# 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_platon _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-nitrobenzamide:1,4-diiodobenzene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 I N2 O3' _chemical_formula_weight 331.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' I I -0.4740 1.8120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 '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 6.523(2) _cell_length_b 8.265(3) _cell_length_c 10.224(4) _cell_angle_alpha 76.259(7) _cell_angle_beta 87.845(7) _cell_angle_gamma 87.161(7) _cell_volume 534.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5100 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.056 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 2.988 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.5864 _exptl_absorpt_correction_T_max 0.7543 #=============================================================================== # 7. EXPERIMENTAL DATA _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5359 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0630 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2428 _reflns_number_gt 2249 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.1701P)^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_number_reflns 2428 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.2195 _refine_ls_wR_factor_gt 0.2156 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 O2 O -0.2022(13) 0.3352(10) 1.1009(9) 0.0369(18) Uani 1 1 d . . . N2 N 0.2180(10) 0.0016(9) 0.5463(8) 0.0205(14) Uani 1 1 d . . . H2A H 0.3006 -0.0267 0.4847 0.025 Uiso 1 1 calc R . . H2B H 0.0869 -0.0200 0.5493 0.025 Uiso 1 1 calc R . . O3 O -0.4345(11) 0.1918(11) 1.0425(8) 0.0410(19) Uani 1 1 d . . . O1 O 0.4769(11) 0.1095(11) 0.6336(8) 0.0348(18) Uani 1 1 d . . . N1 N -0.2632(11) 0.2470(8) 1.0303(7) 0.0216(13) Uani 1 1 d . . . C5 C -0.0468(10) 0.0485(9) 0.7647(7) 0.0171(13) Uani 1 1 d . . . H5 H -0.0837 -0.0299 0.7161 0.021 Uiso 1 1 calc R . . C6 C -0.1802(13) 0.0885(10) 0.8610(8) 0.0206(15) Uani 1 1 d . . . H6 H -0.3091 0.0380 0.8800 0.025 Uiso 1 1 calc R . . C7 C -0.1224(12) 0.2037(10) 0.9292(8) 0.0185(15) Uani 1 1 d . . . C1 C 0.0660(14) 0.2793(10) 0.9067(9) 0.0246(17) Uani 1 1 d . . . H24 H 0.0945 0.3786 0.9360 0.029 Uiso 1 1 d R . . C2 C 0.1982(12) 0.2375(9) 0.8088(7) 0.0207(14) Uani 1 1 d . . . H2 H 0.3277 0.2868 0.7892 0.025 Uiso 1 1 calc R . . C4 C 0.2886(13) 0.0741(8) 0.6317(8) 0.0243(18) Uani 1 1 d . . . C3 C 0.1367(9) 0.1207(6) 0.7391(5) 0.0068(12) Uiso 1 1 d . . . I1 I 0.34608(7) 0.38324(5) 0.26850(4) 0.0229(3) Uani 1 1 d . . . C10 C 0.1964(12) 0.5590(10) 0.4864(8) 0.0225(16) Uani 1 1 d . . . H10 H 0.3313 0.5993 0.4767 0.027 Uiso 1 1 calc R . . C8 C -0.0593(13) 0.3965(10) 0.4189(9) 0.0233(16) Uani 1 1 d . . . H8 H -0.1004 0.3264 0.3641 0.028 Uiso 1 1 calc R . . C9 C 0.1368(14) 0.4553(10) 0.4053(9) 0.0217(16) 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 O2 0.038(4) 0.042(4) 0.039(4) -0.027(3) 0.011(3) -0.007(3) N2 0.010(3) 0.030(4) 0.027(4) -0.017(3) 0.002(2) -0.004(3) O3 0.022(3) 0.067(5) 0.041(4) -0.026(4) 0.012(3) -0.007(3) O1 0.015(3) 0.055(5) 0.041(4) -0.023(4) 0.004(3) -0.011(3) N1 0.025(3) 0.024(3) 0.015(3) -0.005(2) 0.005(2) 0.006(3) C5 0.011(3) 0.025(3) 0.019(3) -0.010(3) 0.005(2) -0.006(3) C6 0.019(4) 0.023(4) 0.020(4) -0.007(3) 0.000(3) -0.001(3) C7 0.017(4) 0.027(4) 0.012(3) -0.007(3) 0.007(3) 0.004(3) C1 0.027(4) 0.025(4) 0.025(4) -0.012(3) -0.001(3) -0.002(3) C2 0.021(4) 0.020(3) 0.024(4) -0.009(3) 0.003(3) -0.006(3) C4 0.030(4) 0.012(3) 0.028(4) 0.005(3) -0.019(3) -0.007(3) I1 0.0225(4) 0.0247(4) 0.0212(4) -0.0060(2) 0.0050(2) 0.0021(2) C10 0.016(4) 0.029(4) 0.025(4) -0.011(3) 0.004(3) -0.003(3) C8 0.022(4) 0.025(4) 0.026(4) -0.014(3) 0.005(3) -0.004(3) C9 0.025(4) 0.018(3) 0.020(4) -0.001(3) 0.000(3) 0.000(3) _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 O2 N1 1.229(11) . ? N2 C4 1.280(10) . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? O3 N1 1.219(11) . ? O1 C4 1.279(11) . ? N1 C7 1.453(9) . ? C5 C3 1.353(8) . ? C5 C6 1.378(11) . ? C5 H5 0.9500 . ? C6 C7 1.381(11) . ? C6 H6 0.9500 . ? C7 C1 1.393(12) . ? C1 C2 1.391(12) . ? C1 H24 0.9668 . ? C2 C3 1.409(8) . ? C2 H2 0.9500 . ? C4 C3 1.555(11) . ? I1 C9 2.085(9) . ? C10 C8 1.394(11) 2_566 ? C10 C9 1.403(12) . ? C10 H10 0.9500 . ? C8 C9 1.381(12) . ? C8 C10 1.394(11) 2_566 ? C8 H8 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N2 H2A 120.0 . . ? C4 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? O3 N1 O2 123.3(7) . . ? O3 N1 C7 118.4(7) . . ? O2 N1 C7 118.3(7) . . ? C3 C5 C6 120.2(7) . . ? C3 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 118.5(7) . . ? C5 C6 H6 120.8 . . ? C7 C6 H6 120.8 . . ? C6 C7 C1 123.0(8) . . ? C6 C7 N1 118.7(7) . . ? C1 C7 N1 118.4(7) . . ? C2 C1 C7 117.6(7) . . ? C2 C1 H24 116.9 . . ? C7 C1 H24 123.3 . . ? C1 C2 C3 118.8(7) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? O1 C4 N2 123.6(9) . . ? O1 C4 C3 118.3(7) . . ? N2 C4 C3 118.0(7) . . ? C5 C3 C2 121.9(6) . . ? C5 C3 C4 120.2(5) . . ? C2 C3 C4 117.9(6) . . ? C8 C10 C9 120.6(8) 2_566 . ? C8 C10 H10 119.7 2_566 . ? C9 C10 H10 119.7 . . ? C9 C8 C10 119.4(8) . 2_566 ? C9 C8 H8 120.3 . . ? C10 C8 H8 120.3 2_566 . ? C8 C9 C10 120.0(8) . . ? C8 C9 I1 119.7(6) . . ? C10 C9 I1 120.3(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C5 C6 C7 0.4(12) . . . . ? C5 C6 C7 C1 -1.1(13) . . . . ? C5 C6 C7 N1 179.6(7) . . . . ? O3 N1 C7 C6 -6.6(12) . . . . ? O2 N1 C7 C6 172.1(8) . . . . ? O3 N1 C7 C1 174.1(9) . . . . ? O2 N1 C7 C1 -7.2(12) . . . . ? C6 C7 C1 C2 1.2(13) . . . . ? N1 C7 C1 C2 -179.5(7) . . . . ? C7 C1 C2 C3 -0.7(12) . . . . ? C6 C5 C3 C2 0.1(11) . . . . ? C6 C5 C3 C4 179.3(6) . . . . ? C1 C2 C3 C5 0.1(11) . . . . ? C1 C2 C3 C4 -179.1(7) . . . . ? O1 C4 C3 C5 -162.3(7) . . . . ? N2 C4 C3 C5 17.4(9) . . . . ? O1 C4 C3 C2 16.9(10) . . . . ? N2 C4 C3 C2 -163.4(7) . . . . ? C10 C8 C9 C10 -0.1(14) 2_566 . . . ? C10 C8 C9 I1 178.0(6) 2_566 . . . ? C8 C10 C9 C8 0.1(15) 2_566 . . . ? C8 C10 C9 I1 -178.0(6) 2_566 . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 8.367 _refine_diff_density_min -2.261 _refine_diff_density_rms 0.506 _database_code_depnum_ccdc_archive 'CCDC 940324' ####################################################################### # # 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_platon _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-iodobenzamide: 1,4-dinitrobenzene' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 I N O4' _chemical_formula_weight 335.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 9.1722(9) _cell_length_b 9.8317(10) _cell_length_c 11.7873(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.719(6) _cell_angle_gamma 90.00 _cell_volume 1062.88(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8809 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.094 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 3.011 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.5842 _exptl_absorpt_correction_T_max 0.7528 #=============================================================================== # 7. EXPERIMENTAL DATA _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5588 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1287 _reflns_number_gt 1267 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0208P)^2^+2.5231P] 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 1287 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0166 _refine_ls_R_factor_gt 0.0162 _refine_ls_wR_factor_ref 0.0502 _refine_ls_wR_factor_gt 0.0499 _refine_ls_goodness_of_fit_ref 1.209 _refine_ls_restrained_S_all 1.209 _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 C1 C -0.2823(3) 0.5000 0.9395(3) 0.0171(6) Uani 1 2 d S . . C2 C -0.1362(3) 0.5000 0.8828(3) 0.0167(6) Uani 1 2 d S . . C3 C -0.0680(3) 0.3786(2) 0.8550(2) 0.0235(5) Uani 1 1 d . . . H3 H -0.1151 0.2948 0.8708 0.028 Uiso 1 1 calc R . . C4 C 0.0679(3) 0.3778(2) 0.8046(2) 0.0230(5) Uani 1 1 d . . . H4 H 0.1137 0.2941 0.7862 0.028 Uiso 1 1 calc R . . C5 C 0.1361(3) 0.5000 0.7813(2) 0.0174(6) Uani 1 2 d S . . I1 I 0.34765(2) 0.5000 0.715276(17) 0.02226(8) Uani 1 2 d S . . N1 O -0.3426(2) 0.3864(2) 0.9619(2) 0.0409(5) Uani 0.50 1 d P . . O1 O -0.3426(2) 0.3864(2) 0.9619(2) 0.0409(5) Uani 0.50 1 d P . . H1N H -0.4321 0.3936 1.0109 0.049 Uiso 1 1 d . . . H2N H -0.2840 0.2988 0.9824 0.049 Uiso 1 1 d . . . C6 C 0.1301(3) 0.5000 0.4482(3) 0.0187(6) Uani 1 2 d S . . C7 C 0.0663(3) 0.6233(2) 0.4732(2) 0.0240(5) Uani 1 1 d . . . H7 H 0.1128 0.7064 0.4538 0.029 Uiso 1 1 calc R . . N2 N 0.2739(3) 0.5000 0.3946(2) 0.0250(6) Uani 1 2 d S . . O2 O 0.3309(2) 0.3903(2) 0.37417(19) 0.0402(5) 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 C1 0.0174(14) 0.0188(14) 0.0152(13) 0.000 -0.0005(11) 0.000 C2 0.0140(14) 0.0192(14) 0.0168(13) 0.000 0.0012(11) 0.000 C3 0.0208(11) 0.0167(10) 0.0331(12) -0.0013(9) 0.0081(9) -0.0023(8) C4 0.0218(11) 0.0180(10) 0.0294(12) -0.0019(9) 0.0067(9) 0.0017(9) C5 0.0132(14) 0.0224(15) 0.0165(14) 0.000 0.0011(11) 0.000 I1 0.01483(12) 0.03027(13) 0.02179(12) 0.000 0.00446(8) 0.000 N1 0.0239(10) 0.0245(10) 0.0748(15) 0.0004(10) 0.0170(10) -0.0012(8) O1 0.0239(10) 0.0245(10) 0.0748(15) 0.0004(10) 0.0170(10) -0.0012(8) C6 0.0143(14) 0.0246(15) 0.0173(14) 0.000 0.0009(11) 0.000 C7 0.0220(11) 0.0192(11) 0.0310(12) 0.0025(9) 0.0026(9) -0.0025(9) N2 0.0198(14) 0.0330(16) 0.0222(13) 0.000 0.0029(11) 0.000 O2 0.0272(10) 0.0392(11) 0.0548(13) -0.0043(10) 0.0172(9) 0.0073(9) _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 C1 O1 1.275(2) 6_565 ? C1 N1 1.275(2) 6_565 ? C1 N1 1.275(2) . ? C1 C2 1.505(4) . ? C2 C3 1.388(3) . ? C2 C3 1.388(3) 6_565 ? C3 C4 1.387(3) . ? C4 C5 1.384(3) . ? C5 C4 1.384(3) 6_565 ? C5 I1 2.100(3) . ? C6 C7 1.379(3) 6_565 ? C6 C7 1.379(3) . ? C6 N2 1.470(4) . ? C7 C7 1.379(5) 2_556 ? N2 O2 1.224(2) 6_565 ? N2 O2 1.224(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 0.0(2) 6_565 6_565 ? O1 C1 N1 122.3(3) 6_565 . ? N1 C1 N1 122.3(3) 6_565 . ? O1 C1 C2 118.85(15) 6_565 . ? N1 C1 C2 118.85(15) 6_565 . ? N1 C1 C2 118.85(15) . . ? C3 C2 C3 118.5(3) . 