data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year 2011 _journal_volume 35 _journal_page_first 1615 _publ_contact_author_name 'Rajesh Gonnade' _publ_contact_author_email rg.gonnade@ncl.res.in loop_ _publ_author_name S.B.Zaware R.G.Gonnade 'D. Srinivas' A.Khan S.Y.Rane data_chloro_lawsone _database_code_depnum_ccdc_archive 'CCDC 737076' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3-chloro-lawsone oxime' _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 Cl N O3, 0.5(H2 O)' _chemical_formula_sum 'C10 H7 Cl N O3.50' _chemical_formula_weight 232.63 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 Orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 20.874(13) _cell_length_b 20.426(12) _cell_length_c 4.638(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1978(2) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1669 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 18.62 _exptl_crystal_description NEEDLE _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.376 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8312 _exptl_absorpt_correction_T_max 0.9888 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13938 _diffrn_reflns_av_R_equivalents 0.0878 _diffrn_reflns_av_sigmaI/netI 0.0814 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3496 _reflns_number_gt 2773 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0390P)^2^+2.4943P] 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 0.05(14) _refine_ls_number_reflns 3496 _refine_ls_number_parameters 289 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1048 _refine_ls_R_factor_gt 0.0808 _refine_ls_wR_factor_ref 0.1580 _refine_ls_wR_factor_gt 0.1479 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.159 _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 Cl1A Cl 0.79645(7) 0.45580(8) -0.4029(4) 0.0489(5) Uani 1 1 d . . . O1A O 0.7116(3) 0.7000(3) 0.2948(15) 0.0719(17) Uani 1 1 d . . . H1A H 0.7318 0.7341 0.3136 0.108 Uiso 1 1 calc R . . O2A O 0.8120(2) 0.5905(2) -0.2186(12) 0.0541(14) Uani 1 1 d . . . H2A H 0.8149 0.6281 -0.1583 0.081 Uiso 1 1 calc R . . O3A O 0.6858(2) 0.4043(2) -0.0743(13) 0.0590(15) Uani 1 1 d . . . N1A N 0.7446(3) 0.6584(3) 0.1208(15) 0.0559(16) Uani 1 1 d . . . C1A C 0.7248(3) 0.5983(3) 0.1171(16) 0.0351(15) Uani 1 1 d . . . C2A C 0.7639(3) 0.5600(3) -0.0843(14) 0.0380(16) Uani 1 1 d . . . C3A C 0.7510(3) 0.4965(3) -0.1522(14) 0.0343(15) Uani 1 1 d . . . C4A C 0.6978(3) 0.4630(3) -0.0158(16) 0.0435(18) Uani 1 1 d . . . C5A C 0.6074(3) 0.4672(3) 0.3286(17) 0.0462(18) Uani 1 1 d . . . H5A H 0.5992 0.4237 0.2825 0.055 Uiso 1 1 calc R . . C6A C 0.5698(3) 0.4982(4) 0.5259(16) 0.0520(19) Uani 1 1 d . . . H6A H 0.5360 0.4759 0.6116 0.062 Uiso 1 1 calc R . . C7A C 0.5819(3) 0.5632(4) 0.6001(19) 0.0543(19) Uani 1 1 d . . . H7A H 0.5561 0.5846 0.7335 0.065 Uiso 1 1 calc R . . C8A C 0.6321(3) 0.5948(3) 0.4737(15) 0.0428(17) Uani 1 1 d . . . H8A H 0.6408 0.6376 0.5287 0.051 Uiso 1 1 calc R . . C9A C 0.6577(3) 0.4995(3) 0.1953(14) 0.0363(15) Uani 1 1 d . . . C10A C 0.6711(3) 0.5656(3) 0.2657(15) 0.0358(15) Uani 1 1 d . . . O1B O 0.3292(3) 0.1680(3) 0.1796(14) 0.0792(19) Uani 1 1 d . . . H1B H 0.2917 0.1745 0.2248 0.119 Uiso 1 1 calc R . . O2B O 0.4289(2) 0.2930(2) 0.6160(12) 0.0549(13) Uani 1 1 d . . . H2B H 0.3907 0.2848 0.5974 0.082 Uiso 1 1 calc R . . Cl1B Cl 0.56471(8) 0.31632(8) 0.6628(4) 0.0513(5) Uani 1 1 d . . . O3B O 0.6269(2) 0.2205(2) 0.2759(13) 0.0530(13) Uani 1 1 d . . . N1B N 0.3670(3) 0.2096(3) 0.3216(17) 0.065(2) Uani 1 1 d . . . C1B C 0.4291(3) 0.2044(3) 0.2682(15) 0.0393(16) Uani 1 1 d . . . C2B C 0.4629(3) 0.2544(3) 0.4424(16) 0.0392(16) Uani 1 1 d . . . C3B C 0.5281(3) 0.2602(3) 0.4404(15) 0.0374(16) Uani 1 1 d . . . C4B C 0.5675(3) 0.2174(3) 0.2622(16) 0.0386(16) Uani 1 1 d . . . C5B C 0.5716(3) 