# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; Dr. Guoping Yong Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China, ; _publ_contact_author_email gpyong@ustc.edu.cn _publ_contact_author_name 'Dr. Guoping Yong' loop_ _publ_author_name 'Guoping Yong' 'Yiman Zhang' 'Wenlong She' #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 821840' #TrackingRef '- Compd1-3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 Cl N2 O8' _chemical_formula_weight 308.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.3426(2) _cell_length_b 9.4653(2) _cell_length_c 11.4987(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.212(2) _cell_angle_gamma 90.00 _cell_volume 1206.58(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3964 _cell_measurement_temperature 150(2) _cell_measurement_theta_min 3.9305 _cell_measurement_theta_max 67.5459 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 3.241 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.358 _exptl_absorpt_correction_T_max 0.378 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4786 _diffrn_reflns_av_R_equivalents 0.0156 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.98 _diffrn_reflns_theta_max 67.65 _reflns_number_total 2124 _reflns_number_gt 2057 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1193P)^2^+5.0470P] 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 2124 _refine_ls_number_parameters 185 _refine_ls_number_restraints 22 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0832 _refine_ls_wR_factor_ref 0.2133 _refine_ls_wR_factor_gt 0.2127 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.068 _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 N1 N 0.6036(3) 0.0753(4) 0.8000(3) 0.0216(8) Uani 1 1 d . . . O2 O 0.6305(3) 0.5374(3) 0.6416(3) 0.0300(8) Uani 1 1 d . . . H2 H 0.5956 0.6114 0.6190 0.045 Uiso 1 1 calc R . . N2 N 0.4234(3) 0.0706(4) 0.8392(3) 0.0193(7) Uani 1 1 d . . . O1 O 0.7318(3) 0.3058(3) 0.7409(3) 0.0316(8) Uani 1 1 d . . . C6 C 0.4431(4) 0.2070(4) 0.8049(3) 0.0199(8) Uani 1 1 d . . . H6A H 0.3899 0.2827 0.7997 0.024 Uiso 1 1 calc R . . C9 C 0.5595(4) 0.4564(4) 0.6886(4) 0.0225(9) Uani 1 1 d . . . C7 C 0.5551(3) 0.2093(4) 0.7804(3) 0.0189(8) Uani 1 1 d . . . C5 C 0.3222(4) 0.0117(5) 0.8705(4) 0.0240(9) Uani 1 1 d . . . H5A H 0.2548 0.0667 0.8730 0.029 Uiso 1 1 calc R . . C4 C 0.3241(4) -0.1263(5) 0.8970(4) 0.0257(9) Uani 1 1 d . . . H4A H 0.2572 -0.1669 0.9184 0.031 Uiso 1 1 calc R . . C8 C 0.6261(4) 0.3214(4) 0.7386(4) 0.0215(9) Uani 1 1 d . . . C3 C 0.4261(4) -0.2119(5) 0.8929(4) 0.0258(9) Uani 1 1 d . . . H3A H 0.4252 -0.3074 