6_565 ? C3 C2 C1 120.74(14) . . ? C3 C2 C1 120.74(14) 6_565 . ? C4 C3 C2 121.1(2) . . ? C5 C4 C3 119.4(2) . . ? C4 C5 C4 120.5(3) . 6_565 ? C4 C5 I1 119.71(14) . . ? C4 C5 I1 119.71(14) 6_565 . ? C7 C6 C7 123.1(3) 6_565 . ? C7 C6 N2 118.47(15) 6_565 . ? C7 C6 N2 118.47(15) . . ? C7 C7 C6 118.47(15) 2_556 . ? O2 N2 O2 123.6(3) 6_565 . ? O2 N2 C6 118.19(15) 6_565 . ? O2 N2 C6 118.19(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -178.8(3) 6_565 . . . ? N1 C1 C2 C3 -178.8(3) 6_565 . . . ? N1 C1 C2 C3 0.1(4) . . . . ? O1 C1 C2 C3 -0.1(4) 6_565 . . 6_565 ? N1 C1 C2 C3 -0.1(4) 6_565 . . 6_565 ? N1 C1 C2 C3 178.8(3) . . . 6_565 ? C3 C2 C3 C4 2.5(5) 6_565 . . . ? C1 C2 C3 C4 -178.8(3) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C3 C4 C5 C4 -2.1(5) . . . 6_565 ? C3 C4 C5 I1 175.86(19) . . . . ? C7 C6 C7 C7 0.9(6) 6_565 . . 2_556 ? N2 C6 C7 C7 -177.9(3) . . . 2_556 ? C7 C6 N2 O2 -178.9(3) 6_565 . . 6_565 ? C7 C6 N2 O2 -0.1(4) . . . 6_565 ? C7 C6 N2 O2 0.1(4) 6_565 . . . ? C7 C6 N2 O2 178.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.504 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 940325' ####################################################################### # # 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_datam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-nitrobenzamide:oxalic acid:1,4-diiodobenzene' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H9 I N2 O5' _chemical_formula_weight 376.10 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.6257(12) _cell_length_b 9.9114(9) _cell_length_c 9.5779(8) _cell_angle_alpha 90.00 _cell_angle_beta 106.893(7) _cell_angle_gamma 90.00 _cell_volume 1237.68(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12702 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.018 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 2.606 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.5086 _exptl_absorpt_correction_T_max 0.6237 #=============================================================================== # 7. EXPERIMENTAL DATA _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12749 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2836 _reflns_number_gt 2749 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0231P)^2^+0.9967P] 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 2836 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0213 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0548 _refine_ls_wR_factor_gt 0.0543 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.165 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H2 H 0.7113(16) 0.686(2) 0.216(2) 0.012(5) Uiso 1 1 d . . . H4 H 0.8652(18) 0.318(2) 0.062(3) 0.022(6) Uiso 1 1 d . . . H1 H 0.7804(17) 0.707(2) 0.029(2) 0.015(5) Uiso 1 1 d . . . H5 H 0.5031(19) 0.801(3) 0.384(3) 0.026(6) Uiso 1 1 d . . . H3 H 0.7972(19) 0.300(3) 0.257(3) 0.026(6) Uiso 1 1 d . . . H6 H 0.5645(19) 1.193(3) 0.421(3) 0.026(6) Uiso 1 1 d . . . H9 H 0.9064(18) 0.717(3) -0.078(3) 0.020(6) Uiso 1 1 d . . . H8 H 0.9248(19) 0.660(3) -0.209(3) 0.026(6) Uiso 1 1 d . . . H7 H 0.942(2) 0.426(4) -0.285(4) 0.059(10) Uiso 1 1 d . . . I1 I 0.599142(10) 0.988921(14) 0.203848(14) 0.02309(6) Uani 1 1 d . . . C1 C 0.54019(17) 0.9955(2) 0.3832(2) 0.0192(4) Uani 1 1 d . . . C2 C 0.50252(17) 0.8788(2) 0.4285(2) 0.0221(4) Uani 1 1 d . . . C3 C 0.53773(16) 1.1170(2) 0.4540(2) 0.0213(4) Uani 1 1 d . . . O2 O 0.67453(13) 0.58221(17) 0.42139(18) 0.0291(4) Uani 1 1 d . . . O1 O 0.88795(11) 0.42217(14) -0.16614(15) 0.0188(3) Uani 1 1 d . . . O5 O 0.97680(11) 0.40650(13) -0.35820(15) 0.0189(3) Uani 1 1 d . . . O3 O 0.70926(16) 0.36947(18) 0.4359(2) 0.0391(4) Uani 1 1 d . . . N1 N 0.90594(13) 0.64759(17) -0.13161(19) 0.0172(3) Uani 1 1 d . . . O4 O 0.93453(12) 0.61982(14) -0.42737(16) 0.0228(3) Uani 1 1 d . . . C8 C 0.83323(15) 0.51663(17) 0.0267(2) 0.0130(4) Uani 1 1 d . . . C12 C 0.97378(16) 0.51144(17) -0.4395(2) 0.0138(4) Uani 1 1 d . . . N2 N 0.70830(14) 0.48022(17) 0.3793(2) 0.0197(4) Uani 1 1 d . . . C10 C 0.74416(14) 0.61534(19) 0.1852(2) 0.0150(4) Uani 1 1 d . . . C11 C 0.87802(15) 0.52710(18) -0.0977(2) 0.0136(3) Uani 1 1 d . . . C9 C 0.78616(14) 0.62727(19) 0.0708(2) 0.0149(3) Uani 1 1 d . . . C5 C 0.75038(16) 0.49159(18) 0.2550(2) 0.0149(4) Uani 1 1 d . . . C6 C 0.79453(15) 0.37875(19) 0.2119(2) 0.0179(4) Uani 1 1 d . . . C7 C 0.83571(15) 0.39208(19) 0.0962(2) 0.0159(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 I1 0.01959(9) 0.03562(10) 0.01552(9) 0.00358(5) 0.00740(6) 0.00538(5) C1 0.0152(10) 0.0278(10) 0.0147(10) 0.0022(7) 0.0044(8) 0.0019(7) C2 0.0244(10) 0.0214(10) 0.0206(10) -0.0031(8) 0.0069(8) 0.0003(8) C3 0.0212(10) 0.0215(10) 0.0219(10) 0.0024(8) 0.0076(8) -0.0025(8) O2 0.0368(9) 0.0296(8) 0.0303(8) -0.0072(7) 0.0243(7) -0.0035(7) O1 0.0270(7) 0.0146(6) 0.0198(7) -0.0017(5) 0.0146(6) -0.0002(5) O5 0.0288(8) 0.0147(6) 0.0187(7) 0.0022(5) 0.0154(6) 0.0028(6) O3 0.0575(12) 0.0329(9) 0.0407(10) 0.0144(8) 0.0362(9) 0.0064(8) N1 0.0238(9) 0.0150(8) 0.0168(8) -0.0017(6) 0.0122(7) -0.0028(6) O4 0.0349(8) 0.0190(7) 0.0211(7) 0.0056(5) 0.0185(6) 0.0113(6) C8 0.0113(9) 0.0159(8) 0.0126(9) -0.0013(6) 0.0050(7) -0.0014(6) C12 0.0151(9) 0.0144(8) 0.0126(9) -0.0004(6) 0.0049(7) -0.0003(6) N2 0.0176(9) 0.0258(9) 0.0187(9) 0.0009(7) 0.0101(7) -0.0030(7) C10 0.0139(8) 0.0152(8) 0.0172(9) -0.0018(7) 0.0066(7) 0.0006(7) C11 0.0125(8) 0.0169(8) 0.0118(9) 0.0005(6) 0.0042(7) 0.0008(7) C9 0.0147(8) 0.0142(8) 0.0166(9) 0.0005(7) 0.0055(7) 0.0011(7) C5 0.0136(9) 0.0199(9) 0.0128(9) -0.0007(6) 0.0063(7) -0.0024(7) C6 0.0190(9) 0.0158(9) 0.0201(10) 0.0042(7) 0.0077(8) 0.0003(7) C7 0.0190(9) 0.0148(8) 0.0157(8) 0.0000(7) 0.0080(7) 0.0016(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 I1 C1 2.098(2) . ? C1 C2 1.385(3) . ? C1 C3 1.387(3) . ? C2 C3 1.388(3) 3_676 ? C2 H5 0.88(3) . ? C3 C2 1.388(3) 3_676 ? C3 H6 0.93(3) . ? O2 N2 1.226(2) . ? O1 C11 1.257(2) . ? O5 C12 1.293(2) . ? O5 H7 0.97(4) . ? O3 N2 1.223(2) . ? N1 C11 1.322(2) . ? N1 H9 0.86(3) . ? N1 H8 0.86(3) . ? O4 C12 1.220(2) . ? C8 C9 1.397(3) . ? C8 C7 1.398(2) . ? C8 C11 1.492(3) . ? C12 C12 1.546(4) 3_764 ? N2 C5 1.467(3) . ? C10 C9 1.381(3) . ? C10 C5 1.388(3) . ? C10 H2 0.93(2) . ? C9 H1 0.88(2) . ? C5 C6 1.388(3) . ? C6 C7 1.387(3) . ? C6 H3 0.89(3) . ? C7 H4 0.94(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 120.5(2) . . ? C2 C1 I1 119.67(15) . . ? C3 C1 I1 119.80(15) . . ? C1 C2 C3 119.88(19) . 3_676 ? C1 C2 H5 121.8(17) . . ? C3 C2 H5 118.3(17) 3_676 . ? C1 C3 C2 119.60(19) . 3_676 ? C1 C3 H6 118.0(16) . . ? C2 C3 H6 122.4(16) 3_676 . ? C12 O5 H7 110(2) . . ? C11 N1 H9 121.8(16) . . ? C11 N1 H8 121.0(18) . . ? H9 N1 H8 117(2) . . ? C9 C8 C7 119.91(18) . . ? C9 C8 C11 121.18(16) . . ? C7 C8 C11 118.87(16) . . ? O4 C12 O5 126.11(19) . . ? O4 C12 C12 120.7(2) . 3_764 ? O5 C12 C12 113.14(19) . 3_764 ? O3 N2 O2 123.39(18) . . ? O3 N2 C5 118.20(17) . . ? O2 N2 C5 118.41(16) . . ? C9 C10 C5 118.47(17) . . ? C9 C10 H2 122.8(13) . . ? C5 C10 H2 118.7(13) . . ? O1 C11 N1 122.49(18) . . ? O1 C11 C8 119.31(16) . . ? N1 C11 C8 118.20(16) . . ? C10 C9 C8 120.39(17) . . ? C10 C9 H1 116.0(15) . . ? C8 C9 H1 123.6(15) . . ? C10 C5 C6 122.66(19) . . ? C10 C5 N2 118.36(17) . . ? C6 C5 N2 118.97(16) . . ? C7 C6 C5 118.17(18) . . ? C7 C6 H3 120.2(16) . . ? C5 C6 H3 121.6(16) . . ? C6 C7 C8 120.35(17) . . ? C6 C7 H4 121.0(15) . . ? C8 C7 H4 118.6(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C1 C2 C3 -0.2(4) . . . 3_676 ? I1 C1 C2 C3 -179.21(16) . . . 3_676 ? C2 C1 C3 C2 0.2(4) . . . 3_676 ? I1 C1 C3 C2 179.20(16) . . . 3_676 ? C9 C8 C11 O1 -156.16(18) . . . . ? C7 C8 C11 O1 21.6(3) . . . . ? C9 C8 C11 N1 23.9(3) . . . . ? C7 C8 C11 N1 -158.34(18) . . . . ? C5 C10 C9 C8 0.3(3) . . . . ? C7 C8 C9 C10 1.6(3) . . . . ? C11 C8 C9 C10 179.31(18) . . . . ? C9 C10 C5 C6 -1.8(3) . . . . ? C9 C10 C5 N2 178.28(17) . . . . ? O3 N2 C5 C10 176.4(2) . . . . ? O2 N2 C5 C10 -4.0(3) . . . . ? O3 N2 C5 C6 -3.5(3) . . . . ? O2 N2 C5 C6 176.11(19) . . . . ? C10 C5 C6 C7 1.4(3) . . . . ? N2 C5 C6 C7 -178.75(18) . . . . ? C5 C6 C7 C8 0.6(3) . . . . ? C9 C8 C7 C6 -2.1(3) . . . . ? C11 C8 C7 C6 -179.84(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.812 _refine_diff_density_min -0.876 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 940326' ####################################################################### # # 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_platon _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-nitrobenzamide:fumaric acid:1,4-diiodobenzene' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 I N2 O5' _chemical_formula_weight 389.