0.1306(3) -0.1036(15) 0.0436(17) Uani 1 1 d . . . H5B H 0.6157 0.1365 -0.1088 0.052 Uiso 1 1 calc R . . C6B C 0.5430(4) 0.0826(3) -0.2750(16) 0.053(2) Uani 1 1 d . . . H6B H 0.5681 0.0567 -0.3956 0.063 Uiso 1 1 calc R . . C7B C 0.4777(4) 0.0737(3) -0.2650(16) 0.051(2) Uani 1 1 d . . . H7B H 0.4589 0.0408 -0.3748 0.061 Uiso 1 1 calc R . . C8B C 0.4400(4) 0.1130(3) -0.0936(17) 0.051(2) Uani 1 1 d . . . H8B H 0.3958 0.1074 -0.0941 0.061 Uiso 1 1 calc R . . C9B C 0.5347(3) 0.1689(3) 0.0718(14) 0.0343(14) Uani 1 1 d . . . C10B C 0.4676(3) 0.1617(3) 0.0824(16) 0.0404(15) Uani 1 1 d . . . O4 O 0.7746(2) 0.8032(3) 0.0383(17) 0.0682(18) Uani 1 1 d D . . H4A H 0.783(4) 0.8413(19) 0.081(19) 0.11(4) Uiso 1 1 d D . . H4B H 0.793(3) 0.789(3) -0.110(11) 0.07(3) Uiso 1 1 d 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 Cl1A 0.0479(9) 0.0489(10) 0.0499(11) -0.0067(10) -0.0029(10) 0.0158(7) O1A 0.077(4) 0.048(3) 0.091(4) -0.029(3) 0.016(4) -0.014(3) O2A 0.053(3) 0.046(3) 0.063(3) -0.005(3) 0.016(3) -0.008(2) O3A 0.068(3) 0.033(3) 0.076(4) -0.009(3) 0.005(3) 0.000(2) N1A 0.060(3) 0.041(3) 0.067(4) -0.016(4) 0.002(4) 0.015(3) C1A 0.029(3) 0.029(3) 0.047(4) -0.008(3) -0.010(3) 0.002(2) C2A 0.030(3) 0.044(4) 0.039(4) 0.008(3) -0.009(3) -0.001(3) C3A 0.041(3) 0.030(4) 0.032(4) 0.003(3) -0.005(3) 0.004(3) C4A 0.047(4) 0.038(4) 0.045(4) -0.001(3) -0.017(3) 0.004(3) C5A 0.057(4) 0.034(4) 0.047(4) 0.004(4) -0.001(4) 0.003(3) C6A 0.048(4) 0.066(5) 0.042(5) 0.013(4) 0.000(4) -0.007(4) C7A 0.047(4) 0.069(5) 0.048(5) 0.004(5) 0.012(4) 0.024(3) C8A 0.048(4) 0.041(4) 0.039(4) 0.006(3) -0.001(3) 0.016(3) C9A 0.038(3) 0.041(4) 0.030(4) 0.009(3) -0.010(3) 0.001(3) C10A 0.035(3) 0.036(4) 0.037(4) 0.004(3) -0.015(3) 0.005(3) O1B 0.067(3) 0.076(4) 0.095(5) 0.007(4) 0.007(4) -0.004(3) O2B 0.040(2) 0.049(3) 0.076(4) -0.018(3) 0.007(3) 0.003(2) Cl1B 0.0536(10) 0.0421(9) 0.0583(12) -0.0048(9) 0.0010(9) -0.0101(8) O3B 0.031(2) 0.055(3) 0.073(3) -0.009(3) -0.004(3) -0.001(2) N1B 0.051(4) 0.055(4) 0.088(5) 0.024(4) -0.031(4) -0.028(3) C1B 0.045(4) 0.035(4) 0.039(4) 0.007(3) -0.007(3) -0.005(3) C2B 0.040(4) 0.034(4) 0.043(4) 0.004(4) 0.005(3) 0.009(3) C3B 0.043(4) 0.029(4) 0.041(4) 0.005(3) 0.000(3) 0.006(3) C4B 0.033(3) 0.037(4) 0.046(4) 0.007(3) -0.012(3) 0.002(3) C5B 0.039(4) 0.053(5) 0.039(4) 0.000(4) -0.001(3) 0.004(3) C6B 0.066(5) 0.048(4) 0.045(5) -0.003(4) -0.003(4) 0.017(4) C7B 0.069(5) 0.038(4) 0.045(5) -0.006(4) -0.014(4) -0.008(3) C8B 0.054(4) 0.050(5) 0.050(5) 0.002(4) -0.012(4) -0.007(4) C9B 0.041(3) 0.037(4) 0.025(3) 0.007(3) -0.009(3) 0.004(3) C10B 0.043(3) 0.043(4) 0.035(4) 0.012(4) -0.004(4) -0.002(3) O4 0.040(3) 0.046(4) 0.119(6) -0.025(4) 0.003(4) -0.004(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 Cl1A C3A 1.716(7) . ? O1A N1A 1.359(7) . ? O1A H1A 0.8200 . ? O2A C2A 1.336(7) . ? O2A H2A 0.8200 . ? O3A C4A 1.254(8) . ? N1A C1A 1.296(7) . ? C1A C2A 1.467(9) . ? C1A C10A 1.476(9) . ? C2A C3A 1.361(8) . ? C3A C4A 1.451(9) . ? C4A C9A 1.488(9) . ? C5A C6A 1.361(10) . ? C5A C9A 1.385(9) . ? C5A H5A 0.9300 . ? C6A C7A 1.395(10) . ? C6A H6A 0.9300 . ? C7A C8A 1.364(9) . ? C7A H7A 0.9300 . ? C8A C10A 1.395(9) . ? C8A H8A 0.9300 . ? C9A C10A 1.418(8) . ? O1B N1B 1.335(7) . ? O1B H1B 0.8200 . ? O2B C2B 1.332(8) . ? O2B H2B 0.8200 . ? Cl1B C3B 1.722(7) . ? O3B C4B 1.242(7) . ? N1B C1B 1.324(8) . ? C1B C10B 1.467(9) . ? C1B C2B 1.481(9) . ? C2B C3B 1.366(8) . ? C3B C4B 1.457(9) . ? C4B C9B 1.494(9) . ? C5B C9B 1.366(9) . ? C5B C6B 1.396(9) . ? C5B H5B 0.9300 . ? C6B C7B 1.376(10) . ? C6B H6B 0.9300 . ? C7B C8B 1.378(10) . ? C7B H7B 0.9300 . ? C8B C10B 1.410(9) . ? C8B H8B 0.9300 . ? C9B C10B 1.409(8) . ? O4 H4A 0.82(5) . ? O4 H4B 0.84(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 N1A O1A H1A 109.5 . . ? C2A O2A H2A 109.5 . . ? C1A N1A O1A 115.9(6) . . ? N1A C1A