600 . ? C15 C16 1.385(3) . ? C15 H10 0.9300 . ? 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 O1 C1 117.85(16) . . ? C6 O2 H2 107(2) . . ? C9 O3 H7 111(3) . . ? C10 O4 C14 118.27(16) . . ? O1 C1 H3 109.5 . . ? O1 C1 H4 109.5 . . ? H3 C1 H4 109.5 . . ? O1 C1 H1 109.5 . . ? H3 C1 H1 109.5 . . ? H4 C1 H1 109.5 . . ? O1 C2 C3 126.97(17) . . ? O1 C2 C6 112.78(17) . . ? C3 C2 C6 120.25(18) . . ? C2 C3 C4 118.98(18) . . ? C2 C3 H6 120.5 . . ? C4 C3 H6 120.5 . . ? C7 C4 C3 121.67(18) . . ? C7 C4 C5 119.71(19) . . ? C3 C4 C5 118.61(18) . . ? N1 C5 C4 178.4(2) . . ? O2 C6 C8 120.43(17) . . ? O2 C6 C2 120.02(18) . . ? C8 C6 C2 119.55(17) . . ? C8 C7 C4 118.30(18) . . ? C8 C7 H5 120.9 . . ? C4 C7 H5 120.9 . . ? C6 C8 C7 121.24(17) . . ? C6 C8 Br1 118.06(14) . . ? C7 C8 Br1 120.69(14) . . ? O3 C9 C16 119.71(17) . . ? O3 C9 C10 121.28(17) . . ? C16 C9 C10 119.01(17) . . ? O4 C10 C11 126.31(17) . . ? O4 C10 C9 113.08(16) . . ? C11 C10 C9 120.61(17) . . ? C10 C11 C12 118.72(17) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? C15 C12 C11 121.86(17) . . ? C15 C12 C13 119.07(18) . . ? C11 C12 C13 119.07(17) . . ? N2 C13 C12 179.1(2) . . ? O4 C14 H8 109.5 . . ? O4 C14 H9 109.5 . . ? H8 C14 H9 109.5 . . ? O4 C14 H12 109.5 . . ? H8 C14 H12 109.5 . . ? H9 C14 H12 109.5 . . ? C16 C15 C12 118.08(18) . . ? C16 C15 H10 121.0 . . ? C12 C15 H10 121.0 . . ? C15 C16 C9 121.71(17) . . ? C15 C16 Br2 119.38(14) . . ? C9 C16 Br2 118.90(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 C1 O1 C2 C3 0.2(3) . . . . ? C1 O1 C2 C6 179.40(18) . . . . ? O1 C2 C3 C4 179.39(19) . . . . ? C6 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C7 -0.6(3) . . . . ? C2 C3 C4 C5 179.2(2) . . . . ? C7 C4 C5 N1 166(9) . . . . ? C3 C4 C5 N1 -13(10) . . . . ? O1 C2 C6 O2 1.2(3) . . . . ? C3 C2 C6 O2 -179.56(19) . . . . ? O1 C2 C6 C8 -178.71(17) . . . . ? C3 C2 C6 C8 0.6(3) . . . . ? C3 C4 C7 C8 0.2(3) . . . . ? C5 C4 C7 C8 -179.66(19) . . . . ? O2 C6 C8 C7 179.12(18) . . . . ? C2 C6 C8 C7 -1.0(3) . . . . ? O2 C6 C8 Br1 -1.5(3) . . . . ? C2 C6 C8 Br1 178.34(14) . . . . ? C4 C7 C8 C6 0.6(3) . . . . ? C4 C7 C8 Br1 -178.71(15) . . . . ? C14 O4 C10 C11 2.2(3) . . . . ? C14 O4 C10 C9 -178.10(18) . . . . ? O3 C9 C10 O4 0.2(3) . . . . ? C16 C9 C10 O4 179.32(18) . . . . ? O3 C9 C10 C11 179.95(18) . . . . ? C16 C9 C10 C11 -1.0(3) . . . . ? O4 C10 C11 C12 179.83(19) . . . . ? C9 C10 C11 C12 0.1(3) . . . . ? C10 C11 C12 C15 0.6(3) . . . . ? C10 C11 C12 C13 -179.74(18) . . . . ? C15 C12 C13 N2 42(14) . . . . ? C11 C12 C13 N2 -138(14) . . . . ? C11 C12 C15 C16 -0.4(3) . . . . ? C13 C12 C15 C16 179.88(18) . . . . ? C12 C15 C16 C9 -0.4(3) . . . . ? C12 C15 C16 Br2 -179.22(15) . . . . ? O3 C9 C16 C15 -179.78(18) . . . . ? C10 C9 C16 C15 1.1(3) . . . . ? O3 C9 C16 Br2 -1.0(3) . . . . ? C10 C9 C16 Br2 179.91(14) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 28.53 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 1.059 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.073