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' I I -0.4740 1.8120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 '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 6.4365(11) _cell_length_b 7.4527(13) _cell_length_c 14.168(3) _cell_angle_alpha 98.844(7) _cell_angle_beta 101.270(7) _cell_angle_gamma 92.395(7) _cell_volume 656.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6814 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.967 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 378 _exptl_absorpt_coefficient_mu 2.459 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.6390 _exptl_absorpt_correction_T_max 0.7911 #=============================================================================== # 7. EXPERIMENTAL DATA _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6887 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3006 _reflns_number_gt 2911 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0211P)^2^+0.8658P] 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 3006 _refine_ls_number_parameters 206 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0252 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0623 _refine_ls_wR_factor_gt 0.0613 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.130 _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 O1 O 0.3933(4) 0.0957(3) 0.17834(18) 0.0346(5) Uani 1 1 d . . . O2 O 0.1289(3) 0.2659(3) 0.17571(18) 0.0360(5) Uani 1 1 d . . . O8 O 1.0929(3) 0.8526(2) 0.36451(14) 0.0206(4) Uani 1 1 d . . . N1 N 0.8209(3) 1.0204(3) 0.39166(17) 0.0198(4) Uani 1 1 d . . . H4 H 0.6893 1.0314 0.3998 0.024 Uiso 1 1 d R . . H3 H 0.9005 1.1273 0.4111 0.024 Uiso 1 1 d R . . N4 N 0.3200(4) 0.2441(3) 0.19267(16) 0.0205(4) Uani 1 1 d . . . C1 C 0.4690(4) 0.4054(3) 0.23309(17) 0.0152(5) Uani 1 1 d . . . C2 C 0.3887(4) 0.5752(4) 0.24032(18) 0.0177(5) Uani 1 1 d . . . C3 C 0.5283(4) 0.7265(3) 0.28058(18) 0.0172(5) Uani 1 1 d . . . C4 C 0.7436(4) 0.7057(3) 0.31382(17) 0.0143(4) Uani 1 1 d . . . C5 C 0.8197(4) 0.5329(3) 0.30459(19) 0.0180(5) Uani 1 1 d . . . C6 C 0.6829(4) 0.3805(3) 0.26319(19) 0.0193(5) Uani 1 1 d . . . C20 C 0.8984(4) 0.8666(3) 0.35864(17) 0.0152(4) Uani 1 1 d . . . I1 I 0.87639(3) 0.86521(2) 0.093400(12) 0.02426(7) Uani 1 1 d . . . C7 C 0.7120(4) 0.4676(4) 0.0298(2) 0.0206(5) Uani 1 1 d . . . C8 C 0.6497(4) 0.6453(4) 0.03783(18) 0.0187(5) Uani 1 1 d . . . C9 C 0.4368(4) 0.6781(4) 0.0079(2) 0.0215(5) Uani 1 1 d . . . O6 O 0.1473(3) 0.3139(3) 0.44778(15) 0.0249(4) Uani 1 1 d . . . O7 O 0.3853(3) 0.1121(3) 0.42019(16) 0.025 Uani 1 1 d D . . C21 C 0.3293(4) 0.2764(3) 0.45013(17) 0.0158(5) Uani 1 1 d . . . C22 C 0.5147(4) 0.4128(3) 0.48839(19) 0.0177(5) Uani 1 1 d . . . H9 H 0.649(5) 0.376(4) 0.499(2) 0.024(8) Uiso 1 1 d . . . H7 H 0.246(5) 0.593(4) 0.218(2) 0.024(8) Uiso 1 1 d . . . H5 H 0.969(6) 0.519(5) 0.326(2) 0.028(9) Uiso 1 1 d . . . H6 H 0.732(6) 0.256(5) 0.256(2) 0.033(9) Uiso 1 1 d . . . H1 H 0.843(6) 0.451(5) 0.050(2) 0.030(9) Uiso 1 1 d . . . H8 H 0.469(6) 0.839(5) 0.281(2) 0.032(9) Uiso 1 1 d . . . H2 H 0.403(6) 0.799(5) 0.012(2) 0.030(9) Uiso 1 1 d . . . H10 H 0.278(5) 0.037(5) 0.400(3) 0.047 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 O1 0.0323(12) 0.0150(9) 0.0502(13) 0.0000(9) -0.0021(10) -0.0022(8) O2 0.0168(10) 0.0299(11) 0.0540(14) -0.0063(10) 0.0022(9) -0.0069(8) O8 0.0108(8) 0.0180(8) 0.0301(10) -0.0019(7) 0.0020(7) -0.0011(7) N1 0.0123(10) 0.0145(9) 0.0300(11) -0.0025(8) 0.0036(9) -0.0011(8) N4 0.0218(11) 0.0177(10) 0.0206(10) 0.0013(8) 0.0037(9) -0.0026(9) C1 0.0161(11) 0.0142(11) 0.0141(10) 0.0000(8) 0.0031(9) -0.0030(9) C2 0.0119(11) 0.0212(12) 0.0191(11) 0.0030(9) 0.0015(9) 0.0003(9) C3 0.0148(11) 0.0149(11) 0.0216(12) 0.0032(9) 0.0023(9) 0.0023(9) C4 0.0127(11) 0.0138(11) 0.0154(10) 0.0014(8) 0.0020(9) -0.0024(9) C5 0.0131(11) 0.0177(11) 0.0221(12) 0.0031(9) 0.0012(9) 0.0016(9) C6 0.0177(12) 0.0150(11) 0.0245(12) 0.0045(10) 0.0016(10) 0.0016(9) C20 0.0138(11) 0.0152(11) 0.0161(11) 0.0027(9) 0.0020(9) 0.0006(9) I1 0.02461(11) 0.02368(10) 0.02243(10) 0.00249(7) 0.00344(7) -0.01031(7) C7 0.0150(12) 0.0233(12) 0.0234(12) 0.0054(10) 0.0026(10) 0.0008(10) C8 0.0191(12) 0.0188(11) 0.0171(11) 0.0022(9) 0.0028(9) -0.0046(10) C9 0.0216(13) 0.0189(12) 0.0244(13) 0.0041(10) 0.0051(10) 0.0010(10) O6 0.0133(9) 0.0167(9) 0.0407(11) -0.0003(8) 0.0002(8) -0.0004(7) O7 0.013 0.015 0.043 -0.005 0.006 -0.002 C21 0.0162(11) 0.0135(10) 0.0165(11) 0.0022(8) 0.0010(9) -0.0012(9) C22 0.0118(11) 0.0192(12) 0.0209(12) 0.0031(9) 0.0014(9) -0.0013(9) _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 O1 N4 1.224(3) . ? O2 N4 1.229(3) . ? O8 C20 1.248(3) . ? N1 C20 1.325(3) . ? N1 H4 0.8822 . ? N1 H3 0.9033 . ? N4 C1 1.473(3) . ? C1 C2 1.384(3) . ? C1 C6 1.389(3) . ? C2 C3 1.386(3) . ? C2 H7 0.93(3) . ? C3 C4 1.397(3) . ? C3 H8 0.94(4) . ? C4 C5 1.394(3) . ? C4 C20 1.501(3) . ? C5 C6 1.385(3) . ? C5 H5 0.96(3) . ? C6 H6 0.99(4) . ? I1 C8 2.095(3) . ? C7 C9 1.385(4) 2_665 ? C7 C8 1.394(4) . ? C7 H1 0.86(4) . ? C8 C9 1.396(4) . ? C9 C7 1.385(4) 2_665 ? C9 H2 0.93(4) . ? O6 C21 1.211(3) . ? O7 C21 1.321(3) . ? O7 H10 0.844(19) . ? C21 C22 1.493(3) . ? C22 C22 1.321(5) 2_666 ? C22 H9 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 N1 H4 125.3 . . ? C20 N1 H3 123.1 . . ? H4 N1 H3 111.6 . . ? O1 N4 O2 123.7(2) . . ? O1 N4 C1 118.2(2) . . ? O2 N4 C1 118.1(2) . . ? C2 C1 C6 122.9(2) . . ? C2 C1 N4 118.4(2) . . ? C6 C1 N4 118.7(2) . . ? C1 C2 C3 118.3(2) . . ? C1 C2 H7 123(2) . . ? C3 C2 H7 119(2) . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H8 116(2) . . ? C4 C3 H8 124(2) . . ? C5 C4 C3 120.1(2) . . ? C5 C4 C20 118.4(2) . . ? C3 C4 C20 121.5(2) . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119(2) . . ? C4 C5 H5 120(2) . . ? C5 C6 C1 118.0(2) . . ? C5 C6 H6 122(2) . . ? C1 C6 H6 120(2) . . ? O8 C20 N1 122.2(2) . . ? O8 C20 C4 120.1(2) . . ? N1 C20 C4 117.7(2) . . ? C9 C7 C8 120.3(2) 2_665 . ? C9 C7 H1 121(2) 2_665 . ? C8 C7 H1 119(2) . . ? C7 C8 C9 120.4(2) . . ? C7 C8 I1 120.02(19) . . ? C9 C8 I1 119.60(19) . . ? C7 C9 C8 119.4(2) 2_665 . ? C7 C9 H2 123(2) 2_665 . ? C8 C9 H2 117(2) . . ? C21 O7 H10 111(3) . . ? O6 C21 O7 124.1(2) . . ? O6 C21 C22 122.9(2) . . ? O7 C21 C22 113.0(2) . . ? C22 C22 C21 120.5(3) 2_666 . ? C22 C22 H9 119(2) 2_666 . ? C21 C22 H9 120(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N4 C1 C2 173.7(2) . . . . ? O2 N4 C1 C2 -6.7(3) . . . . ? O1 N4 C1 C6 -7.0(3) . . . . ? O2 N4 C1 C6 172.6(2) . . . . ? C6 C1 C2 C3 -0.8(4) . . . . ? N4 C1 C2 C3 178.4(2) . . . . ? C1 C2 C3 C4 -0.8(4) . . . . ? C2 C3 C4 C5 1.4(4) . . . . ? C2 C3 C4 C20 -179.4(2) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C20 C4 C5 C6 -179.6(2) . . . . ? C4 C5 C6 C1 -1.1(4) . . . . ? C2 C1 C6 C5 1.8(4) . . . . ? N4 C1 C6 C5 -177.5(2) . . . . ? C5 C4 C20 O8 17.7(3) . . . . ? C3 C4 C20 O8 -161.4(2) . . . . ? C5 C4 C20 N1 -161.8(2) . . . . ? C3 C4 C20 N1 19.1(3) . . . . ? C9 C7 C8 C9 0.0(4) 2_665 . . . ? C9 C7 C8 I1 -179.2(2) 2_665 . . . ? C7 C8 C9 C7 0.0(4) . . . 2_665 ? I1 C8 C9 C7 179.23(19) . . . 2_665 ? O6 C21 C22 C22 -7.6(5) . . . 2_666 ? O7 C21 C22 C22 172.8(3) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.971 _refine_diff_density_min -1.207 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 940327' ####################################################################### # # 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_platon _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H9 Br0.54 I0.44 N2 O5' _chemical_formula_weight 347.