C2A 109.6(6) . . ? N1A C1A C10A 131.7(6) . . ? C2A C1A C10A 118.7(5) . . ? O2A C2A C3A 119.0(6) . . ? O2A C2A C1A 117.9(6) . . ? C3A C2A C1A 123.0(6) . . ? C2A C3A C4A 120.1(6) . . ? C2A C3A Cl1A 120.6(5) . . ? C4A C3A Cl1A 119.3(5) . . ? O3A C4A C3A 120.7(7) . . ? O3A C4A C9A 120.6(6) . . ? C3A C4A C9A 118.7(6) . . ? C6A C5A C9A 121.1(7) . . ? C6A C5A H5A 119.5 . . ? C9A C5A H5A 119.5 . . ? C5A C6A C7A 120.3(7) . . ? C5A C6A H6A 119.9 . . ? C7A C6A H6A 119.9 . . ? C8A C7A C6A 118.9(7) . . ? C8A C7A H7A 120.6 . . ? C6A C7A H7A 120.6 . . ? C7A C8A C10A 123.0(7) . . ? C7A C8A H8A 118.5 . . ? C10A C8A H8A 118.5 . . ? C5A C9A C10A 119.9(6) . . ? C5A C9A C4A 118.8(6) . . ? C10A C9A C4A 121.3(6) . . ? C8A C10A C9A 116.8(6) . . ? C8A C10A C1A 125.0(6) . . ? C9A C10A C1A 118.2(6) . . ? N1B O1B H1B 109.5 . . ? C2B O2B H2B 109.5 . . ? C1B N1B O1B 115.8(7) . . ? N1B C1B C10B 134.0(7) . . ? N1B C1B C2B 108.0(6) . . ? C10B C1B C2B 118.0(6) . . ? O2B C2B C3B 118.9(6) . . ? O2B C2B C1B 119.0(5) . . ? C3B C2B C1B 122.0(6) . . ? C2B C3B C4B 121.0(6) . . ? C2B C3B Cl1B 119.7(5) . . ? C4B C3B Cl1B 119.2(5) . . ? O3B C4B C3B 120.3(6) . . ? O3B C4B C9B 121.4(6) . . ? C3B C4B C9B 118.3(5) . . ? C9B C5B C6B 120.1(6) . . ? C9B C5B H5B 120.0 . . ? C6B C5B H5B 120.0 . . ? C7B C6B C5B 119.8(7) . . ? C7B C6B H6B 120.1 . . ? C5B C6B H6B 120.1 . . ? C6B C7B C8B 120.6(7) . . ? C6B C7B H7B 119.7 . . ? C8B C7B H7B 119.7 . . ? C7B C8B C10B 120.8(7) . . ? C7B C8B H8B 119.6 . . ? C10B C8B H8B 119.6 . . ? C5B C9B C10B 121.4(6) . . ? C5B C9B C4B 118.3(6) . . ? C10B C9B C4B 120.3(6) . . ? C9B C10B C8B 117.4(6) . . ? C9B C10B C1B 120.2(6) . . ? C8B C10B C1B 122.4(6) . . ? H4A O4 H4B 115(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 O1A N1A C1A C2A 178.7(6) . . . . ? O1A N1A C1A C10A 1.3(11) . . . . ? N1A C1A C2A O2A 1.7(8) . . . . ? C10A C1A C2A O2A 179.5(6) . . . . ? N1A C1A C2A C3A -174.3(6) . . . . ? C10A C1A C2A C3A 3.5(9) . . . . ? O2A C2A C3A C4A -178.1(6) . . . . ? C1A C2A C3A C4A -2.2(9) . . . . ? O2A C2A C3A Cl1A 0.9(8) . . . . ? C1A C2A C3A Cl1A 176.8(5) . . . . ? C2A C3A C4A O3A -179.3(6) . . . . ? Cl1A C3A C4A O3A 1.7(9) . . . . ? C2A C3A C4A C9A 0.6(9) . . . . ? Cl1A C3A C4A C9A -178.4(5) . . . . ? C9A C5A C6A C7A -0.7(11) . . . . ? C5A C6A C7A C8A -0.6(11) . . . . ? C6A C7A C8A C10A 2.1(11) . . . . ? C6A C5A C9A C10A 0.6(10) . . . . ? C6A C5A C9A C4A 179.2(6) . . . . ? O3A C4A C9A C5A 0.8(9) . . . . ? C3A C4A C9A C5A -179.1(6) . . . . ? O3A C4A C9A C10A 179.4(6) . . . . ? C3A C4A C9A C10A -0.5(8) . . . . ? C7A C8A C10A C9A -2.2(9) . . . . ? C7A C8A C10A C1A 178.2(7) . . . . ? C5A C9A C10A C8A 0.8(9) . . . . ? C4A C9A C10A C8A -177.8(6) . . . . ? C5A C9A C10A C1A -179.6(6) . . . . ? C4A C9A C10A C1A 1.9(8) . . . . ? N1A C1A C10A C8A -6.4(11) . . . . ? C2A C1A C10A C8A 176.4(6) . . . . ? N1A C1A C10A C9A 174.0(7) . . . . ? C2A C1A C10A C9A -3.2(8) . . . . ? O1B N1B C1B C10B -0.2(11) . . . . ? O1B N1B C1B C2B 179.6(6) . . . . ? N1B C1B C2B O2B 1.2(9) . . . . ? C10B C1B C2B O2B -178.9(6) . . . . ? N1B C1B C2B C3B 178.1(6) . . . . ? C10B C1B C2B C3B -2.0(10) . . . . ? O2B C2B C3B C4B 177.7(6) . . . . ? C1B C2B C3B C4B 0.8(10) . . . . ? O2B C2B C3B Cl1B 0.5(9) . . . . ? C1B C2B C3B Cl1B -176.4(5) . . . . ? C2B C3B C4B O3B -175.5(6) . . . . ? Cl1B C3B C4B O3B 1.7(9) . . . . ? C2B C3B C4B C9B 2.5(9) . . . . ? Cl1B C3B C4B C9B 179.8(5) . . . . ? C9B C5B C6B C7B -0.5(11) . . . . ? C5B C6B C7B C8B 2.0(11) . . . . ? C6B C7B C8B C10B -2.2(11) . . . . ? C6B C5B C9B C10B -0.7(10) . . . . ? C6B C5B C9B C4B 177.1(6) . . . . ? O3B C4B C9B C5B -4.5(10) . . . . ? C3B C4B C9B C5B 177.5(6) . . . . ? O3B C4B C9B C10B 173.3(6) . . . . ? C3B C4B C9B C10B -4.7(9) . . . . ? C5B C9B C10B C8B 0.4(9) . . . . ? C4B C9B C10B C8B -177.3(6) . . . . ? C5B C9B C10B C1B -178.7(6) . . . . ? C4B