0.9117 0.031 Uiso 1 1 calc R . . C2 C 0.5255(4) -0.1547(4) 0.8616(4) 0.0249(9) Uani 1 1 d . . . H2A H 0.5929 -0.2095 0.8586 0.030 Uiso 1 1 calc R . . C1 C 0.5221(3) -0.0101(4) 0.8341(3) 0.0191(8) Uani 1 1 d . . . O3 O 0.4564(3) 0.4801(3) 0.6936(3) 0.0327(8) Uani 1 1 d . . . Cl1 Cl 0.25917(9) -0.04252(10) 0.51297(9) 0.0247(4) Uani 1 1 d D . . O8 O 0.4788(4) 0.2531(4) 0.4715(4) 0.0400(9) Uani 1 1 d . . . O6 O 0.2839(5) 0.0665(5) 0.5983(5) 0.078(2) Uani 0.906(12) 1 d PDU A 1 O7 O 0.3431(4) -0.0172(6) 0.4347(5) 0.0602(17) Uani 0.906(12) 1 d PDU A 1 H4 H 0.533(7) 0.219(9) 0.439(7) 0.07(2) Uiso 1 1 d . . . H3 H 0.447(6) 0.181(8) 0.460(6) 0.045(19) Uiso 1 1 d . . . O5 O 0.1398(4) -0.0291(5) 0.4430(4) 0.0612(12) Uiso 1 1 d D A . O4 O 0.2840(4) -0.1790(4) 0.5644(4) 0.0575(11) Uiso 1 1 d D A . H1 H 0.678(6) 0.050(7) 0.798(6) 0.050(18) Uiso 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 N1 0.0174(17) 0.0224(18) 0.0270(18) 0.0044(14) 0.0094(14) 0.0029(14) O2 0.0219(15) 0.0229(16) 0.047(2) 0.0123(13) 0.0114(14) 0.0006(12) N2 0.0173(16) 0.0214(17) 0.0200(17) -0.0002(13) 0.0055(13) -0.0005(13) O1 0.0199(15) 0.0269(16) 0.051(2) 0.0112(14) 0.0139(14) 0.0018(12) C6 0.0206(19) 0.0179(19) 0.0213(19) 0.0002(15) 0.0049(15) 0.0010(15) C9 0.022(2) 0.020(2) 0.025(2) 0.0000(16) 0.0030(16) -0.0029(15) C7 0.0202(19) 0.0181(19) 0.0187(18) 0.0013(15) 0.0043(15) -0.0013(15) C5 0.0175(19) 0.028(2) 0.028(2) -0.0007(18) 0.0097(16) -0.0032(17) C4 0.023(2) 0.029(2) 0.027(2) -0.0010(17) 0.0094(17) -0.0084(17) C8 0.0203(19) 0.022(2) 0.023(2) -0.0005(16) 0.0061(15) -0.0011(16) C3 0.030(2) 0.021(2) 0.025(2) 0.0017(17) 0.0047(17) -0.0020(17) C2 0.025(2) 0.020(2) 0.031(2) 0.0034(17) 0.0099(17) 0.0013(16) C1 0.0175(19) 0.022(2) 0.0180(19) 0.0011(16) 0.0049(15) -0.0007(16) O3 0.0200(15) 0.0283(17) 0.051(2) 0.0092(15) 0.0109(14) 0.0037(12) Cl1 0.0268(6) 0.0209(6) 0.0258(6) -0.0034(4) 0.0043(4) 0.0014(4) O8 0.036(2) 0.0248(19) 0.062(3) 0.0120(17) 0.0171(18) 0.0062(16) O6 0.092(4) 0.053(3) 0.067(4) -0.037(3) -0.032(3) 0.023(3) O7 0.061(3) 0.065(3) 0.063(3) 0.022(3) 0.034(3) 0.018(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.347(5) . ? N1 C7 1.382(5) . ? N1 H1 0.88(7) . ? O2 C9 1.308(5) . ? O2 H2 0.8200 . ? N2 C1 1.367(5) . ? N2 C6 1.382(5) . ? N2 C5 1.390(5) . ? O1 C8 1.203(5) . ? C6 C7 1.359(5) . ? C6 H6A 0.9300 . ? C9 O3 1.204(5) . ? C9 C8 1.533(6) . ? C7 C8 1.473(5) . ? C5 C4 1.340(7) . ? C5 H5A 0.9300 . ? C4 C3 1.422(6) . ? C4 H4A 0.9300 . ? C3 C2 1.366(6) . ? C3 H3A 0.9300 . ? C2 C1 1.404(6) . ? C2 H2A 0.9300 . ? Cl1 O6 1.411(4) . ? Cl1 O4 1.424(4) . ? Cl1 O5 1.427(4) . ? Cl1 