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4740 1.8120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.5920(10) _cell_length_b 9.9290(7) _cell_length_c 9.4437(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.381(8) _cell_angle_gamma 90.00 _cell_volume 1216.28(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12266 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description bolock _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.900 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 3.008 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.5845 _exptl_absorpt_correction_T_max 0.7530 #=============================================================================== # 7. EXPERIMENTAL DATA _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12541 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2800 _reflns_number_gt 2691 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0484P)^2^+2.7799P] 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 2800 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.038 _refine_ls_shift/su_mean 0.009 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.38298(18) 0.4218(2) -0.3322(2) 0.0220(5) Uani 1 1 d . . . O5 O -0.2058(2) 0.3712(3) -0.9417(3) 0.0391(7) Uani 1 1 d . . . O6 O -0.1729(2) 0.5848(3) -0.9280(3) 0.0319(6) Uani 1 1 d . . . N1 N -0.2060(2) 0.4819(3) -0.8848(3) 0.0224(6) Uani 1 1 d . . . N3 N -0.4064(2) 0.6456(3) -0.3708(3) 0.0201(5) Uani 1 1 d . . . H1 H -0.4195 0.6521 -0.2918 0.024 Uiso 1 1 d R . . H2 H -0.4069 0.7135 -0.4173 0.024 Uiso 1 1 d R . . C4 C -0.3312(3) 0.5174(3) -0.5287(4) 0.0180(6) Uani 1 1 d . . . C5 C -0.2433(2) 0.6166(3) -0.6897(3) 0.0180(6) Uani 1 1 d . . . H24 H -0.2120 0.6918 -0.7211 0.022 Uiso 1 1 calc R . . C6 C -0.2921(2) 0.3796(3) -0.7166(3) 0.0194(6) Uani 1 1 d . . . H22 H -0.2943 0.2962 -0.7666 0.023 Uiso 1 1 calc R . . C7 C -0.2480(2) 0.4927(3) -0.7589(4) 0.0173(6) Uani 1 1 d . . . C8 C -0.3760(2) 0.5270(3) -0.4023(3) 0.0165(6) Uani 1 1 d . . . C9 C -0.2853(2) 0.6282(3) -0.5738(3) 0.0175(6) Uani 1 1 d . . . H23 H -0.2829 0.7122 -0.5247 0.021 Uiso 1 1 calc R . . C10 C -0.3329(2) 0.3923(3) -0.5990(3) 0.0178(6) Uani 1 1 d . . . H21 H -0.3621 0.3160 -0.5659 0.021 Uiso 1 1 calc R . . I2 I -0.09171(10) 0.52872(11) -0.20572(14) 0.0192(3) Uiso 0.44 1 d P . . Br2 Br -0.09730(10) 0.50083(15) -0.21082(13) 0.0176(3) Uani 0.54 1 d P . . C1 C -0.0395(3) 0.5071(3) -0.3813(4) 0.0256(7) Uani 1 1 d . . . C2 C -0.0014(3) 0.6230(4) -0.4295(4) 0.0300(7) Uani 1 1 d . . . H5 H -0.0025 0.7065 -0.3810 0.036 Uiso 1 1 calc R . . C3 C -0.0382(3) 0.3844(4) -0.4509(4) 0.0289(7) Uani 1 1 d . . . H4 H -0.0642 0.3059 -0.4171 0.035 Uiso 1 1 calc R . . O3 O -0.4354(2) -0.1202(2) -0.5741(3) 0.0250(5) Uani 1 1 d . . . O4 O -0.47361(18) 0.0946(2) -0.6399(2) 0.0214(5) Uani 1 1 d . . . H3 H -0.4380 0.0790 -0.6946 0.032 Uiso 1 1 d R . . C21 C -0.4733(2) -0.0107(3) -0.5601(3) 0.0132(5) 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 O1 0.0298(12) 0.0176(11) 0.0245(11) 0.0034(8) 0.0170(9) 0.0015(9) O5 0.0524(18) 0.0349(15) 0.0407(15) -0.0123(12) 0.0301(13) -0.0045(13) O6 0.0397(15) 0.0315(14) 0.0334(13) 0.0096(10) 0.0246(11) 0.0038(11) N1 0.0217(15) 0.0272(14) 0.0211(14) 0.0004(10) 0.0105(11) 0.0036(11) N3 0.0258(14) 0.0183(12) 0.0195(12) 0.0025(9) 0.0117(10) 0.0021(10) C4 0.0170(15) 0.0204(14) 0.0176(14) 0.0000(11) 0.0066(12) 0.0029(11) C5 0.0156(14) 0.0177(14) 0.0213(14) 0.0032(11) 0.0062(11) -0.0009(11) C6 0.0225(15) 0.0164(14) 0.0220(14) -0.0035(11) 0.0107(12) -0.0004(12) C7 0.0143(15) 0.0234(15) 0.0157(14) 0.0018(10) 0.0066(12) 0.0020(11) C8 0.0135(13) 0.0195(14) 0.0176(14) 0.0014(10) 0.0061(11) -0.0016(10) C9 0.0172(14) 0.0191(14) 0.0168(13) -0.0012(10) 0.0059(11) 0.0019(11) C10 0.0175(14) 0.0173(13) 0.0200(13) 0.0013(11) 0.0080(11) 0.0006(11) Br2 0.0193(4) 0.0206(6) 0.0161(4) 0.0005(4) 0.0101(3) -0.0001(4) C1 0.0205(17) 0.0313(18) 0.0221(16) 0.0051(12) 0.0019(13) 0.0007(13) C2 0.0276(18) 0.0258(17) 0.0325(18) 0.0010(13) 0.0027(14) -0.0014(14) C3 0.0219(16) 0.0265(17) 0.0345(18) 0.0077(14) 0.0026(13) -0.0020(13) O3 0.0359(13) 0.0214(11) 0.0241(11) 0.0043(9) 0.0189(10) 0.0100(10) O4 0.0303(12) 0.0174(10) 0.0230(11) 0.0020(8) 0.0181(9) 0.0020(9) C21 0.0107(13) 0.0155(13) 0.0145(14) 0.0002(9) 0.0053(11) -0.0017(10) _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 O1 C8 1.255(4) . ? O5 N1 1.224(4) . ? O6 N1 1.234(4) . ? N1 C7 1.468(4) . ? N3 C8 1.311(4) . ? N3 H1 0.8197 . ? N3 H2 0.8028 . ? C4 C9 1.393(4) . ? C4 C10 1.405(4) . ? C4 C8 1.497(4) . ? C5 C9 1.381(4) . ? C5 C7 1.385(4) . ? C5 H24 0.9500 . ? C6 C10 1.388(4) . ? C6 C7 1.386(4) . ? C6 H22 0.9500 . ? C9 H23 0.9500 . ? C10 H21 0.9500 . ? I2 C1 2.001(4) . ? Br2 C1 1.992(4) . ? C1 C3 1.387(5) . ? C1 C2 1.392(5) . ? C2 C3 1.390(6) 3_564 ? C2 H5 0.9500 . ? C3 C2 1.390(6) 3_564 ? C3 H4 0.9500 . ? O3 C21 1.227(4) . ? O4 C21 1.288(3) . ? O4 H3 0.8217 . ? C21 C21 1.533(6) 3_454 ? 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 O5 N1 O6 123.3(3) . . ? O5 N1 C7 118.3(3) . . ? O6 N1 C7 118.4(3) . . ? C8 N3 H1 116.5 . . ? C8 N3 H2 125.6 . . ? H1 N3 H2 117.5 . . ? C9 C4 C10 120.0(3) . . ? C9 C4 C8 121.3(3) . . ? C10 C4 C8 118.7(3) . . ? C9 C5 C7 118.5(3) . . ? C9 C5 H24 120.8 . . ? C7 C5 H24 120.8 . . ? C10 C6 C7 117.9(3) . . ? C10 C6 H22 121.1 . . ? C7 C6 H22 121.1 . . ? C5 C7 C6 123.1(3) . . ? C5 C7 N1 118.3(3) . . ? C6 C7 N1 118.7(3) . . ? O1 C8 N3 123.3(3) . . ? O1 C8 C4 118.7(3) . . ? N3 C8 C4 118.0(3) . . ? C5 C9 C4 120.3(3) . . ? C5 C9 H23 119.8 . . ? C4 C9 H23 119.8 . . ? C6 C10 C4 120.3(3) . . ? C6 C10 H21 119.9 . . ? C4 C10 H21 119.9 . . ? C3 C1 C2 120.8(4) . . ? C3 C1 Br2 114.8(3) . . ? C2 C1 Br2 124.4(3) . . ? C3 C1 I2 123.0(3) . . ? C2 C1 I2 116.2(3) . . ? Br2 C1 I2 8.25(6) . . ? C3 C2 C1 119.6(3) 3_564 . ? C3 C2 H5 120.2 3_564 . ? C1 C2 H5 120.2 . . ? C1 C3 C2 119.6(3) . 3_564 ? C1 C3 H4 120.2 . . ? C2 C3 H4 120.2 3_564 . ? C21 O4 H3 108.5 . . ? O3 C21 O4 125.7(3) . . ? O3 C21 C21 120.6(3) . 3_454 ? O4 C21 C21 113.7(3) . 3_454 ? 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 C9 C5 C7 C6 -0.5(5) . . . . ? C9 C5 C7 N1 178.2(3) . . . . ? C10 C6 C7 C5 -0.2(5) . . . . ? C10 C6 C7 N1 -178.9(3) . . . . ? O5 N1 C7 C5 176.7(3) . . . . ? O6 N1 C7 C5 -3.3(4) . . . . ? O5 N1 C7 C6 -4.5(5) . . . . ? O6 N1 C7 C6 175.4(3) . . . . ? C9 C4 C8 O1 -155.2(3) . . . . ? C10 C4 C8 O1 22.7(4) . . . . ? C9 C4 C8 N3 24.9(5) . . . . ? C10 C4 C8 N3 -157.2(3) . . . . ? C7 C5 C9 C4 -0.1(4) . . . . ? C10 C4 C9 C5 1.4(5) . . . . ? C8 C4 C9 C5 179.3(3) . . . . ? C7 C6 C10 C4 1.6(5) . . . . ? C9 C4 C10 C6 -2.1(5) . . . . ? C8 C4 C10 C6 179.9(3) . . . . ? C3 C1 C2 C3 0.1(6) . . . 3_564 ? Br2 C1 C2 C3 179.4(3) . . . 3_564 ? I2 C1 C2 C3 178.7(3) . . . 3_564 ? C2 C1 C3 C2 -0.1(6) . . . 3_564 ? Br2 C1 C3 C2 -179.5(3) . . . 3_564 ? I2 C1 C3 C2 -178.6(3) . . . 3_564 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.015 _refine_diff_density_min -1.107 _refine_diff_density_rms 0.093 _database_code_depnum_ccdc_archive 'CCDC 940328' ####################################################################### # # 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_platon _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-nitrobenzamide: adipic acid' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 N2 O5' _chemical_formula_weight 239.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.3620(9) _cell_length_b 13.8657(19) _cell_length_c 13.6664(17) _cell_angle_alpha 90.00 _cell_angle_beta 116.646(7) _cell_angle_gamma 90.00 _cell_volume 1077.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9822 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour 'colour less' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.120 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9649 _exptl_absorpt_correction_T_max 0.9881 #=============================================================================== # 7. EXPERIMENTAL DATA _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10650 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2464 _reflns_number_gt 2191 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0401P)^2^+0.3938P] 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_number_reflns 2464 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 O1 O 0.67794(16) 0.38141(7) 1.06882(7) 0.0295(2) Uani 1 1 d . . . O2 O 0.55541(17) 0.29140(6) 0.91761(7) 0.0297(2) Uani 1 1 d . . . H11 H 0.5246 0.2471 0.9596 0.045 Uiso 1 1 d R . . C5 C 0.8764(2) 0.52129(8) 0.97637(10) 0.0233(3) Uani 1 1 d . . . H7 H 0.8448 0.5443 1.0371 0.028 Uiso 1 1 calc R . . H8 H 0.8676 0.5776 0.9301 0.028 Uiso 1 1 calc R . . C8 C 0.64420(19) 0.37133(8) 0.97456(9) 0.0202(2) Uani 1 1 d . . . C10 C 0.6882(2) 0.44839(9) 0.90807(10) 0.0247(3) Uani 1 1 d . . . H9 H 0.5392 0.4833 0.8646 0.030 Uiso 1 1 calc R . . H10 H 0.7359 0.4170 0.8560 0.030 Uiso 1 1 calc R . . O3 O 0.00465(18) 0.72922(7) 0.69018(9) 0.0380(3) Uani 1 1 d . . . O4 O -0.20015(16) 0.62992(7) 0.73565(7) 0.0330(2) Uani 1 1 d . . . O5 O 0.44679(16) 0.34616(6) 0.51988(7) 0.0258(2) Uani 1 1 d . . . N1 N -0.05415(18) 0.64744(8) 0.70218(8) 0.0262(2) Uani 1 1 d . . . N2 N 0.4306(2) 0.25276(8) 0.65145(9) 0.0292(3) Uani 1 1 d . . . H1 H 0.4039 0.2469 0.7055 0.035 Uiso 1 1 d R . . H2 H 0.5067 0.2044 0.6363 0.035 Uiso 1 1 d R . . C1 C 0.2080(2) 0.58540(8) 0.62923(9) 0.0215(2) Uani 1 1 d . . . H5 H 0.2392 0.6500 0.6166 0.026 Uiso 1 1 calc R . . C2 C 0.38915(19) 0.33416(8) 0.59488(9) 0.0186(2) Uani 1 1 d . . . C3 C 0.31225(19) 0.50857(8) 0.60268(9) 0.0194(2) Uani 1 1 d . . . H6 H 0.4138 0.5202 0.5700 0.023 Uiso 1 1 calc R . . C4 C 0.0568(2) 0.56544(8) 0.67465(9) 0.0207(2) Uani 1 1 d . . . C6 C 0.1154(2) 0.39643(9) 0.66977(9) 0.0220(2) Uani 1 1 d . . . H3 H 0.0856 0.3320 0.6838 0.026 Uiso 1 1 calc R . . C7 C 0.26858(19) 0.41426(8) 0.62381(8) 0.0176(2) Uani 1 1 d . . . C9 C 0.0069(2) 0.47272(9) 0.69489(9) 0.0233(2) Uani 1 1 d . . . H4 H -0.0991 0.4615 0.7253 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0377(5) 0.0306(5) 0.0219(4) -0.0044(3) 0.0148(4) -0.0137(4) O2 0.0445(5) 0.0242(4) 0.0287(5) -0.0063(4) 0.0237(4) -0.0131(4) C5 0.0239(6) 0.0204(6) 0.0245(6) 0.0017(4) 0.0098(5) -0.0052(4) C8 0.0172(5) 0.0212(5) 