C9B C10B C1B 3.6(9) . . . . ? C7B C8B C10B C9B 1.0(10) . . . . ? C7B C8B C10B C1B -179.9(6) . . . . ? N1B C1B C10B C9B 179.6(7) . . . . ? C2B C1B C10B C9B -0.3(9) . . . . ? N1B C1B C10B C8B 0.5(12) . . . . ? C2B C1B C10B C8B -179.4(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 O4 H4A Cl1A 0.82(5) 2.87(7) 3.464(6) 130(7) 4_655 C8B H8B Cl1A 0.93 2.83 3.607(7) 141.6 3_455 C5B H5B O2A 0.93 2.54 3.125(8) 121.5 4_645 C5A H5A Cl1B 0.93 2.91 3.564(7) 128.9 . O4 H4A O3A 0.82(5) 2.15(6) 2.861(8) 144(9) 4_655 O4 H4B O3B 0.84(6) 2.25(5) 2.926(8) 138(7) 4_654 O1B H1B O4 0.82 2.06 2.794(8) 149.0 2_665 O2B H2B O1A 0.82 2.34 3.051(7) 144.9 2_665 O1A H1A O4 0.82 2.10 2.754(8) 136.5 . O2A H2A O3B 0.82 2.26 2.945(6) 140.7 4_654 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.354 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.067 # Attachment 'Br_lawsone.cif' data_bromo_lawsone _database_code_depnum_ccdc_archive 'CCDC 737077' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3-bromo-lawsone oxime' _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 Br N O3, 0.63(H2 O)' _chemical_formula_sum 'C10 H6 Br N O3.63' _chemical_formula_weight 278.07 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 21.092(6) _cell_length_b 20.588(6) _cell_length_c 4.6388(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2014.3(10) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2866 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 21.76 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.834 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 4.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2088 _exptl_absorpt_correction_T_max 0.7921 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9724 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3437 _reflns_number_gt 2915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0510P)^2^+0.1986P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.017(14) _refine_ls_number_reflns 3437 _refine_ls_number_parameters 290 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.050 _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 Br1A Br 0.56502(3) 0.67757(3) 0.59126(16) 0.0570(2) Uani 1 1 d . . . O1A O 0.3344(3) 0.8354(2) 0.0856(17) 0.0949(17) Uani 1 1 d D . . H1A H 0.2970 0.8279 0.1187 0.142 Uiso 1 1 calc RD . . O2A O 0.42829(17) 0.71107(18) 0.5307(10) 0.0592(12) Uani 1 1 d . . . H2A H 0.3909 0.7213 0.5132 0.089 Uiso 1 1 calc R . . O3A O 0.62579(18) 0.77770(17) 0.2020(11) 0.0565(11) Uani 1 1 d . . . N1A N 0.3695(3) 0.7953(3) 0.2308(15) 0.0771(19) Uani 1 1 d D . . C1A C 0.4327(3) 0.7985(3) 0.1857(13) 0.0436(14) Uani 1 1 d D . . C2A C 0.4642(3) 0.7493(2) 0.3614(12) 0.0408(12) Uani 1 1 d . . . C3A C 0.5266(3) 0.7416(2) 0.3567(12) 0.0403(12) Uani 1 1 d . . . C4A C 0.5686(3) 0.7824(2) 0.1886(13) 0.0406(13) Uani 1 1 d . . . C5A C 0.5751(3) 0.8701(3) -0.1786(13) 0.0505(15) Uani 1 1 d . . . H5A H 0.6187 0.8635 -0.1842 0.061 Uiso 1 1 calc R . . C6A C 0.5478(3) 0.9175(3) -0.3456(14) 0.0606(18) Uani 1 1 d . . . H6A H 0.5733 0.9432 -0.4625 0.073 Uiso 1 1 calc R . . C7A C 0.4837(4) 0.9275(3) -0.3429(14) 0.0635(18) Uani 1 1 d . . . H7A H 0.4660 0.9600 -0.4566 0.076 Uiso 1 1 calc R . . C8A C 0.4445(3) 0.8888(3) -0.1685(14) 0.0546(16) Uani 1 1 d . . . H8A H 0.4009 0.8955 -0.1663 0.065 Uiso 1 1 calc R . . C9A C 0.5372(3) 0.8318(2) -0.0009(12) 0.0396(12) Uani 1 1 d . . . C10A C 0.4712(3) 0.8405(2) -0.0001(13) 0.0436(12) Uani 1 1 d . . . Br1B Br 0.79964(3) 0.53930(3) -0.49696(14) 0.0584(2) Uani 1 1 d . . . O1B O 0.7092(2) 0.2946(2) 0.2121(14) 0.0835(16) Uani 1 1 d D . . H1B H 0.7260 0.2572 0.2032 0.125 Uiso 1 1 d RD . . O2B O 0.80968(19) 0.40264(19) -0.2928(12) 0.0632(12) Uani 1 1 d . . . H2B H 0.8121 0.3652 -0.2330 0.095 Uiso 1 1 calc R . . O3B O 0.6835(2) 0.58604(18) -0.1657(12) 0.0675(14) Uani 1 1 