O7 1.462(4) . ? O8 H4 0.84(8) . ? O8 H3 0.77(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C7 108.9(3) . . ? C1 N1 H1 125(4) . . ? C7 N1 H1 126(4) . . ? C9 O2 H2 109.5 . . ? C1 N2 C6 109.1(3) . . ? C1 N2 C5 121.0(4) . . ? C6 N2 C5 129.9(4) . . ? C7 C6 N2 106.8(3) . . ? C7 C6 H6A 126.6 . . ? N2 C6 H6A 126.6 . . ? O3 C9 O2 126.9(4) . . ? O3 C9 C8 122.9(4) . . ? O2 C9 C8 110.2(3) . . ? C6 C7 N1 108.0(3) . . ? C6 C7 C8 132.8(4) . . ? N1 C7 C8 119.2(3) . . ? C4 C5 N2 118.4(4) . . ? C4 C5 H5A 120.8 . . ? N2 C5 H5A 120.8 . . ? C5 C4 C3 121.5(4) . . ? C5 C4 H4A 119.2 . . ? C3 C4 H4A 119.2 . . ? O1 C8 C7 121.0(4) . . ? O1 C8 C9 121.4(4) . . ? C7 C8 C9 117.6(3) . . ? C2 C3 C4 120.4(4) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C3 C2 C1 117.5(4) . . ? C3 C2 H2A 121.3 . . ? C1 C2 H2A 121.3 . . ? N1 C1 N2 107.2(4) . . ? N1 C1 C2 131.5(4) . . ? N2 C1 C2 121.3(4) . . ? O6 Cl1 O4 112.5(3) . . ? O6 Cl1 O5 110.6(3) . . ? O4 Cl1 O5 113.3(3) . . ? O6 Cl1 O7 104.4(4) . . ? O4 Cl1 O7 107.9(3) . . ? O5 Cl1 O7 107.6(3) . . ? H4 O8 H3 87(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 C1 N2 C6 C7 -0.7(4) . . . . ? C5 N2 C6 C7 -178.1(4) . . . . ? N2 C6 C7 N1 -0.3(4) . . . . ? N2 C6 C7 C8 179.0(4) . . . . ? C1 N1 C7 C6 1.2(5) . . . . ? C1 N1 C7 C8 -178.2(3) . . . . ? C1 N2 C5 C4 0.7(6) . . . . ? C6 N2 C5 C4 177.8(4) . . . . ? N2 C5 C4 C3 -0.3(6) . . . . ? C6 C7 C8 O1 167.8(4) . . . . ? N1 C7 C8 O1 -13.0(6) . . . . ? C6 C7 C8 C9 -14.0(6) . . . . ? N1 C7 C8 C9 165.2(4) . . . . ? O3 C9 C8 O1 -174.0(4) . . . . ? O2 C9 C8 O1 6.3(6) . . . . ? O3 C9 C8 C7 7.9(6) . . . . ? O2 C9 C8 C7 -171.9(4) . . . . ? C5 C4 C3 C2 0.0(7) . . . . ? C4 C3 C2 C1 0.0(6) . . . . ? C7 N1 C1 N2 -1.6(4) . . . . ? C7 N1 C1 C2 178.3(4) . . . . ? C6 N2 C1 N1 1.5(4) . . . . ? C5 N2 C1 N1 179.1(3) . . . . ? C6 N2 C1 C2 -178.4(4) . . . . ? C5 N2 C1 C2 -0.8(6) . . . . ? C3 C2 C1 N1 -179.5(4) . . . . ? C3 C2 C1 N2 0.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 67.65 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 1.435 _refine_diff_density_min -1.043 _refine_diff_density_rms 0.116 #===END data_1 _database_code_depnum_ccdc_archive 'CCDC 842574' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 Cl N2 O5' _chemical_formula_weight 276.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1069(16) _cell_length_b 9.2546(19) _cell_length_c 9.999(2) _cell_angle_alpha 64.91(3) _cell_angle_beta 74.11(3) _cell_angle_gamma 69.67(3) _cell_volume 630.