0.0221(5) -0.0014(4) 0.0088(4) -0.0034(4) C10 0.0244(6) 0.0269(6) 0.0197(5) 0.0018(4) 0.0070(5) -0.0072(5) O3 0.0415(6) 0.0258(5) 0.0514(6) -0.0100(4) 0.0249(5) 0.0028(4) O4 0.0304(5) 0.0464(6) 0.0278(5) -0.0012(4) 0.0179(4) 0.0108(4) O5 0.0387(5) 0.0203(4) 0.0285(5) 0.0027(3) 0.0242(4) 0.0047(4) N1 0.0241(5) 0.0325(6) 0.0208(5) -0.0052(4) 0.0090(4) 0.0059(4) N2 0.0431(6) 0.0244(5) 0.0307(6) 0.0096(4) 0.0259(5) 0.0125(5) C1 0.0243(5) 0.0192(5) 0.0217(5) -0.0017(4) 0.0110(4) -0.0010(4) C2 0.0188(5) 0.0192(5) 0.0180(5) -0.0002(4) 0.0084(4) -0.0005(4) C3 0.0203(5) 0.0214(5) 0.0188(5) -0.0010(4) 0.0109(4) -0.0015(4) C4 0.0199(5) 0.0251(6) 0.0160(5) -0.0031(4) 0.0071(4) 0.0034(4) C6 0.0248(6) 0.0222(6) 0.0216(5) 0.0031(4) 0.0127(5) -0.0005(4) C7 0.0181(5) 0.0200(5) 0.0140(5) -0.0004(4) 0.0066(4) 0.0008(4) C9 0.0222(5) 0.0312(6) 0.0208(5) 0.0013(5) 0.0135(5) 0.0011(5) _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 O1 C8 1.2154(14) . ? O2 C8 1.3262(14) . ? O2 H11 0.9196 . ? C5 C10 1.5245(16) . ? C5 C5 1.526(2) 3_767 ? C5 H7 0.9900 . ? C5 H8 0.9900 . ? C8 C10 1.5080(16) . ? C10 H9 0.9900 . ? C10 H10 0.9900 . ? O3 N1 1.2278(15) . ? O4 N1 1.2297(14) . ? O5 C2 1.2450(13) . ? N1 C4 1.4735(15) . ? N2 C2 1.3259(15) . ? N2 H1 0.8331 . ? N2 H2 0.9033 . ? C1 C4 1.3862(16) . ? C1 C3 1.3867(16) . ? C1 H5 0.9500 . ? C2 C7 1.5002(15) . ? C3 C7 1.3937(16) . ? C3 H6 0.9500 . ? C4 C9 1.3817(17) . ? C6 C9 1.3878(17) . ? C6 C7 1.3979(15) . ? C6 H3 0.9500 . ? C9 H4 0.9500 . ? 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 C8 O2 H11 110.2 . . ? C10 C5 C5 112.33(12) . 3_767 ? C10 C5 H7 109.1 . . ? C5 C5 H7 109.1 3_767 . ? C10 C5 H8 109.1 . . ? C5 C5 H8 109.1 3_767 . ? H7 C5 H8 107.9 . . ? O1 C8 O2 122.99(11) . . ? O1 C8 C10 124.40(11) . . ? O2 C8 C10 112.57(10) . . ? C8 C10 C5 114.07(10) . . ? C8 C10 H9 108.7 . . ? C5 C10 H9 108.7 . . ? C8 C10 H10 108.7 . . ? C5 C10 H10 108.7 . . ? H9 C10 H10 107.6 . . ? O3 N1 O4 123.95(11) . . ? O3 N1 C4 117.96(10) . . ? O4 N1 C4 118.09(11) . . ? C2 N2 H1 122.2 . . ? C2 N2 H2 119.0 . . ? H1 N2 H2 118.4 . . ? C4 C1 C3 118.24(11) . . ? C4 C1 H5 120.9 . . ? C3 C1 H5 120.9 . . ? O5 C2 N2 122.60(10) . . ? O5 C2 C7 119.49(10) . . ? N2 C2 C7 117.91(10) . . ? C1 C3 C7 120.22(10) . . ? C1 C3 H6 119.9 . . ? C7 C3 H6 119.9 . . ? C9 C4 C1 122.91(10) . . ? C9 C4 N1 119.17(10) . . ? C1 C4 N1 117.92(11) . . ? C9 C6 C7 120.04(11) . . ? C9 C6 H3 120.0 . . ? C7 C6 H3 120.0 . . ? C3 C7 C6 120.20(10) . . ? C3 C7 C2 117.84(10) . . ? C6 C7 C2 121.96(10) . . ? C4 C9 C6 118.37(10) . . ? C4 C9 H4 120.8 . . ? C6 C9 H4 120.8 . . ? 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 C8 C10 C5 26.78(17) . . . . ? O2 C8 C10 C5 -155.59(10) . . . . ? C5 C5 C10 C8 72.81(16) 3_767 . . . ? C4 C1 C3 C7 -1.38(17) . . . . ? C3 C1 C4 C9 0.30(17) . . . . ? C3 C1 C4 N1 -179.73(10) . . . . ? O3 N1 C4 C9 175.31(11) . . . . ? O4 N1 C4 C9 -4.78(16) . . . . ? O3 N1 C4 C1 -4.67(16) . . . . ? O4 N1 C4 C1 175.25(10) . . . . ? C1 C3 C7 C6 1.37(17) . . . . ? C1 C3 C7 C2 -179.10(10) . . . . ? C9 C6 C7 C3 -0.24(17) . . . . ? C9 C6 C7 C2 -179.76(10) . . . . ? O5 C2 C7 C3 -27.03(15) . . . . ? N2 C2 C7 C3 152.77(11) . . . . ? O5 C2 C7 C6 152.50(11) . . . . ? N2 C2 C7 C6 -27.71(16) . . . . ? C1 C4 C9 C6 0.80(17) . . . . ? N1 C4 C9 C6 -179.17(10) . . . . ? C7 C6 C9 C4 -0.82(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.340 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 940329' ####################################################################### # # 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_platon _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-nitrobenzamide: benzoic acid' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 N2 O5' _chemical_formula_weight 288.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M ' P 21/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3472(12) _cell_length_b 19.841(3) _cell_length_c 9.2185(15) _cell_angle_alpha 90.00 _cell_angle_beta 106.837(7) _cell_angle_gamma 90.00 _cell_volume 1286.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8432 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.7 _exptl_crystal_description block _exptl_crystal_colour 'colour less' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.115 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9773 _exptl_absorpt_correction_T_max 0.9886 #=============================================================================== # 7. EXPERIMENTAL DATA _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11132 _diffrn_reflns_av_R_equivalents 0.0733 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2927 _reflns_number_gt 1929 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0616P)^2^+0.5660P] 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 2927 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1438 _refine_ls_wR_factor_gt 0.1275 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 O1 O -0.0011(3) 0.07565(9) -0.66584(18) 0.0378(5) Uani 1 1 d . . . O2 O 0.4491(3) 0.09322(8) 0.09706(18) 0.0374(5) Uani 1 1 d . . . O6 O 0.1188(3) 0.17169(9) -0.7005(2) 0.0472(5) Uani 1 1 d . . . N3 N 0.1000(3) 0.12454(10) -0.6194(2) 0.0295(5) Uani 1 1 d . . . N8 N 0.5966(3) 0.18946(9) 0.0708(2) 0.0278(5) Uani 1 1 d . . . H1 H 0.6465 0.1933 0.1748 0.033 Uiso 1 1 d R . . H2 H 0.6274 0.2182 0.0145 0.033 Uiso 1 1 d R . . C1 C 0.3769(3) 0.19197(11) -0.2447(3) 0.0254(5) Uani 1 1 d . . . H6 H 0.4327 0.2333 -0.2018 0.030 Uiso 1 1 calc R . . C3 C 0.2038(3) 0.12776(11) -0.4569(2) 0.0242(5) Uani 1 1 d . . . C4 C 0.2130(3) 0.07057(11) -0.3690(2) 0.0253(5) Uani 1 1 d . . . H4 H 0.1566 0.0295 -0.4127 0.030 Uiso 1 1 calc R . . C5 C 0.2840(3) 0.18822(11) -0.3977(2) 0.0262(5) Uani 1 1 d . . . H5 H 0.2756 0.2266 -0.4609 0.031 Uiso 1 1 calc R . . C9 C 0.3066(3) 0.07492(11) -0.2157(2) 0.0259(5) Uani 1 1 d . . . H3 H 0.3147 0.0364 -0.1529 0.031 Uiso 1 1 calc R . . C11 C 0.3891(3) 0.13542(11) -0.1528(2) 0.0234(5) Uani 1 1 d . . . C19 C 0.4832(3) 0.13804(11) 0.0144(2) 0.0255(5) Uani 1 1 d . . . O4 O -0.4241(2) 0.08221(8) -0.61283(17) 0.0324(4) Uani 1 1 d . . . H7 H -0.4657 0.0908 -0.7046 0.049 Uiso 1 1 d R . . O5 O -0.3007(2) 0.18606(8) -0.59318(17) 0.0308(4) Uani 1 1 d . . . C2 C -0.3257(3) 0.13241(11) -0.5355(2) 0.0244(5) Uani 1 1 d . . . C6 C -0.2460(3) 0.11866(11) -0.3708(2) 0.0223(5) Uani 1 1 d . . . C7 C -0.0689(3) 0.15673(12) -0.1229(3) 0.0305(6) Uani 1 1 d . . . H9 H 0.0016 0.1908 -0.0582 0.037 Uiso 1 1 calc R . . C8 C -0.0988(4) 0.09534(13) -0.0630(3) 0.0326(6) Uani 1 1 d . . . H10 H -0.0491 0.0875 0.0428 0.039 Uiso 1 1 calc R . . C10 C -0.2758(3) 0.05661(11) -0.3100(3) 0.0265(5) Uani 1 1 d . . . H12 H -0.3470 0.0224 -0.3739 0.032 Uiso 1 1 calc R . . C12 C -0.2008(3) 0.04518(12) -0.1560(3) 0.0312(6) Uani 1 1 d . . . H11 H -0.2193 0.0029 -0.1142 0.037 Uiso 1 1 calc R . . C13 C -0.1409(3) 0.16875(11) -0.2762(3) 0.0261(5) Uani 1 1 d . . . H8 H -0.1191 0.2109 -0.3173 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0475(12) 0.0337(10) 0.0280(9) -0.0039(7) 0.0042(8) -0.0096(9) O2 0.0517(12) 0.0338(10) 0.0238(9) 0.0033(7) 0.0063(8) -0.0131(9) O6 0.0633(14) 0.0446(11) 0.0269(10) 0.0101(8) 0.0021(9) -0.0155(10) N3 0.0328(12) 0.0298(11) 0.0245(10) -0.0004(8) 0.0063(9) -0.0023(10) N8 0.0369(12) 0.0256(10) 0.0200(10) -0.0006(8) 0.0067(8) -0.0038(9) C1 0.0261(13) 0.0220(11) 0.0279(12) -0.0012(9) 0.0074(10) -0.0009(10) C3 0.0236(13) 0.0275(12) 0.0218(11) 0.0000(9) 0.0072(9) 0.0009(10) C4 0.0268(13) 0.0203(11) 0.0285(12) -0.0017(9) 0.0075(10) -0.0009(10) C5 0.0285(14) 0.0243(12) 0.0259(12) 0.0035(9) 0.0077(10) -0.0009(10) C9 0.0279(14) 0.0233(12) 0.0275(12) 0.0028(9) 0.0095(10) 0.0016(10) C11 0.0216(12) 0.0246(12) 0.0248(12) 0.0002(9) 0.0078(9) 0.0016(9) C19 0.0277(13) 0.0245(12) 0.0250(12) -0.0005(9) 0.0087(10) 0.0033(10) O4 0.0439(11) 0.0294(9) 0.0206(8) 0.0013(7) 0.0040(8) -0.0082(8) O5 0.0438(11) 0.0230(9) 0.0252(9) 0.0026(7) 0.0094(8) -0.0016(8) C2 0.0241(13) 0.0217(11) 0.0275(12) 0.0008(9) 0.0079(10) 0.0025(10) C6 0.0198(12) 0.0238(11) 0.0234(11) -0.0006(9) 0.0061(9) 0.0041(9) C7 0.0249(14) 0.0340(14) 0.0309(13) -0.0062(10) 0.0052(10) 0.0022(11) C8 0.0318(14) 0.0428(15) 0.0233(12) 0.0034(11) 0.0082(10) 0.0065(12) C10 0.0248(13) 0.0257(12) 0.0290(12) 0.0001(9) 0.0079(10) -0.0007(10) C12 0.0339(15) 0.0315(13) 0.0294(13) 0.0081(10) 0.0110(11) 0.0046(11) C13 0.0253(13) 0.0242(11) 0.0298(13) -0.0013(9) 0.0094(10) 0.0016(10) _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 O1 N3 1.221(2) . ? O2 C19 1.243(3) . ? O6 N3 1.230(2) . ? N3 C3 1.473(3) . ? N8 C19 1.324(3) . ? N8 H1 0.9254 . ? N8 H2 0.8448 . ? C1 C5 1.379(3) . ? C1 C11 1.393(3) . ? C1 H6 0.9500 . ? C3 C5 1.378(3) . ? C3 C4 1.385(3) . ? C4 C9 1.384(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C9 C11 1.393(3) . ? C9 H3 0.9500 . ? C11 C19 1.496(3) . ? O4 C2 1.313(3) . ? O4 H7 0.8297 . ? O5 C2 1.227(3) . ? C2 C6 1.486(3) . ? C6 C10 1.396(3) . ? C6 C13 1.398(3) . ? C7 C13 1.378(3) . ? C7 C8 1.381(3) . ? C7 H9 0.9500 . ? C8 C12 1.384(3) . ? C8 H10 0.9500 . ? C10 C12 1.384(3) . ? C10 H12 0.9500 . ? C12 H11 0.9500 . ? C13 H8 0.9500 . ? 