d . . . N1B N 0.7421(2) 0.3359(2) 0.0442(14) 0.0629(15) Uani 1 1 d . . . C1B C 0.7217(2) 0.3951(2) 0.0366(13) 0.0433(13) Uani 1 1 d . . . C2B C 0.7604(3) 0.4326(2) -0.1669(13) 0.0426(13) Uani 1 1 d . . . C3B C 0.7479(3) 0.4946(2) -0.2328(13) 0.0445(14) Uani 1 1 d . . . C4B C 0.6954(3) 0.5288(3) -0.1055(14) 0.0465(14) Uani 1 1 d . . . C5B C 0.6056(3) 0.5259(3) 0.2305(15) 0.0565(16) Uani 1 1 d . . . H5B H 0.5975 0.5688 0.1797 0.068 Uiso 1 1 calc R . . C6B C 0.5671(3) 0.4949(3) 0.4317(16) 0.0650(18) Uani 1 1 d . . . H6B H 0.5332 0.5168 0.5147 0.078 Uiso 1 1 calc R . . C7B C 0.5797(3) 0.4310(3) 0.5077(16) 0.0650(18) Uani 1 1 d . . . H7B H 0.5539 0.4101 0.6409 0.078 Uiso 1 1 calc R . . C8B C 0.6302(3) 0.3985(3) 0.3876(13) 0.0542(15) Uani 1 1 d . . . H8B H 0.6389 0.3561 0.4445 0.065 Uiso 1 1 calc R . . C9B C 0.6561(2) 0.4926(2) 0.1048(13) 0.0438(13) Uani 1 1 d . . . C10B C 0.6685(3) 0.4284(3) 0.1812(12) 0.0430(13) Uani 1 1 d . . . O4 O 0.7738(3) 0.1911(2) 0.9449(19) 0.117(3) Uani 1 1 d U . . O5 O 0.7760(8) 0.2000(7) 0.484(6) 0.087(6) Uani 0.25 1 d PU . . 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 Br1A 0.0605(4) 0.0452(3) 0.0652(4) 0.0052(3) -0.0017(3) 0.0089(2) O1A 0.082(3) 0.086(3) 0.117(5) -0.008(4) -0.008(4) 0.003(3) O2A 0.046(2) 0.058(2) 0.074(3) 0.013(2) 0.006(2) -0.0047(17) O3A 0.037(2) 0.053(2) 0.079(3) 0.003(2) -0.009(2) -0.0025(18) N1A 0.071(4) 0.064(3) 0.096(5) -0.029(3) -0.038(4) 0.030(3) C1A 0.042(3) 0.043(3) 0.046(4) -0.012(3) -0.005(3) 0.000(2) C2A 0.038(3) 0.040(3) 0.044(3) -0.006(2) -0.001(3) -0.003(2) C3A 0.045(3) 0.035(3) 0.042(3) -0.003(2) -0.004(3) -0.002(2) C4A 0.041(3) 0.039(3) 0.042(3) -0.005(2) -0.010(3) -0.006(2) C5A 0.054(4) 0.055(4) 0.043(3) -0.005(3) -0.004(3) -0.005(3) C6A 0.079(5) 0.058(4) 0.045(4) 0.006(3) -0.005(3) -0.016(3) C7A 0.083(5) 0.055(4) 0.052(4) -0.001(3) -0.015(4) 0.006(3) C8A 0.055(4) 0.053(4) 0.056(4) -0.005(3) -0.011(3) 0.003(3) C9A 0.044(3) 0.039(3) 0.036(3) -0.006(3) -0.002(3) -0.004(2) C10A 0.053(3) 0.034(2) 0.044(3) -0.007(3) -0.009(3) -0.002(2) Br1B 0.0559(4) 0.0609(4) 0.0583(4) 0.0061(3) -0.0058(3) -0.0174(3) O1B 0.077(3) 0.064(3) 0.109(4) 0.028(3) 0.013(3) 0.004(2) O2B 0.058(3) 0.047(2) 0.084(3) 0.006(2) 0.017(3) 0.0119(19) O3B 0.080(3) 0.035(2) 0.088(4) 0.011(2) -0.004(3) 0.010(2) N1B 0.057(3) 0.046(3) 0.086(4) 0.011(3) -0.003(3) -0.008(2) C1B 0.041(3) 0.039(3) 0.050(4) 0.006(3) -0.010(3) -0.003(2) C2B 0.040(3) 0.042(3) 0.046(3) -0.003(3) -0.006(3) -0.006(2) C3B 0.048(3) 0.038(3) 0.047(3) -0.004(2) -0.014(3) -0.004(2) C4B 0.054(4) 0.041(3) 0.045(3) -0.003(3) -0.015(3) -0.002(3) C5B 0.056(4) 0.057(4) 0.056(4) -0.013(3) -0.006(3) 0.001(3) C6B 0.055(4) 0.073(4) 0.067(4) -0.027(4) 0.006(4) -0.004(3) C7B 0.057(4) 0.088(5) 0.050(4) -0.018(4) 0.013(4) -0.015(3) C8B 0.057(4) 0.056(4) 0.049(3) -0.004(3) -0.011(3) -0.016(3) C9B 0.043(3) 0.048(3) 0.040(3) -0.013(3) -0.011(3) -0.002(2) C10B 0.041(3) 0.049(3) 0.039(3) -0.003(2) -0.012(3) -0.009(2) O4 0.063(3) 0.064(3) 0.224(8) 0.018(4) 0.000(5) 0.009(2) O5 0.045(9) 0.035(7) 0.181(17) -0.011(11) 0.007(12) 0.015(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 Br1A C3A 1.892(5) . ? O1A N1A 1.298(8) . ? O2A C2A 1.345(6) . ? O3A C4A 1.211(6) . ? N1A C1A 1.350(8) . ? C1A C2A 1.460(8) . ? C1A C10A 1.466(8) . ? C2A C3A 1.325(8) . ? C3A C4A 1.449(8) . ? C4A C9A 1.499(8) . ? C5A C6A 1.373(8) . ? C5A C9A 1.392(8) . ? C6A C7A 1.367(9) . ? C7A C8A 1.404(9) . ? C8A C10A 1.383(8) . ? C9A C10A 1.404(7) . ? Br1B C3B 1.881(6) . ? O1B N1B 1.345(7) . ? O2B C2B 1.342(7) . ? O3B C4B 1.237(6) . ? N1B C1B 1.294(6) . ? C1B C2B 1.468(8) . ? C1B C10B 1.477(8) . ? C2B C3B 1.339(7) . ? C3B C4B 1.438(8) . ? C4B C9B 1.481(8) . ? C5B C6B 1.392(9) . ? C5B C9B 1.396(8) . ? C6B C7B 1.387(9) . ? C7B C8B 1.376(9) . ? C8B C10B 1.395(8) . ? C9B C10B 