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.318 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.881 _exptl_absorpt_correction_T_max 0.909 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5296 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 24.71 _reflns_number_total 2142 _reflns_number_gt 1892 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+1.7356P] 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 2142 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0775 _refine_ls_wR_factor_ref 0.1946 _refine_ls_wR_factor_gt 0.1904 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 Cl1 Cl 0.68492(16) 0.03382(16) 1.25758(13) 0.0571(4) Uani 1 1 d . . . C1 C 1.2397(6) -0.4853(5) 1.2352(4) 0.0384(9) Uani 1 1 d . . . C2 C 1.3423(7) -0.5999(6) 1.3471(5) 0.0522(12) Uani 1 1 d . . . H2A H 1.4253 -0.6948 1.3363 0.063 Uiso 1 1 calc R . . C3 C 1.3149(8) -0.5660(6) 1.4724(5) 0.0597(13) Uani 1 1 d . . . H3A H 1.3812 -0.6394 1.5489 0.072 Uiso 1 1 calc R . . C4 C 1.1887(8) -0.4226(6) 1.4895(5) 0.0591(13) Uani 1 1 d . . . H4A H 1.1724 -0.4031 1.5768 0.071 Uiso 1 1 calc R . . C5 C 1.0919(7) -0.3139(6) 1.3804(5) 0.0519(12) Uani 1 1 d . . . H5A H 1.0094 -0.2187 1.3908 0.062 Uiso 1 1 calc R . . C6 C 1.0371(6) -0.2544(5) 1.1254(4) 0.0401(10) Uani 1 1 d . . . H6A H 0.9500 -0.1541 1.1078 0.048 Uiso 1 1 calc R . . C7 C 1.1102(5) -0.3388(5) 1.0316(4) 0.0381(9) Uani 1 1 d . . . C8 C 1.0819(6) -0.3108(5) 0.8836(5) 0.0425(10) Uani 1 1 d . . . C9 C 0.9420(6) -0.1540(5) 0.8075(5) 0.0406(10) Uani 1 1 d . . . C10 C 0.4615(7) 0.2310(6) -0.1107(6) 0.0583(13) Uani 1 1 d . . . H10B H 0.4225 0.3286 -0.1944 0.087 Uiso 1 1 calc R . . H10A H 0.3837 0.1609 -0.0794 0.087 Uiso 1 1 calc R . . H10C H 0.5805 0.1726 -0.1390 0.087 Uiso 1 1 calc R . . N1 N 1.2347(5) -0.4814(4) 1.1012(4) 0.0409(8) Uani 1 1 d . . . N2 N 1.1175(5) -0.3468(4) 1.2527(4) 0.0409(8) Uani 1 1 d . . . O1 O 1.1606(5) -0.4127(4) 0.8266(4) 0.0685(11) Uani 1 1 d . . . O2 O 0.9177(5) -0.1534(4) 0.6831(4) 0.0589(9) Uani 1 1 d . . . O3 O 0.8655(4) -0.0513(4) 0.8624(4) 0.0534(9) Uani 1 1 d . . . O4 O 0.4582(6) 0.2766(5) 0.0080(5) 0.0802(13) Uani 1 1 d . . . H2 H 0.5392 0.2114 0.0555 0.120 Uiso 1 1 calc R . . O5 O 0.6753(10) 0.0609(8) 0.5664(7) 0.134(2) Uani 1 1 d . . . H1 H 1.298(7) -0.563(7) 1.065(6) 0.061(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0494(7) 0.0646(8) 0.0500(7) -0.0238(6) -0.0110(5) -0.0002(5) C1 0.047(2) 0.037(2) 0.035(2) -0.0154(17) -0.0080(18) -0.0113(18) C2 0.064(3) 0.042(2) 0.050(3) -0.017(2) -0.022(2) -0.004(2) C3 0.077(4) 0.058(3) 0.044(3) -0.016(2) -0.026(3) -0.010(3) C4 0.090(4) 0.058(3) 0.038(2) -0.023(2) -0.015(2) -0.019(3) C5 0.070(3) 0.049(3) 0.040(2) -0.024(2) -0.008(2) -0.010(2) C6 0.046(2) 