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 O1 N3 O6 123.7(2) . . ? O1 N3 C3 118.30(19) . . ? O6 N3 C3 117.9(2) . . ? C19 N8 H1 119.0 . . ? C19 N8 H2 121.9 . . ? H1 N8 H2 119.0 . . ? C5 C1 C11 120.3(2) . . ? C5 C1 H6 119.9 . . ? C11 C1 H6 119.9 . . ? C5 C3 C4 122.6(2) . . ? C5 C3 N3 118.50(19) . . ? C4 C3 N3 118.9(2) . . ? C3 C4 C9 118.2(2) . . ? C3 C4 H4 120.9 . . ? C9 C4 H4 120.9 . . ? C1 C5 C3 118.7(2) . . ? C1 C5 H5 120.6 . . ? C3 C5 H5 120.6 . . ? C4 C9 C11 120.4(2) . . ? C4 C9 H3 119.8 . . ? C11 C9 H3 119.8 . . ? C1 C11 C9 119.8(2) . . ? C1 C11 C19 121.8(2) . . ? C9 C11 C19 118.3(2) . . ? O2 C19 N8 121.8(2) . . ? O2 C19 C11 119.4(2) . . ? N8 C19 C11 118.8(2) . . ? C2 O4 H7 112.4 . . ? O5 C2 O4 123.4(2) . . ? O5 C2 C6 122.6(2) . . ? O4 C2 C6 114.06(19) . . ? C10 C6 C13 119.9(2) . . ? C10 C6 C2 120.7(2) . . ? C13 C6 C2 119.3(2) . . ? C13 C7 C8 120.3(2) . . ? C13 C7 H9 119.9 . . ? C8 C7 H9 119.9 . . ? C7 C8 C12 120.4(2) . . ? C7 C8 H10 119.8 . . ? C12 C8 H10 119.8 . . ? C12 C10 C6 119.6(2) . . ? C12 C10 H12 120.2 . . ? C6 C10 H12 120.2 . . ? C10 C12 C8 120.1(2) . . ? C10 C12 H11 120.0 . . ? C8 C12 H11 120.0 . . ? C7 C13 C6 119.7(2) . . ? C7 C13 H8 120.2 . . ? C6 C13 H8 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N3 C3 C5 -166.1(2) . . . . ? O6 N3 C3 C5 13.2(3) . . . . ? O1 N3 C3 C4 12.3(3) . . . . ? O6 N3 C3 C4 -168.4(2) . . . . ? C5 C3 C4 C9 0.1(4) . . . . ? N3 C3 C4 C9 -178.3(2) . . . . ? C11 C1 C5 C3 0.2(3) . . . . ? C4 C3 C5 C1 -0.1(4) . . . . ? N3 C3 C5 C1 178.2(2) . . . . ? C3 C4 C9 C11 -0.1(3) . . . . ? C5 C1 C11 C9 -0.2(3) . . . . ? C5 C1 C11 C19 -178.0(2) . . . . ? C4 C9 C11 C1 0.2(3) . . . . ? C4 C9 C11 C19 178.1(2) . . . . ? C1 C11 C19 O2 161.3(2) . . . . ? C9 C11 C19 O2 -16.5(3) . . . . ? C1 C11 C19 N8 -16.6(3) . . . . ? C9 C11 C19 N8 165.5(2) . . . . ? O5 C2 C6 C10 -179.2(2) . . . . ? O4 C2 C6 C10 0.7(3) . . . . ? O5 C2 C6 C13 1.1(3) . . . . ? O4 C2 C6 C13 -179.03(19) . . . . ? C13 C7 C8 C12 0.2(4) . . . . ? C13 C6 C10 C12 0.0(3) . . . . ? C2 C6 C10 C12 -179.7(2) . . . . ? C6 C10 C12 C8 0.7(4) . . . . ? C7 C8 C12 C10 -0.9(4) . . . . ? C8 C7 C13 C6 0.6(3) . . . . ? C10 C6 C13 C7 -0.7(3) . . . . ? C2 C6 C13 C7 179.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.223 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 940330' ####################################################################### # # 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_datam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-nitrobenzamide: succinic acid' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 N2 O5' _chemical_formula_weight 225.18 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 31.134(8) _cell_length_b 5.1606(13) _cell_length_c 12.670(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.206(7) _cell_angle_gamma 90.00 _cell_volume 1944.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9260 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour 'colour less' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.128 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9749 _exptl_absorpt_correction_T_max 0.9873 #=============================================================================== # 7. EXPERIMENTAL DATA _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9806 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2235 _reflns_number_gt 2020 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0431P)^2^+1.3160P] 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 2235 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 H4 H 0.3795(5) 0.525(3) 0.8074(11) 0.022(3) Uiso 1 1 d . . . H5 H 0.3320(5) 0.200(3) 0.8348(12) 0.026(4) Uiso 1 1 d . . . H7 H 0.3378(5) 0.378(3) 0.4762(11) 0.024(3) Uiso 1 1 d . . . H6 H 0.2886(5) 0.055(3) 0.5052(12) 0.026(4) Uiso 1 1 d . . . H3 H 0.4145(5) 0.830(3) 0.7613(13) 0.032(4) Uiso 1 1 d . . . H9 H 0.4596(5) 1.539(3) 0.4101(12) 0.036(4) Uiso 1 1 d . . . H8 H 0.4964(5) 1.334(3) 0.4068(13) 0.035(4) Uiso 1 1 d . . . H2 H 0.4356(5) 0.954(4) 0.6765(13) 0.041(4) Uiso 1 1 d . . . H1 H 0.4162(6) 0.968(4) 0.4693(15) 0.056(5) Uiso 1 1 d . . . O3 O 0.39561(3) 0.70707(17) 0.51603(6) 0.0255(2) Uani 1 1 d . . . O2 O 0.28463(3) -0.18357(17) 0.78711(7) 0.0271(2) Uani 1 1 d . . . O1 O 0.24717(3) -0.17865(18) 0.61328(7) 0.0311(2) Uani 1 1 d . . . O4 O 0.42749(3) 1.09784(18) 0.43581(7) 0.0267(2) Uani 1 1 d . . . C7 C 0.30718(3) 0.1030(2) 0.67291(9) 0.0176(2) Uani 1 1 d . . . C4 C 0.36324(4) 0.4816(2) 0.63711(8) 0.0172(2) Uani 1 1 d . . . O5 O 0.47090(4) 1.1784(2) 0.60653(7) 0.0403(3) Uani 1 1 d . . . N1 N 0.41684(3) 0.8359(2) 0.69353(8) 0.0224(2) Uani 1 1 d . . . N2 N 0.27741(3) -0.10187(18) 0.69270(8) 0.0200(2) Uani 1 1 d . . . C6 C 0.33347(4) 0.2381(2) 0.76273(9) 0.0191(2) Uani 1 1 d . . . C5 C 0.36149(4) 0.4306(2) 0.74425(9) 0.0189(2) Uani 1 1 d . . . C9 C 0.33633(4) 0.3404(2) 0.54858(9) 0.0207(2) Uani 1 1 d . . . C3 C 0.39334(4) 0.6852(2) 0.61236(9) 0.0180(2) Uani 1 1 d . . . C8 C 0.30759(4) 0.1499(2) 0.56555(9) 0.0210(2) Uani 1 1 d . . . C2 C 0.46017(4) 1.2235(2) 0.50897(9) 0.0219(2) Uani 1 1 d . . . C1 C 0.48253(4) 1.4241(2) 0.45713(9) 0.0233(3) 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 O3 0.0338(5) 0.0262(4) 0.0180(4) -0.0010(3) 0.0099(3) -0.0118(4) O2 0.0321(5) 0.0243(4) 0.0275(4) 0.0070(4) 0.0126(4) -0.0022(4) O1 0.0324(5) 0.0332(5) 0.0288(5) -0.0092(4) 0.0105(4) -0.0162(4) O4 0.0316(5) 0.0277(4) 0.0195(4) 0.0015(3) 0.0057(3) -0.0137(4) C7 0.0169(5) 0.0152(5) 0.0221(5) 0.0012(4) 0.0079(4) 0.0001(4) C4 0.0178(5) 0.0164(5) 0.0180(5) 0.0011(4) 0.0060(4) 0.0002(4) O5 0.0464(6) 0.0476(6) 0.0211(4) 0.0073(4) 0.0011(4) -0.0278(5) N1 0.0268(5) 0.0231(5) 0.0182(5) -0.0010(4) 0.0079(4) -0.0080(4) N2 0.0219(5) 0.0167(4) 0.0242(5) -0.0017(4) 0.0113(4) -0.0007(4) C6 0.0203(5) 0.0222(5) 0.0162(5) 0.0008(4) 0.0077(4) 0.0001(4) C5 0.0191(5) 0.0206(5) 0.0167(5) -0.0022(4) 0.0049(4) -0.0023(4) C9 0.0249(6) 0.0224(5) 0.0148(5) 0.0008(4) 0.0061(4) -0.0027(4) C3 0.0190(5) 0.0174(5) 0.0175(5) 0.0020(4) 0.0054(4) 0.0005(4) C8 0.0226(5) 0.0215(5) 0.0179(5) -0.0026(4) 0.0045(4) -0.0040(4) C2 0.0234(5) 0.0214(5) 0.0213(5) 0.0013(4) 0.0071(4) -0.0044(4) C1 0.0256(6) 0.0237(6) 0.0208(5) 0.0025(5) 0.0073(5) -0.0075(5) _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 O3 C3 1.2484(13) . ? O2 N2 1.2248(13) . ? O1 N2 1.2229(13) . ? O4 C2 1.3256(14) . ? O4 H1 0.92(2) . ? C7 C6 1.3785(15) . ? C7 C8 1.3854(15) . ? C7 N2 1.4754(14) . ? C4 C9 1.3910(15) . ? C4 C5 1.3994(15) . ? C4 C3 1.5017(15) . ? O5 C2 1.2039(14) . ? N1 C3 1.3236(14) . ? N1 H3 0.884(16) . ? N1 H2 0.914(18) . ? C6 C5 1.3871(16) . ? C6 H5 0.949(14) . ? C5 H4 0.961(14) . ? C9 C8 1.3882(16) . ? C9 H7 0.952(14) . ? C8 H6 0.953(14) . ? C2 C1 1.5026(15) . ? C1 C1 1.509(2) 5_686 ? C1 H9 0.984(16) . ? C1 H8 0.986(16) . ? 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 O4 H1 110.7(11) . . ? C6 C7 C8 123.12(10) . . ? C6 C7 N2 118.14(10) . . ? C8 C7 N2 118.74(10) . . ? C9 C4 C5 119.79(10) . . ? C9 C4 C3 117.54(9) . . ? C5 C4 C3 122.67(10) . . ? C3 N1 H3 123.3(10) . . ? C3 N1 H2 117.0(10) . . ? H3 N1 H2 119.6(14) . . ? O1 N2 O2 124.49(10) . . ? O1 N2 C7 117.51(9) . . ? O2 N2 C7 118.01(9) . . ? C7 C6 C5 118.20(10) . . ? C7 C6 H5 120.3(9) . . ? C5 C6 H5 121.5(9) . . ? C6 C5 C4 120.34(10) . . ? C6 C5 H4 117.5(8) . . ? C4 C5 H4 122.1(8) . . ? C8 C9 C4 120.53(10) . . ? C8 C9 H7 120.8(9) . . ? C4 C9 H7 118.6(9) . . ? O3 C3 N1 121.90(10) . . ? O3 C3 C4 119.12(10) . . ? N1 C3 C4 118.98(10) . . ? C7 C8 C9 118.00(10) . . ? C7 C8 H6 120.9(9) . . ? C9 C8 H6 121.1(9) . . ? O5 C2 O4 123.07(11) . . ? O5 C2 C1 123.94(10) . . ? O4 C2 C1 112.98(9) . . ? C2 C1 C1 111.80(12) . 5_686 ? C2 C1 H9 109.6(9) . . ? C1 C1 H9 111.2(10) 5_686 . ? C2 C1 H8 107.7(9) . . ? C1 C1 H8 110.5(9) 5_686 . ? H9 C1 H8 105.8(12) . . ? 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 C6 C7 N2 O1 163.51(10) . . . . ? C8 C7 N2 O1 -16.75(15) . . . . ? C6 C7 N2 O2 -16.57(15) . . . . ? C8 C7 N2 O2 163.18(10) . . . . ? C8 C7 C6 C5 0.22(17) . . . . ? N2 C7 C6 C5 179.95(10) . . . . ? C7 C6 C5 C4 -0.99(16) . . . . ? C9 C4 C5 C6 0.75(17) . . . . ? C3 C4 C5 C6 -179.23(10) . . . . ? C5 C4 C9 C8 0.27(17) . . . . ? C3 C4 C9 C8 -179.74(10) . . . . ? C9 C4 C3 O3 -5.23(16) . . . . ? C5 C4 C3 O3 174.76(10) . . . . ? C9 C4 C3 N1 175.02(10) . . . . ? C5 C4 C3 N1 -4.99(16) . . . . ? C6 C7 C8 C9 0.78(17) . . . . ? N2 C7 C8 C9 -178.96(10) . . . . ? C4 C9 C8 C7 -1.01(17) . . . . ? O5 C2 C1 C1 -4.5(2) . . . 5_686 ? O4 C2 C1 C1 176.27(13) . . . 5_686 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.297 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 940331' ####################################################################### # # 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_platon _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,5-dinitrobenzamide: 1,4-diiodobenzene' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 I2 N6 O10' _chemical_formula_weight 752.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' I I -0.4740 1.8120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 '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 9.5268(13) _cell_length_b 9.6155(13) _cell_length_c 13.8866(19) _cell_angle_alpha 81.082(6) _cell_angle_beta 70.278(5) _cell_angle_gamma 88.850(6) _cell_volume 1182.