1.392(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 O1A N1A C1A 116.8(7) . . ? N1A C1A C2A 109.1(5) . . ? N1A C1A C10A 131.8(6) . . ? C2A C1A C10A 119.1(5) . . ? C3A C2A O2A 119.9(5) . . ? C3A C2A C1A 121.7(5) . . ? O2A C2A C1A 118.4(5) . . ? C2A C3A C4A 123.2(5) . . ? C2A C3A Br1A 119.9(4) . . ? C4A C3A Br1A 116.8(4) . . ? O3A C4A C3A 122.4(5) . . ? O3A C4A C9A 121.6(5) . . ? C3A C4A C9A 115.9(5) . . ? C6A C5A C9A 119.7(6) . . ? C7A C6A C5A 121.2(6) . . ? C6A C7A C8A 120.0(6) . . ? C10A C8A C7A 119.6(6) . . ? C5A C9A C10A 119.9(5) . . ? C5A C9A C4A 118.5(5) . . ? C10A C9A C4A 121.6(5) . . ? C8A C10A C9A 119.6(5) . . ? C8A C10A C1A 122.1(5) . . ? C9A C10A C1A 118.4(5) . . ? C1B N1B O1B 116.1(5) . . ? N1B C1B C2B 109.2(5) . . ? N1B C1B C10B 132.7(5) . . ? C2B C1B C10B 118.1(4) . . ? C3B C2B O2B 119.5(5) . . ? C3B C2B C1B 122.6(5) . . ? O2B C2B C1B 117.9(5) . . ? C2B C3B C4B 121.7(5) . . ? C2B C3B Br1B 120.0(4) . . ? C4B C3B Br1B 118.3(4) . . ? O3B C4B C3B 122.1(6) . . ? O3B C4B C9B 120.9(5) . . ? C3B C4B C9B 117.0(5) . . ? C6B C5B C9B 120.0(6) . . ? C7B C6B C5B 119.5(6) . . ? C8B C7B C6B 120.5(6) . . ? C7B C8B C10B 120.7(6) . . ? C10B C9B C5B 120.1(6) . . ? C10B C9B C4B 122.8(5) . . ? C5B C9B C4B 117.1(5) . . ? C9B C10B C8B 119.1(5) . . ? C9B C10B C1B 117.8(5) . . ? C8B C10B C1B 123.1(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 O1A N1A C1A C2A -178.8(5) . . . . ? O1A N1A C1A C10A 0.7(9) . . . . ? N1A C1A C2A C3A 179.5(5) . . . . ? C10A C1A C2A C3A -0.1(8) . . . . ? N1A C1A C2A O2A -0.3(7) . . . . ? C10A C1A C2A O2A -179.9(5) . . . . ? O2A C2A C3A C4A -177.7(5) . . . . ? C1A C2A C3A C4A 2.5(8) . . . . ? O2A C2A C3A Br1A -0.7(7) . . . . ? C1A C2A C3A Br1A 179.5(4) . . . . ? C2A C3A C4A O3A 174.7(5) . . . . ? Br1A C3A C4A O3A -2.3(7) . . . . ? C2A C3A C4A C9A -4.3(8) . . . . ? Br1A C3A C4A C9A 178.6(3) . . . . ? C9A C5A C6A C7A -0.6(9) . . . . ? C5A C6A C7A C8A -0.4(10) . . . . ? C6A C7A C8A C10A 0.0(9) . . . . ? C6A C5A C9A C10A 2.0(8) . . . . ? C6A C5A C9A C4A -177.4(5) . . . . ? O3A C4A C9A C5A 4.2(7) . . . . ? C3A C4A C9A C5A -176.7(5) . . . . ? O3A C4A C9A C10A -175.1(5) . . . . ? C3A C4A C9A C10A 3.9(7) . . . . ? C7A C8A C10A C9A 1.4(9) . . . . ? C7A C8A C10A C1A -179.9(5) . . . . ? C5A C9A C10A C8A -2.4(8) . . . . ? C4A C9A C10A C8A 177.0(5) . . . . ? C5A C9A C10A C1A 178.9(5) . . . . ? C4A C9A C10A C1A -1.8(7) . . . . ? N1A C1A C10A C8A 1.5(9) . . . . ? C2A C1A C10A C8A -179.0(5) . . . . ? N1A C1A C10A C9A -179.7(6) . . . . ? C2A C1A C10A C9A -0.2(7) . . . . ? O1B N1B C1B C2B -177.0(5) . . . . ? O1B N1B C1B C10B 0.9(10) . . . . ? N1B C1B C2B C3B 175.8(5) . . . . ? C10B C1B C2B C3B -2.5(8) . . . . ? N1B C1B C2B O2B -3.3(7) . . . . ? C10B C1B C2B O2B 178.4(5) . . . . ? O2B C2B C3B C4B 179.6(5) . . . . ? C1B C2B C3B C4B 0.5(8) . . . . ? O2B C2B C3B Br1B -0.7(7) . . . . ? C1B C2B C3B Br1B -179.8(4) . . . . ? C2B C3B C4B O3B -179.8(6) . . . . ? Br1B C3B C4B O3B 0.4(8) . . . . ? C2B C3B C4B C9B 0.6(8) . . . . ? Br1B C3B C4B C9B -179.1(4) . . . . ? C9B C5B C6B C7B 0.5(10) . . . . ? C5B C6B C7B C8B 0.6(10) . . . . ? C6B C7B C8B C10B -1.9(9) . . . . ? C6B C5B C9B C10B -0.3(9) . . . . ? C6B C5B C9B C4B -179.4(5) . . . . ? O3B C4B C9B C10B -179.2(5) . . . . ? C3B C4B C9B C10B 0.4(8) . . . . ? O3B C4B C9B C5B -0.1(8) . . . . ? C3B C4B C9B C5B 179.5(5) . . . . ? C5B C9B C10B C8B -1.0(8) . . . . ? C4B C9B C10B C8B 178.1(5) . . . . ? C5B C9B C10B C1B 178.6(5) . . . . ? C4B C9B C10B C1B -2.3(7) . . . . ? C7B C8B C10B C9B 2.1(8) . . . . ? C7B C8B C10B C1B -177.5(6) . . . . ? N1B C1B C10B C9B -174.5(6) . . . . ? C2B C1B C10B C9B 3.3(7) . . . . ? N1B C1B C10B C8B 5.1(10) . . . . ? C2B C1B C10B C8B -177.2(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 O1B H1B O5 0.85 2.05 2.71(2) 134.9 . O1B H1B O4 0.85 2.07 2.818(8) 145.7 1_554 O1A H1A O5 0.82 1.76 