0.037(2) 0.036(2) -0.0136(18) -0.0086(18) -0.0063(18) C7 0.042(2) 0.037(2) 0.036(2) -0.0142(17) -0.0089(18) -0.0073(18) C8 0.050(3) 0.040(2) 0.041(2) -0.0182(19) -0.0127(19) -0.0067(19) C9 0.040(2) 0.044(2) 0.039(2) -0.0155(19) -0.0084(18) -0.0095(19) C10 0.054(3) 0.056(3) 0.065(3) -0.033(3) -0.007(2) -0.003(2) N1 0.048(2) 0.0371(19) 0.0395(19) -0.0188(16) -0.0138(16) -0.0018(16) N2 0.053(2) 0.0377(19) 0.0337(18) -0.0150(15) -0.0095(16) -0.0091(16) O1 0.094(3) 0.054(2) 0.057(2) -0.0351(18) -0.031(2) 0.0139(19) O2 0.068(2) 0.063(2) 0.0487(19) -0.0278(16) -0.0230(16) -0.0011(17) O3 0.0497(19) 0.0524(19) 0.056(2) -0.0262(16) -0.0178(15) 0.0053(15) O4 0.101(3) 0.060(2) 0.079(3) -0.041(2) -0.053(2) 0.030(2) O5 0.182(6) 0.150(5) 0.107(4) -0.070(4) 0.023(4) -0.090(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.337(5) . ? C1 N2 1.367(5) . ? C1 C2 1.400(6) . ? C2 C3 1.360(7) . ? C2 H2A 0.9300 . ? C3 C4 1.412(7) . ? C3 H3A 0.9300 . ? C4 C5 1.344(7) . ? C4 H4A 0.9300 . ? C5 N2 1.381(5) . ? C5 H5A 0.9300 . ? C6 C7 1.356(6) . ? C6 N2 1.386(5) . ? C6 H6A 0.9300 . ? C7 N1 1.387(5) . ? C7 C8 1.460(6) . ? C8 O1 1.208(5) . ? C8 C9 1.537(6) . ? C9 O3 1.198(5) . ? C9 O2 1.309(5) . ? C10 O4 1.409(6) . ? C10 H10B 0.9600 . ? C10 H10A 0.9600 . ? C10 H10C 0.9600 . ? N1 H1 0.91(6) . ? O4 H2 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 107.3(4) . . ? N1 C1 C2 131.7(4) . . ? N2 C1 C2 121.0(4) . . ? C3 C2 C1 116.9(4) . . ? C3 C2 H2A 121.6 . . ? C1 C2 H2A 121.6 . . ? C2 C3 C4 121.8(4) . . ? C2 C3 H3A 119.1 . . ? C4 C3 H3A 119.1 . . ? C5 C4 C3 120.4(4) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C4 C5 N2 118.6(4) . . ? C4 C5 H5A 120.7 . . ? N2 C5 H5A 120.7 . . ? C7 C6 N2 106.5(4) . . ? C7 C6 H6A 126.7 . . ? N2 C6 H6A 126.7 . . ? C6 C7 N1 108.0(4) . . ? C6 C7 C8 133.9(4) . . ? N1 C7 C8 118.1(4) . . ? O1 C8 C7 120.4(4) . . ? O1 C8 C9 121.4(4) . . ? C7 C8 C9 118.1(4) . . ? O3 C9 O2 126.8(4) . . ? O3 C9 C8 121.7(4) . . ? O2 C9 C8 111.5(4) . . ? O4 C10 H10B 109.5 . . ? O4 C10 H10A 109.5 . . ? H10B C10 H10A 109.5 . . ? O4 C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? C1 N1 C7 109.1(3) . . ? C1 N1 H1 125(3) . . ? C7 N1 H1 126(3) . . ? C1 N2 C5 121.4(4) . . ? C1 N2 C6 109.1(3) . . ? C5 N2 C6 129.5(4) . . ? C10 O4 H2 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 179.6(5) . . . . ? N2 C1 C2 C3 -0.3(7) . . . . ? C1 C2 C3 C4 0.2(8) . . . . ? C2 C3 C4 C5 -0.4(9) . . . . ? C3 C4 C5 N2 0.6(8) . . . . ? N2 C6 C7 N1 -0.2(5) . . . . ? N2 C6 C7 C8 178.6(5) . . . . ? C6 C7 C8 O1 -176.0(5) . . . . ? N1 C7 C8 O1 2.7(7) . . . . ? C6 C7 C8 C9 0.5(7) . . . . ? N1 