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8053 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.113 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 2.731 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.6112 _exptl_absorpt_correction_T_max 0.7719 #=============================================================================== # 7. EXPERIMENTAL DATA _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9083 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0609 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5321 _reflns_number_gt 4435 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0650P)^2^+3.4393P] 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 5321 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1502 _refine_ls_wR_factor_gt 0.1440 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 O2 O 0.1710(4) 0.6595(4) 0.0980(3) 0.0209(8) Uani 1 1 d . . . O3 O 0.2988(5) 1.1655(4) 0.0623(3) 0.0291(9) Uani 1 1 d . . . O4 O 0.4772(5) 1.2253(4) 0.1140(3) 0.0314(10) Uani 1 1 d . . . O5 O 0.6655(5) 0.8864(5) 0.3251(3) 0.0286(10) Uani 1 1 d . . . O6 O 0.6247(5) 0.6644(4) 0.3335(3) 0.0287(9) Uani 1 1 d . . . N3 N 0.3910(5) 1.1378(5) 0.1058(4) 0.0216(10) Uani 1 1 d . . . N4 N 0.6058(5) 0.7886(5) 0.3063(3) 0.0155(9) Uani 1 1 d . . . N11 N 0.3571(5) 0.5152(4) 0.1071(4) 0.0184(9) Uani 1 1 d . . . H11A H 0.3230 0.4484 0.0833 0.022 Uiso 1 1 calc R . . H11B H 0.4387 0.5029 0.1232 0.022 Uiso 1 1 calc R . . C14 C 0.4883(6) 0.9622(5) 0.2123(4) 0.0165(10) Uani 1 1 d . . . H5 H 0.5338 1.0353 0.2316 0.020 Uiso 1 1 calc R . . C11 C 0.4019(6) 0.9902(5) 0.1501(4) 0.0175(10) Uani 1 1 d . . . C8 C 0.4414(5) 0.7127(5) 0.2187(4) 0.0139(10) Uani 1 1 d . . . H6 H 0.4566 0.6174 0.2426 0.017 Uiso 1 1 calc R . . C12 C 0.2851(5) 0.6351(5) 0.1188(4) 0.0167(10) Uani 1 1 d . . . C10 C 0.3316(5) 0.8849(5) 0.1229(4) 0.0143(10) Uani 1 1 d . . . H7 H 0.2695 0.9083 0.0822 0.017 Uiso 1 1 calc R . . C9 C 0.3537(5) 0.7456(5) 0.1561(4) 0.0159(10) Uani 1 1 d . . . C13 C 0.5052(5) 0.8212(5) 0.2451(4) 0.0135(10) Uani 1 1 d . . . O7 O 1.1280(5) 0.4154(4) 0.3338(3) 0.0260(9) Uani 1 1 d . . . O8 O 1.1866(5) 0.2007(4) 0.3199(3) 0.0293(10) Uani 1 1 d . . . O9 O 0.9716(5) -0.0637(4) 0.1395(3) 0.0303(10) Uani 1 1 d . . . O10 O 0.6707(4) 0.5214(4) 0.0995(3) 0.0211(8) Uani 1 1 d . . . O11 O 0.7982(5) 0.0215(4) 0.0814(3) 0.0277(9) Uani 1 1 d . . . N1 N 0.8895(5) 0.0302(5) 0.1250(4) 0.0197(10) Uani 1 1 d . . . N2 N 1.1162(5) 0.3047(5) 0.3048(3) 0.0161(9) Uani 1 1 d . . . N10 N 0.8583(5) 0.6595(4) 0.1011(4) 0.0204(10) Uani 1 1 d . . . H10A H 0.8224 0.7366 0.0764 0.024 Uiso 1 1 calc R . . H10B H 0.9414 0.6641 0.1151 0.024 Uiso 1 1 calc R . . C1 C 0.7869(5) 0.5359(5) 0.1173(4) 0.0158(10) Uani 1 1 d . . . C5 C 0.9950(5) 0.1676(5) 0.2185(4) 0.0153(10) Uani 1 1 d . . . H8 H 1.0421 0.0856 0.2384 0.018 Uiso 1 1 calc R . . C2 C 0.8578(5) 0.4077(5) 0.1582(4) 0.0128(9) Uani 1 1 d . . . C7 C 0.8341(5) 0.2809(5) 0.1298(4) 0.0155(10) Uani 1 1 d . . . H9 H 0.7711 0.2741 0.0903 0.019 Uiso 1 1 calc R . . C3 C 0.9487(5) 0.4177(5) 0.2172(4) 0.0153(10) Uani 1 1 d . . . H10 H 0.9650 0.5047 0.2368 0.018 Uiso 1 1 calc R . . C6 C 0.9046(5) 0.1647(5) 0.1607(4) 0.0152(10) Uani 1 1 d . . . C4 C 1.0147(5) 0.2957(5) 0.2465(4) 0.0133(10) Uani 1 1 d . . . I1 I -0.02744(4) 0.77741(3) 0.38837(3) 0.01940(13) Uani 1 1 d . . . I2 I 0.52533(4) 0.72860(3) 0.61425(3) 0.01927(13) Uani 1 1 d . . . C18 C 0.1394(6) 0.7614(5) 0.4555(4) 0.0157(10) Uani 1 1 d . . . C19 C 0.1952(6) 0.6321(5) 0.4802(4) 0.0180(11) Uani 1 1 d . . . H1 H 0.1587 0.5496 0.4653 0.022 Uiso 1 1 calc R . . C20 C 0.3041(6) 0.6218(6) 0.5264(4) 0.0169(10) Uani 1 1 d . . . H2 H 0.3419 0.5327 0.5434 0.020 Uiso 1 1 calc R . . C17 C 0.1936(6) 0.8831(5) 0.4771(4) 0.0180(11) Uani 1 1 d . . . H3 H 0.1561 0.9723 0.4598 0.022 Uiso 1 1 calc R . . C15 C 0.3574(6) 0.7426(5) 0.5476(4) 0.0154(10) Uani 1 1 d . . . C16 C 0.3017(6) 0.8733(5) 0.5237(4) 0.0175(10) Uani 1 1 d . . . H4 H 0.3377 0.9555 0.5393 0.021 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0158(18) 0.0215(18) 0.0255(19) -0.0074(15) -0.0058(15) 0.0031(14) O3 0.028(2) 0.023(2) 0.035(2) 0.0018(17) -0.0124(19) 0.0065(17) O4 0.036(2) 0.0131(18) 0.048(3) -0.0074(18) -0.017(2) -0.0022(16) O5 0.032(2) 0.032(2) 0.028(2) -0.0085(18) -0.0169(19) -0.0059(18) O6 0.040(2) 0.023(2) 0.030(2) -0.0050(17) -0.020(2) 0.0098(18) N3 0.019(2) 0.016(2) 0.023(2) -0.0062(18) 0.0032(19) 0.0005(18) N4 0.019(2) 0.018(2) 0.0092(18) 0.0003(16) -0.0050(16) 0.0010(17) N11 0.019(2) 0.013(2) 0.025(2) -0.0085(18) -0.0082(18) -0.0006(17) C14 0.017(2) 0.018(2) 0.016(2) -0.0103(19) -0.0043(19) 0.0016(19) C11 0.017(2) 0.014(2) 0.020(2) -0.0088(19) -0.001(2) 0.0046(19) C8 0.015(2) 0.012(2) 0.011(2) -0.0013(17) -0.0006(18) 0.0023(18) C12 0.014(2) 0.015(2) 0.016(2) -0.0024(18) 0.0025(19) -0.0002(18) C10 0.010(2) 0.019(2) 0.016(2) -0.0056(19) -0.0062(18) 0.0049(18) C9 0.008(2) 0.017(2) 0.020(2) -0.008(2) 0.0006(19) 0.0027(18) C13 0.010(2) 0.019(2) 0.011(2) -0.0037(19) -0.0029(18) 0.0026(18) O7 0.033(2) 0.027(2) 0.024(2) -0.0088(17) -0.0151(18) -0.0029(17) O8 0.030(2) 0.031(2) 0.035(2) -0.0076(18) -0.0210(19) 0.0113(18) O9 0.030(2) 0.0186(19) 0.047(3) -0.0155(18) -0.014(2) 0.0064(16) O10 0.0166(18) 0.0227(19) 0.030(2) -0.0106(16) -0.0127(16) 0.0036(14) O11 0.034(2) 0.026(2) 0.030(2) -0.0138(17) -0.0153(19) -0.0021(17) N1 0.019(2) 0.017(2) 0.021(2) -0.0094(18) -0.0005(18) -0.0010(17) N2 0.017(2) 0.017(2) 0.0132(19) 0.0005(17) -0.0052(17) -0.0002(17) N10 0.019(2) 0.011(2) 0.029(2) -0.0007(18) -0.0057(19) -0.0019(17) C1 0.012(2) 0.018(2) 0.018(2) -0.0095(19) -0.0029(19) 0.0031(18) C5 0.013(2) 0.016(2) 0.015(2) -0.0038(18) -0.0013(18) -0.0010(18) C2 0.008(2) 0.016(2) 0.012(2) -0.0032(18) -0.0004(17) 0.0008(17) C7 0.011(2) 0.018(2) 0.017(2) -0.0085(19) -0.0007(18) -0.0032(18) C3 0.013(2) 0.013(2) 0.019(2) -0.0071(19) -0.0029(19) 0.0017(18) C6 0.015(2) 0.012(2) 0.017(2) -0.0081(18) -0.0014(19) -0.0023(18) C4 0.009(2) 0.020(2) 0.011(2) -0.0034(19) -0.0036(18) -0.0010(18) I1 0.0199(2) 0.0200(2) 0.0215(2) -0.00443(15) -0.01067(15) 0.00309(14) I2 0.0178(2) 0.0217(2) 0.0216(2) -0.00664(15) -0.00953(15) 0.00067(14) C18 0.013(2) 0.016(2) 0.013(2) -0.0034(19) 0.0021(19) -0.0003(19) C19 0.020(3) 0.010(2) 0.022(3) -0.003(2) -0.005(2) -0.0026(19) C20 0.017(2) 0.018(2) 0.018(2) -0.006(2) -0.008(2) 0.0055(19) C17 0.020(3) 0.009(2) 0.025(3) -0.004(2) -0.008(2) 0.0036(19) C15 0.014(2) 0.014(2) 0.015(2) -0.0046(19) 0.0011(19) -0.0009(19) C16 0.021(3) 0.010(2) 0.023(3) -0.004(2) -0.008(2) 0.0007(19) _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 O2 C12 1.225(6) . ? O3 N3 1.227(6) . ? O4 N3 1.231(6) . ? O5 N4 1.214(6) . ? O6 N4 1.224(6) . ? N3 C11 1.474(7) . ? N4 C13 1.481(7) . ? N11 C12 1.333(6) . ? N11 H11A 0.8800 . ? N11 H11B 0.8800 . ? C14 C11 1.377(8) . ? C14 C13 1.386(7) . ? C14 H5 0.9500 . ? C11 C10 1.390(7) . ? C8 C13 1.374(7) . ? C8 C9 1.396(8) . ? C8 H6 0.9500 . ? C12 C9 1.500(7) . ? C10 C9 1.383(7) . ? C10 H7 0.9500 . ? O7 N2 1.215(6) . ? O8 N2 1.223(6) . ? O9 N1 1.220(6) . ? O10 C1 1.228(6) . ? O11 N1 1.226(6) . ? N1 C6 1.481(6) . ? N2 C4 1.467(7) . ? N10 C1 1.331(6) . ? N10 H10A 0.8800 . ? N10 H10B 0.8800 . ? C1 C2 1.519(7) . ? C5 C6 1.364(7) . ? C5 C4 1.383(7) . ? C5 H8 0.9500 . ? C2 C7 1.382(7) . ? C2 C3 1.393(7) . ? C7 C6 1.377(7) . ? C7 H9 0.9500 . ? C3 C4 1.389(7) . ? C3 H10 0.9500 . ? I1 C18 2.089(6) . ? I2 C15 2.094(6) . ? C18 C19 1.382(7) . ? C18 C17 1.402(7) . ? C19 C20 1.387(8) . ? C19 H1 0.9500 . ? C20 C15 1.388(7) . ? C20 H2 0.9500 . ? C17 C16 1.383(8) . ? C17 H3 0.9500 . ? C15 C16 1.391(7) . ? C16 H4 0.9500 . ? 