2.487(19) 147.0 2_664 O1A H1A O4 0.82 2.16 2.879(9) 146.2 2_664 O2B H2B O3A 0.82 2.25 2.910(5) 138.1 4_644 O2A H2A O1B 0.82 2.33 3.021(6) 142.8 2_665 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.614 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.082 # Attachment 'I_lawsone.cif' data_ilow _database_code_depnum_ccdc_archive 'CCDC 737078' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3-iodo-lawsone oxime' _chemical_melting_point ? _chemical_formula_moiety 'C10 H6 I N O3, 2 (H2 O)' _chemical_formula_sum 'C10 H10 I N O5' _chemical_formula_weight 351.09 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' 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' N N 0.0061 0.0033 '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 15.892(3) _cell_length_b 4.5575(9) _cell_length_c 18.335(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.667(3) _cell_angle_gamma 90.00 _cell_volume 1242.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3684 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 28.06 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.877 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 2.586 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4734 _exptl_absorpt_correction_T_max 0.8603 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5759 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2180 _reflns_number_gt 2008 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0368P)^2^+0.4898P] 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 2180 _refine_ls_number_parameters 178 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0660 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.003 _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 1.154750(13) 0.16291(5) 0.247942(12) 0.05185(11) Uani 1 1 d . . . O1 O 0.81682(16) 1.0809(6) 0.12037(13) 0.0559(6) Uani 1 1 d D . . O2 O 0.99859(15) 0.5032(6) 0.11921(12) 0.0524(5) Uani 1 1 d D . . O3 O 1.10113(18) 0.3785(6) 0.38927(14) 0.0710(7) Uani 1 1 d . . . N1 N 0.88129(17) 0.8752(5) 0.12489(14) 0.0447(6) Uani 1 1 d . . . C1 C 0.92252(19) 0.7621(7) 0.19300(16) 0.0388(6) Uani 1 1 d . . . C2 C 0.99207(18) 0.5536(6) 0.18873(16) 0.0397(6) Uani 1 1 d . . . C3 C 1.05001(18) 0.4273(6) 0.25341(17) 0.0410(6) Uani 1 1 d . . . C4 C 1.0468(2) 0.4846(7) 0.32991(17) 0.0479(7) Uani 1 1 d . . . C5 C 0.9662(2) 0.7211(8) 0.40716(19) 0.0567(8) Uani 1 1 d . . . H5 H 1.0073 0.6315 0.4508 0.068 Uiso 1 1 calc R . . C6 C 0.8996(3) 0.8927(8) 0.41558(19) 0.0609(9) Uani 1 1 d . . . H6 H 0.8944 0.9148 0.4643 0.073 Uiso 1 1 calc R . . C7 C 0.8403(2) 1.0323(9) 0.35152(19) 0.0578(8) Uani 1 1 d . . . H7 H 0.7956 1.1520 0.3573 0.069 Uiso 1 1 calc R . . C8 C 0.8463(2) 0.9965(8) 0.27848(18) 0.0490(7) Uani 1 1 d . . . H8 H 0.8059 1.0928 0.2357 0.059 Uiso 1 1 calc R . . C9 C 0.9737(2) 0.6781(6) 0.33465(17) 0.0436(7) Uani 1 1 d . . . C10 C 0.9126(2) 0.8169(6) 0.26878(16) 0.0399(6) Uani 1 1 d . . . H1A H 0.802(3) 1.138(8) 0.0757(13) 0.078(14) Uiso 1 1 d D . . H2A H 0.962(2) 0.595(7) 0.0865(17) 0.059(11) Uiso 1 1 d D . . O4 O 0.3874(2) 0.8178(7) 0.46916(16) 0.0697(7) Uani 1 1 d D . . H4A H 0.416(3) 0.828(9) 0.440(3) 0.101(19) Uiso 1 1 d D . . H4B H 0.364(3) 0.655(6) 0.467(3) 0.087(17) Uiso 1 1 d D . . O5 O 0.7166(2) 0.6984(7) 0.52869(15) 0.0663(7) Uani 1 1 d D . . H5A H 0.693(3) 0.853(6) 0.532(3) 0.079(15) Uiso 1 1 d D . . H5B H 0.7678(15) 0.675(8) 0.556(2) 0.073(14) Uiso 1 1 d 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 0.04179(15) 0.04734(16) 0.06404(17) 0.00303(9) 0.01571(11) 0.00153(8) O1 0.0564(14) 0.0655(14) 0.0453(12) 0.0120(11) 0.0171(10) 0.0178(12) O2 0.0507(13) 0.0666(16) 0.0397(11) 0.0013(11) 0.0159(10) 0.0098(12) O3 0.0617(15) 0.098(2) 0.0440(13) 0.0193(13) 0.0075(11) 0.0221(14) N1 0.0425(14) 0.0461(14) 0.0427(13) 0.0048(11) 0.0116(11) 0.0027(11) C1 0.0375(14) 