C7 C8 C9 179.1(4) . . . . ? O1 C8 C9 O3 -178.8(5) . . . . ? C7 C8 C9 O3 4.7(7) . . . . ? O1 C8 C9 O2 2.9(6) . . . . ? C7 C8 C9 O2 -173.5(4) . . . . ? N2 C1 N1 C7 0.7(5) . . . . ? C2 C1 N1 C7 -179.3(5) . . . . ? C6 C7 N1 C1 -0.3(5) . . . . ? C8 C7 N1 C1 -179.3(4) . . . . ? N1 C1 N2 C5 -179.4(4) . . . . ? C2 C1 N2 C5 0.6(7) . . . . ? N1 C1 N2 C6 -0.8(5) . . . . ? C2 C1 N2 C6 179.2(4) . . . . ? C4 C5 N2 C1 -0.7(7) . . . . ? C4 C5 N2 C6 -179.0(5) . . . . ? C7 C6 N2 C1 0.6(5) . . . . ? C7 C6 N2 C5 179.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.493 _refine_diff_density_min -0.926 _refine_diff_density_rms 0.072 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 859367' #TrackingRef '- Compd1-3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Cl N4 O7' _chemical_formula_weight 434.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 6.8215(14) _cell_length_b 11.724(2) _cell_length_c 11.570(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.04(3) _cell_angle_gamma 90.00 _cell_volume 901.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 446 _exptl_absorpt_coefficient_mu 0.266 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 0.943 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3840 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0654 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 24.40 _reflns_number_total 1482 _reflns_number_gt 890 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^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 SHELXL _refine_ls_extinction_coef 0.02(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1482 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2046 _refine_ls_R_factor_gt 0.1628 _refine_ls_wR_factor_ref 0.4937 _refine_ls_wR_factor_gt 0.4625 _refine_ls_goodness_of_fit_ref 1.698 _refine_ls_restrained_S_all 1.698 _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 Cl1 Cl 0.0000 -0.2986(9) 0.2500 0.253(5) Uani 1 2 d S . . C1 C 0.2482(11) 0.2507(8) 0.1842(8) 0.055(2) Uani 1 1 d . . . C2 C 0.2413(13) 0.3483(9) 0.2494(9) 0.068(3) Uani 1 1 d . . . H2A H 0.2323 0.3447 0.3284 0.082 Uiso 1 1 calc R . . C3 C 0.2480(14) 0.4492(9) 0.1946(10) 0.079(3) Uani 1 1 d . . . H3A H 0.2422 0.5161 0.2368 0.095 Uiso 1 1 calc R . . C4 C 0.2636(15) 0.4570(9) 0.0743(10) 0.083(3) Uani 1 1 d . . . H4A H 0.2676 0.5277 0.0385 0.099 Uiso 1 1 calc R . . C5 C 0.2725(15) 0.3610(10) 0.0135(9) 0.080(3) Uani 1 1 d . . . H5A H 0.2851 0.3645 -0.0648 0.097 Uiso 1 1 calc R . . C6 C 0.2676(12) 0.1469(8) 0.0263(7) 0.057(2) Uani 1 1 d . . . H6A H 0.2774 0.1262 -0.0498 0.068 Uiso 1 1 calc R . . C7 C 0.2560(10) 