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 O3 N3 O4 124.4(5) . . ? O3 N3 C11 118.4(4) . . ? O4 N3 C11 117.2(5) . . ? O5 N4 O6 124.3(5) . . ? O5 N4 C13 118.0(4) . . ? O6 N4 C13 117.7(4) . . ? C12 N11 H11A 120.0 . . ? C12 N11 H11B 120.0 . . ? H11A N11 H11B 120.0 . . ? C11 C14 C13 116.2(5) . . ? C11 C14 H5 121.9 . . ? C13 C14 H5 121.9 . . ? C14 C11 C10 122.8(5) . . ? C14 C11 N3 118.3(5) . . ? C10 C11 N3 118.8(5) . . ? C13 C8 C9 118.5(4) . . ? C13 C8 H6 120.8 . . ? C9 C8 H6 120.8 . . ? O2 C12 N11 123.6(5) . . ? O2 C12 C9 119.8(4) . . ? N11 C12 C9 116.7(5) . . ? C9 C10 C11 119.0(5) . . ? C9 C10 H7 120.5 . . ? C11 C10 H7 120.5 . . ? C10 C9 C8 120.0(5) . . ? C10 C9 C12 117.4(5) . . ? C8 C9 C12 122.6(4) . . ? C8 C13 C14 123.6(5) . . ? C8 C13 N4 119.3(5) . . ? C14 C13 N4 117.0(5) . . ? O9 N1 O11 124.5(5) . . ? O9 N1 C6 117.2(5) . . ? O11 N1 C6 118.2(4) . . ? O7 N2 O8 123.6(5) . . ? O7 N2 C4 118.4(4) . . ? O8 N2 C4 118.0(4) . . ? C1 N10 H10A 120.0 . . ? C1 N10 H10B 120.0 . . ? H10A N10 H10B 120.0 . . ? O10 C1 N10 123.6(5) . . ? O10 C1 C2 119.7(4) . . ? N10 C1 C2 116.7(5) . . ? C6 C5 C4 116.8(5) . . ? C6 C5 H8 121.6 . . ? C4 C5 H8 121.6 . . ? C7 C2 C3 121.1(5) . . ? C7 C2 C1 117.0(5) . . ? C3 C2 C1 121.8(4) . . ? C6 C7 C2 118.1(5) . . ? C6 C7 H9 121.0 . . ? C2 C7 H9 121.0 . . ? C4 C3 C2 117.6(5) . . ? C4 C3 H10 121.2 . . ? C2 C3 H10 121.2 . . ? C5 C6 C7 123.7(5) . . ? C5 C6 N1 117.3(4) . . ? C7 C6 N1 119.0(5) . . ? C5 C4 C3 122.8(5) . . ? C5 C4 N2 118.4(5) . . ? C3 C4 N2 118.7(5) . . ? C19 C18 C17 119.7(5) . . ? C19 C18 I1 120.8(4) . . ? C17 C18 I1 119.5(4) . . ? C18 C19 C20 120.6(5) . . ? C18 C19 H1 119.7 . . ? C20 C19 H1 119.7 . . ? C19 C20 C15 119.5(5) . . ? C19 C20 H2 120.2 . . ? C15 C20 H2 120.2 . . ? C16 C17 C18 120.0(5) . . ? C16 C17 H3 120.0 . . ? C18 C17 H3 120.0 . . ? C20 C15 C16 120.6(5) . . ? C20 C15 I2 119.8(4) . . ? C16 C15 I2 119.7(4) . . ? C17 C16 C15 119.7(5) . . ? C17 C16 H4 120.2 . . ? C15 C16 H4 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 C14 C11 C10 1.5(7) . . . . ? C13 C14 C11 N3 -174.8(4) . . . . ? O3 N3 C11 C14 -170.2(4) . . . . ? O4 N3 C11 C14 10.7(7) . . . . ? O3 N3 C11 C10 13.3(7) . . . . ? O4 N3 C11 C10 -165.8(4) . . . . ? C14 C11 C10 C9 -2.6(7) . . . . ? N3 C11 C10 C9 173.7(4) . . . . ? C11 C10 C9 C8 2.1(7) . . . . ? C11 C10 C9 C12 -175.7(4) . . . . ? C13 C8 C9 C10 -0.6(7) . . . . ? C13 C8 C9 C12 177.0(4) . . . . ? O2 C12 C9 C10 -28.7(7) . . . . ? N11 C12 C9 C10 149.1(5) . . . . ? O2 C12 C9 C8 153.6(5) . . . . ? N11 C12 C9 C8 -28.6(7) . . . . ? C9 C8 C13 C14 -0.5(7) . . . . ? C9 C8 C13 N4 -176.4(4) . . . . ? C11 C14 C13 C8 0.1(7) . . . . ? C11 C14 C13 N4 176.1(4) . . . . ? O5 N4 C13 C8 177.1(4) . . . . ? O6 N4 C13 C8 -1.9(7) . . . . ? O5 N4 C13 C14 0.9(6) . . . . ? O6 N4 C13 C14 -178.1(4) . . . . ? O10 C1 C2 C7 29.4(6) . . . . ? N10 C1 C2 C7 -149.6(5) . . . . ? O10 C1 C2 C3 -153.8(5) . . . . ? N10 C1 C2 C3 27.2(6) . . . . ? C3 C2 C7 C6 -0.8(7) . . . . ? C1 C2 C7 C6 176.1(4) . . . . ? C7 C2 C3 C4 0.0(7) . . . . ? C1 C2 C3 C4 -176.7(4) . . . . ? C4 C5 C6 C7 0.1(7) . . . . ? C4 C5 C6 N1 176.6(4) . . . . ? C2 C7 C6 C5 0.7(7) . . . . ? C2 C7 C6 N1 -175.7(4) . . . . ? O9 N1 C6 C5 -8.2(6) . . . . ? O11 N1 C6 C5 173.2(4) . . . . ? O9 N1 C6 C7 168.5(5) . . . . ? O11 N1 C6 C7 -10.1(7) . . . . ? C6 C5 C4 C3 -0.9(7) . . . . ? C6 C5 C4 N2 -177.4(4) . . . . ? C2 C3 C4 C5 0.8(7) . . . . ? C2 C3 C4 N2 177.3(4) . . . . ? O7 N2 C4 C5 -176.5(4) . . . . ? O8 N2 C4 C5 4.9(7) . . . . ? O7 N2 C4 C3 6.8(7) . . . . ? O8 N2 C4 C3 -171.8(5) . . . . ? C17 C18 C19 C20 0.2(8) . . . . ? I1 C18 C19 C20 -178.9(4) . . . . ? C18 C19 C20 C15 -0.2(8) . . . . ? C19 C18 C17 C16 -0.5(8) . . . . ? I1 C18 C17 C16 178.5(4) . . . . ? C19 C20 C15 C16 0.5(8) . . . . ? C19 C20 C15 I2 -178.6(4) . . . . ? C18 C17 C16 C15 0.8(8) . . . . ? C20 C15 C16 C17 -0.9(8) . . . . ? I2 C15 C16 C17 178.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.723 _refine_diff_density_min -2.250 _refine_diff_density_rms 0.199 _database_code_depnum_ccdc_archive 'CCDC 940332' ####################################################################### # # 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_platon _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-nitrobenzamide:1,4-dioxane solvate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 N2 O4' _chemical_formula_weight 210.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 '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 6.9143(9) _cell_length_b 7.4292(10) _cell_length_c 10.0061(13) _cell_angle_alpha 94.403(7) _cell_angle_beta 95.082(7) _cell_angle_gamma 111.305(8) _cell_volume 473.68(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4747 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour 'colour less' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.118 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9655 _exptl_absorpt_correction_T_max 0.9768 #=============================================================================== # 7. EXPERIMENTAL DATA _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 ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4979 _diffrn_reflns_av_R_equivalents 0.0132 _diffrn_reflns_av_sigmaI/netI 0.0152 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2149 _reflns_number_gt 1971 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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^)+(0.0539P)^2^+0.2169P] 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_number_reflns 2149 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.41567(14) 0.87494(14) 0.33465(9) 0.0294(2) Uani 1 1 d . . . O2 O 0.64196(19) 0.59914(18) -0.20356(11) 0.0456(3) Uani 1 1 d . . . O3 O 0.45329(18) 0.7099(2) -0.08918(12) 0.0551(4) Uani 1 1 d . . . N1 N 0.61349(18) 0.68191(17) -0.10138(11) 0.0286(3) Uani 1 1 d . . . N2 N 1.28614(16) 1.08286(15) 0.43365(10) 0.0237(2) Uani 1 1 d . . . H1 H 1.1929 1.1370 0.4303 0.028 Uiso 1 1 d R . . H2 H 1.3890 1.1125 0.5046 0.028 Uiso 1 1 d R . . C1 C 0.91229(19) 0.90390(19) 0.23780(12) 0.0246(3) Uani 1 1 d . . . H3 H 0.8940 0.9651 0.3200 0.029 Uiso 1 1 calc R . . C2 C 1.28065(18) 0.94744(17) 0.33645(12) 0.0210(3) Uani 1 1 d . . . C3 C 0.78261(19) 0.75136(17) 0.01307(12) 0.0225(3) Uani 1 1 d . . . C4 C 1.10108(18) 0.88177(16) 0.22445(11) 0.0195(2) Uani 1 1 d . . . C5 C 0.9673(2) 0.7264(2) -0.00318(13) 0.0276(3) Uani 1 1 d . . . H7 H 0.9853 0.6664 -0.0860 0.033 Uiso 1 1 calc R . . C6 C 1.1265(2) 0.7909(2) 0.10411(13) 0.0287(3) Uani 1 1 d . . . H6 H 1.2542 0.7730 0.0954 0.034 Uiso 1 1 calc R . . C7 C 0.7502(2) 0.8373(2) 0.13203(13) 0.0284(3) Uani 1 1 d . . . H8 H 0.6202 0.8505 0.1412 0.034 Uiso 1 1 calc R . . O4 O 0.03259(14) 0.32366(13) 0.47435(9) 0.0267(2) Uani 1 1 d . . . C8 C 0.2009(2) 0.50051(18) 0.53136(14) 0.0274(3) Uani 1 1 d . . . H4 H 0.2736 0.5681 0.4581 0.033 Uiso 1 1 calc R . . H9 H 0.3034 0.4696 0.5915 0.033 Uiso 1 1 calc R . . C9 C -0.1184(2) 0.3685(2) 0.38950(14) 0.0295(3) Uani 1 1 d . . . H5 H -0.2356 0.2466 0.3517 0.035 Uiso 1 1 calc R . . H10 H -0.0525 0.4335 0.3133 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0274(5) 0.0408(5) 0.0249(5) -0.0042(4) -0.0031(4) 0.0216(4) O2 0.0462(6) 0.0591(7) 0.0263(5) -0.0146(5) -0.0079(5) 0.0200(6) O3 0.0311(6) 0.0965(11) 0.0366(6) -0.0146(6) -0.0107(5) 0.0302(6) N1 0.0256(5) 0.0323(6) 0.0226(5) 0.0009(4) -0.0022(4) 0.0062(5) N2 0.0232(5) 0.0256(5) 0.0227(5) -0.0030(4) -0.0041(4) 0.0125(4) C1 0.0232(6) 0.0324(7) 0.0188(6) -0.0021(5) 0.0017(4) 0.0125(5) C2 0.0208(5) 0.0231(6) 0.0200(6) 0.0038(4) 0.0021(4) 0.0090(4) C3 0.0217(6) 0.0233(6) 0.0189(6) 0.0022(4) -0.0010(4) 0.0051(5) C4 0.0213(6) 0.0195(5) 0.0186(5) 0.0032(4) 0.0013(4) 0.0087(4) C5 0.0298(7) 0.0336(7) 0.0201(6) -0.0042(5) 0.0018(5) 0.0144(5) C6 0.0259(6) 0.0384(7) 0.0256(6) -0.0044(5) 0.0009(5) 0.0184(6) C7 0.0206(6) 0.0397(7) 0.0251(6) -0.0023(5) 0.0011(5) 0.0132(5) O4 0.0248(5) 0.0211(4) 0.0335(5) -0.0035(3) -0.0039(4) 0.0109(4) C8 0.0216(6) 0.0237(6) 0.0353(7) -0.0029(5) -0.0034(5) 0.0095(5) C9 0.0296(6) 0.0284(6) 0.0293(7) -0.0066(5) -0.0075(5) 0.0141(5) _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 O1 C2 1.2365(15) . ? O2 N1 1.2204(15) . ? O3 N1 1.2136(16) . ? N1 C3 1.4760(15) . ? N2 C2 1.3322(15) . ? N2 H1 0.8748 . ? N2 H2 0.9115 . ? C1 C7 1.3885(17) . ? C1 C4 1.3900(16) . ? C1 H3 0.9500 . ? C2 C4 1.5050(16) . ? C3 C5 1.3772(18) . ? C3 C7 1.3818(17) . ? C4 C6 1.3913(17) . ? C5 C6 1.3864(18) . ? C5 H7 0.9500 . ? C6 H6 0.9500 . ? C7 H8 0.9500 . ? O4 C8 1.4361(15) . ? O4 C9 1.4356(15) . ? C8 C9 1.5050(18) 2_566 ? C8 H4 0.9900 . ? C8 H9 0.9900 . ? C9 C8 1.5050(18) 2_566 ? C9 H5 0.9900 . ? C9 H10 0.9900 . ? 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 O3 N1 O2 123.32(12) . . ? O3 N1 C3 118.41(11) . . ? O2 N1 C3 118.27(11) . . ? C2 N2 H1 121.3 . . ? C2 N2 H2 116.4 . . ? H1 N2 H2 122.2 . . ? C7 C1 C4 120.59(11) . . ? C7 C1 H3 119.7 . . ? C4 C1 H3 119.7 . . ? O1 C2 N2 122.97(11) . . ? O1 C2 C4 119.27(11) . . ? N2 C2 C4 117.75(10) . . ? C5 C3 C7 122.51(11) . . ? C5 C3 N1 118.22(11) . . ? C7 C3 N1 119.27(11) . . ? C6 C4 C1 119.47(11) . . ? C6 C4 C2 117.56(11) . . ? C1 C4 C2 122.95(11) . . ? C3 C5 C6 118.46(12) . . ? C3 C5 H7 120.8 . . ? C6 C5 H7 120.8 . . ? C5 C6 C4 120.63(12) . . ? C5 C6 H6 119.7 . . ? C4 C6 H6 119.7 . . ? C3 C7 C1 118.32(11) . . ? C3 C7 H8 120.8 . . ? C1 C7 H8 120.8 . . ? C8 O4 C9 109.64(9) . . ? O4 C8 C9 110.35(11) . 2_566 ? O4 C8 H4 109.6 . . ? C9 C8 H4 109.6 2_566 . ? O4 C8 H9 109.6 . . ? C9 C8 H9 109.6 2_566 . ? H4 C8 H9 108.1 . . ? O4 C9 C8 110.58(11) . 2_566 ? O4 C9 H5 109.5 . . ? C8 C9 H5 109.5 2_566 . ? O4 C9 H10 109.5 . . ? C8 C9 H10 109.5 2_566 . ? H5 C9 H10 108.1 . . ? 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 O3 N1 C3 C5 -177.38(13) . . . . ? O2 N1 C3 C5 2.62(18) . . . . ? O3 N1 C3 C7 3.01(19) . . . . ? O2 N1 C3 C7 -176.98(13) . . . . ? C7 C1 C4 C6 -0.4(2) . . . . ? C7 C1 C4 C2 -178.76(12) . . . . ? O1 C2 C4 C6 -19.84(17) . . . . ? N2 C2 C4 C6 160.04(12) . . . . ? O1 C2 C4 C1 158.56(12) . . . . ? N2 C2 C4 C1 -21.56(17) . . . . ? C7 C3 C5 C6 -0.3(2) . . . . ? N1 C3 C5 C6 -179.85(12) . . . . ? C3 C5 C6 C4 -1.1(2) . . . . ? C1 C4 C6 C5 1.4(2) . . . . ? C2 C4 C6 C5 179.87(12) . . . . ? C5 C3 C7 C1 1.2(2) . . . . ? N1 C3 C7 C1 -179.17(12) . . . . ? C4 C1 C7 C3 -0.9(2) . . . . ? C9 O4 C8 C9 57.97(15) . . . 2_566 ? C8 O4 C9 C8 -58.11(16) . . . 2_566 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.325 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 940333'