0.0406(14) 0.0376(15) -0.0027(12) 0.0126(12) -0.0076(12) C2 0.0358(14) 0.0411(15) 0.0407(15) -0.0024(12) 0.0117(11) -0.0066(12) C3 0.0352(14) 0.0402(14) 0.0476(16) 0.0030(13) 0.0147(12) -0.0020(12) C4 0.0415(15) 0.0518(18) 0.0447(16) 0.0072(14) 0.0081(13) -0.0048(14) C5 0.061(2) 0.070(2) 0.0371(16) 0.0024(15) 0.0139(15) -0.0073(17) C6 0.070(2) 0.076(2) 0.0400(17) -0.0098(16) 0.0240(16) -0.0105(19) C7 0.0574(19) 0.066(2) 0.0547(19) -0.0057(17) 0.0261(16) -0.0018(18) C8 0.0463(17) 0.0564(19) 0.0438(15) -0.0028(15) 0.0152(13) -0.0009(15) C9 0.0433(16) 0.0470(17) 0.0385(15) 0.0011(12) 0.0121(12) -0.0093(13) C10 0.0398(15) 0.0413(16) 0.0365(14) -0.0017(12) 0.0110(12) -0.0100(12) O4 0.0797(19) 0.081(2) 0.0554(15) -0.0018(13) 0.0323(14) -0.0113(15) O5 0.0590(17) 0.078(2) 0.0480(14) -0.0145(13) 0.0017(12) 0.0025(14) _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 I1 C3 2.086(3) . ? O1 N1 1.369(3) . ? O1 H1A 0.810(19) . ? O2 C2 1.335(3) . ? O2 H2A 0.792(18) . ? O3 C4 1.225(4) . ? N1 C1 1.295(4) . ? C1 C10 1.474(4) . ? C1 C2 1.480(4) . ? C2 C3 1.347(4) . ? C3 C4 1.445(4) . ? C4 C9 1.486(4) . ? C5 C6 1.369(5) . ? C5 C9 1.389(4) . ? C5 H5 0.9300 . ? C6 C7 1.375(5) . ? C6 H6 0.9300 . ? C7 C8 1.386(4) . ? C7 H7 0.9300 . ? C8 C10 1.394(4) . ? C8 H8 0.9300 . ? C9 C10 1.405(4) . ? O4 H4A 0.82(5) . ? O4 H4B 0.824(19) . ? O5 H5A 0.810(18) . ? O5 H5B 0.800(19) . ? 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 N1 O1 H1A 103(3) . . ? C2 O2 H2A 110(3) . . ? C1 N1 O1 116.4(2) . . ? N1 C1 C10 131.0(3) . . ? N1 C1 C2 109.7(2) . . ? C10 C1 C2 119.3(3) . . ? O2 C2 C3 120.5(3) . . ? O2 C2 C1 118.2(2) . . ? C3 C2 C1 121.3(3) . . ? C2 C3 C4 122.0(3) . . ? C2 C3 I1 120.9(2) . . ? C4 C3 I1 116.9(2) . . ? O3 C4 C3 122.4(3) . . ? O3 C4 C9 120.2(3) . . ? C3 C4 C9 117.4(2) . . ? C6 C5 C9 121.3(3) . . ? C6 C5 H5 119.4 . . ? C9 C5 H5 119.4 . . ? C5 C6 C7 119.5(3) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C6 C7 C8 120.7(3) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C7 C8 C10 120.4(3) . . ? C7 C8 H8 119.8 . . ? C10 C8 H8 119.8 . . ? C5 C9 C10 119.5(3) . . ? C5 C9 C4 118.2(3) . . ? C10 C9 C4 122.3(3) . . ? C8 C10 C9 118.6(3) . . ? C8 C10 C1 123.8(3) . . ? C9 C10 C1 117.6(3) . . ? H4A O4 H4B 112(4) . . ? H5A O5 H5B 118(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 O1 N1 C1 C10 -0.3(4) . . . . ? O1 N1 C1 C2 -177.9(2) . . . . ? N1 C1 C2 O2 -3.4(4) . . . . ? C10 C1 C2 O2 178.7(2) . . . . ? N1 C1 C2 C3 173.7(3) . . . . ? C10 C1 C2 C3 -4.2(4) . . . . ? O2 C2 C3 C4 177.9(3) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? O2 C2 C3 I1 2.5(4) . . . . ? C1 C2 C3 I1 -174.6(2) . . . . ? C2 C3 C4 O3 -177.5(3) . . . . ? I1 C3 C4 O3 -1.9(4) . . . . ? C2 C3 C4 C9 3.1(4) . . . . ? I1 C3 C4 C9 178.7(2) . . . . ? C9 C5 C6 C7 -1.9(6) . . . . ? C5 C6 C7 C8 1.2(6) . . . . ? C6 C7 C8 C10 0.3(5) . . . . ? C6 C5 C9 C10 1.1(5) . . . . ? C6 C5 C9 C4 -179.0(3) . . . . ? O3 C4 C9 C5 -3.3(5) . . . . ? C3 C4 C9 C5 176.1(3) . . . . ? O3 C4 C9 C10 176.7(3) . . . . ? C3 C4 C9 C10 -3.9(4) . . . . ? C7 C8 C10 C9 -1.1(4) . . . . ? C7 C8 C10 C1 178.7(3) . . . . ? C5 C9 C10 C8 0.4(4) . . . . ? C4 C9 C10 C8 -179.6(3) . . . . ? C5 C9 C10 C1 -179.3(3) . . . . ? C4 C9 C10 C1 0.7(4) . . . . ? N1 C1 C10 C8 6.2(5) . . . . ? C2 C1 C10 C8 -176.4(3) . . . . ? N1 C1 C10 C9 -174.1(3) . . . . ? C2 C1 C10 C9 3.3(4) . . . . ? 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 O5 H5B O3 0.800(19) 1.98(2) 2.775(4) 172(4) 3_766 O5 H5A O4 0.810(18) 1.97(2) 2.764(4) 169(4) 3_676 O4 H4B O5 0.824(19) 2.08(2) 2.883(4) 166(4) 3_666 O4 H4A O2 0.82(5) 2.17(5) 2.949(4) 160(4) 2_655 O1 H1A O5 0.810(19) 1.85(2) 2.648(3) 167(4) 2_655 O2 H2A O4 0.792(18) 2.10(2) 2.815(4) 151(4) 4_675 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.556 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.074