0.0770(8) 0.1131(7) 0.051(2) Uani 1 1 d . . . C8 C 0.2525(12) -0.0490(8) 0.1262(7) 0.058(2) Uani 1 1 d . . . C9 C 0.2453(13) -0.1231(8) 0.0131(8) 0.059(2) Uani 1 1 d . . . N1 N 0.2461(10) 0.1414(6) 0.2137(6) 0.056(2) Uani 1 1 d . . . H1A H 0.2399 0.1149 0.2821 0.067 Uiso 1 1 calc R . . N2 N 0.2627(10) 0.2547(6) 0.0679(6) 0.057(2) Uani 1 1 d . . . O1 O 0.2480(12) -0.0930(6) 0.2196(6) 0.090(3) Uani 1 1 d . . . O2 O 0.2659(14) -0.2244(7) 0.0294(6) 0.101(3) Uani 1 1 d . . . O3 O 0.2224(10) -0.0696(6) -0.0793(5) 0.076(2) Uani 1 1 d . . . O4 O 0.5000 -0.3232(11) 0.2500 0.116(6) Uani 1 2 d S . . H1 H 0.576(14) -0.285(8) 0.269(9) 0.06(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.281(14) 0.202(11) 0.263(11) 0.000 0.031(10) 0.000 C1 0.050(4) 0.053(6) 0.061(5) -0.003(4) 0.012(4) 0.013(4) C2 0.070(6) 0.060(6) 0.072(6) -0.006(5) 0.011(5) -0.009(4) C3 0.080(7) 0.054(6) 0.100(8) -0.015(6) 0.014(6) -0.009(5) C4 0.106(8) 0.047(6) 0.092(8) 0.002(6) 0.015(6) -0.010(5) C5 0.091(7) 0.080(8) 0.071(6) 0.022(6) 0.018(5) -0.013(5) C6 0.073(5) 0.060(6) 0.037(4) 0.006(4) 0.012(4) -0.001(4) C7 0.056(4) 0.052(5) 0.047(4) 0.001(4) 0.017(3) -0.003(4) C8 0.079(6) 0.055(6) 0.042(5) -0.001(4) 0.019(4) 0.007(4) C9 0.066(5) 0.050(6) 0.061(6) -0.005(5) 0.015(4) 0.000(4) N1 0.070(5) 0.052(5) 0.048(4) 0.001(3) 0.017(3) 0.003(3) N2 0.071(4) 0.050(5) 0.050(4) 0.008(3) 0.014(3) 0.001(3) O1 0.161(7) 0.053(4) 0.061(4) 0.011(4) 0.038(4) 0.016(4) O2 0.170(8) 0.053(5) 0.077(5) -0.012(4) 0.022(5) 0.006(4) O3 0.112(5) 0.076(5) 0.043(4) -0.001(3) 0.023(3) 0.007(4) O4 0.120(12) 0.044(7) 0.161(14) 0.000 -0.019(10) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.326(11) . ? C1 N2 1.372(11) . ? C1 C2 1.377(13) . ? C2 C3 1.349(14) . ? C3 C4 1.423(15) . ? C4 C5 1.335(15) . ? C5 N2 1.404(12) . ? C6 C7 1.313(11) . ? C6 N2 1.356(11) . ? C7 N1 1.402(11) . ? C7 C8 1.485(13) . ? C8 O1 1.204(9) . ? C8 C9 1.562(12) . ? C9 O2 1.207(12) . ? C9 O3 1.219(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 107.0(7) . . ? N1 C1 C2 131.1(9) . . ? N2 C1 C2 121.9(9) . . ? C3 C2 C1 117.5(9) . . ? C2 C3 C4 122.3(9) . . ? C5 C4 C3 118.9(9) . . ? C4 C5 N2 120.0(9) . . ? C7 C6 N2 107.5(7) . . ? C6 C7 N1 108.7(8) . . ? C6 C7 C8 134.7(8) . . ? N1 C7 C8 116.6(7) . . ? O1 C8 C7 121.4(8) . . ? O1 C8 C9 120.7(9) . . ? C7 C8 C9 117.8(7) . . ? O2 C9 O3 129.2(9) . . ? O2 C9 C8 115.8(9) . . ? O3 C9 C8 115.0(9) . . ? C1 N1 C7 107.6(7) . . ? C6 N2 C1 109.2(7) . . ? C6 N2 C5 131.4(8) . . ? C1 N2 C5 119.4(8) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.755 _refine_diff_density_min -0.635 _refine_diff_density_rms 0.149