# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email guanyangf@163.com _publ_contact_author_name 'Yang-Fan Guan' loop_ _publ_author_name 'Haibo Mei' 'Jianlin Han' 'Guigen Li' 'Yi Pan' data_2110328e_0m _database_code_depnum_ccdc_archive 'CCDC 820793' #TrackingRef '2110328E_0m-OK.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 Cl2 N2 O4' _chemical_formula_sum 'C13 H15 Cl2 N2 O4' _chemical_formula_weight 334.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.7762(8) _cell_length_b 9.6032(13) _cell_length_c 28.672(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1590.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max 26.360 _exptl_crystal_description rectangle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692.0 _exptl_absorpt_coefficient_mu 0.424 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.881 _exptl_absorpt_correction_T_max 0.903 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8921 _diffrn_reflns_av_R_equivalents 0.1228 _diffrn_reflns_av_sigmaI/netI 0.0829 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.36 _reflns_number_total 3236 _reflns_number_gt 2986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SHELXTL Program' _computing_data_reduction Saint _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL Program' _computing_publication_material 'Bruker SHELXTL Program' _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^)+(0.0675P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(8) _refine_ls_number_reflns 3236 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1346 _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 -0.00183(13) -0.30147(6) 0.09760(3) 0.0521(2) Uani 1 1 d . . . Cl2 Cl 0.44999(12) -0.18325(8) 0.08764(3) 0.0616(2) Uani 1 1 d . . . C1 C 0.0474(5) 0.1927(3) 0.06249(9) 0.0457(6) Uani 1 1 d . . . H1 H -0.0946 0.1605 0.0517 0.055 Uiso 1 1 calc R . . C7 C 0.0745(4) -0.0229(2) 0.11133(8) 0.0333(5) Uani 1 1 d . . . H7 H -0.0938 -0.0163 0.1076 0.040 Uiso 1 1 calc R . . C6 C 0.1753(4) 0.1135(2) 0.09381(8) 0.0342(5) Uani 1 1 d . . . C5 C 0.3886(5) 0.1624(2) 0.10922(9) 0.0417(6) Uani 1 1 d . . . H5 H 0.4766 0.1089 0.1296 0.050 Uiso 1 1 calc R . . C4 C 0.4713(5) 0.2912(3) 0.09424(11) 0.0533(7) Uani 1 1 d . . . H4 H 0.6125 0.3247 0.1051 0.064 Uiso 1 1 calc R . . C3 C 0.3416(6) 0.3687(3) 0.06318(11) 0.0607(9) Uani 1 1 d . . . H3 H 0.3969 0.4543 0.0529 0.073 Uiso 1 1 calc R . . C2 C 0.1334(7) 0.3213(3) 0.04733(11) 0.0610(8) Uani 1 1 d . . . H2 H 0.0483 0.3745 0.0264 0.073 Uiso 1 1 calc R . . O4 O 0.0251(3) -0.07399(18) 0.23423(6) 0.0417(4) Uani 1 1 d . . . N1 N 0.0944(5) -0.1186(2) 0.03063(8) 0.0464(6) Uani 1 1 d . . . O1 O -0.1098(5) -0.1123(3) 0.02199(8) 0.0644(7) Uani 1 1 d . . . O3 O -0.2628(4) -0.0340(2) 0.18137(7) 0.0524(5) Uani 1 1 d . . . O2 O 0.2502(5) -0.0945(3) 0.00396(9) 0.0774(8) Uani 1 1 d . . . C9 C -0.0617(5) -0.0511(2) 0.19124(8) 0.0368(6) Uani 1 1 d . . . N2 N 0.1178(4) -0.0495(2) 0.16043(7) 0.0401(5) Uani 1 1 d . . . C8 C 0.1547(4) -0.1510(2) 0.08269(9) 0.0373(5) Uani 1 1 d . . . C11 C -0.1295(5) -0.0889(3) 0.27498(8) 0.0411(6) Uani 1 1 d . . . C14 C 0.0403(6) -0.1209(4) 0.31356(10) 0.0624(8) Uani 1 1 d . . . H14A H 0.1165 -0.2076 0.3071 0.094 Uiso 1 1 calc R . . H14B H -0.0409 -0.1276 0.3427 0.094 Uiso 1 1 calc R . . H14C H 0.1533 -0.0478 0.3154 0.094 Uiso 1 1 calc R . . C12 C -0.2933(6) -0.2106(3) 0.26760(12) 0.0592(8) Uani 1 1 d . . . H12A H -0.3930 -0.1914 0.2416 0.089 Uiso 1 1 calc R . . H12B H -0.3852 -0.2241 0.2951 0.089 Uiso 1 1 calc R . . H12C H -0.2053 -0.2934 0.2614 0.089 Uiso 1 1 calc R . . C13 C -0.2589(7) 0.0467(3) 0.28380(13) 0.0662(9) Uani 1 1 d . . . H13A H -0.1503 0.1223 0.2852 0.099 Uiso 1 1 calc R . . H13B H -0.3410 0.0405 0.3128 0.099 Uiso 1 1 calc R . . H13C H -0.3668 0.0628 0.2589 0.099 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 Cl1 0.0624(4) 0.0401(3) 0.0539(4) 0.0088(2) -0.0062(4) -0.0046(3) Cl2 0.0418(3) 0.0594(4) 0.0836(6) -0.0218(4) -0.0022(4) 0.0092(3) C1 0.0597(15) 0.0467(12) 0.0308(12) 0.0021(10) 0.0004(13) 0.0127(15) C7 0.0392(12) 0.0399(10) 0.0207(10) 0.0004(9) -0.0003(10) 0.0062(10) C6 0.0462(13) 0.0337(10) 0.0227(10) -0.0028(8) 0.0044(10) 0.0080(10) C5 0.0494(14) 0.0403(12) 0.0355(13) -0.0003(10) 0.0045(12) 0.0049(11) C4 0.0603(16) 0.0480(13) 0.0516(17) -0.0072(11) 0.0106(16) -0.0066(14) C3 0.089(2) 0.0439(14) 0.0492(17) 0.0076(13) 0.0229(19) -0.0008(16) C2 0.094(2) 0.0463(14) 0.0427(16) 0.0114(12) 0.0014(19) 0.0155(18) O4 0.0507(10) 0.0520(9) 0.0224(8) 0.0073(6) 0.0010(9) -0.0007(9) N1 0.0719(17) 0.0379(11) 0.0294(11) -0.0048(9) 0.0094(12) -0.0013(12) O1 0.0780(15) 0.0706(14) 0.0447(12) 0.0111(11) -0.0209(13) -0.0096(13) O3 0.0515(11) 0.0739(13) 0.0317(10) 0.0100(9) 0.0026(9) 0.0117(11) O2 0.099(2) 0.0813(16) 0.0520(14) 0.0022(12) 0.0363(15) 0.0122(16) C9 0.0535(15) 0.0318(10) 0.0252(11) 0.0026(8) -0.0033(11) 0.0065(11) N2 0.0481(12) 0.0509(11) 0.0214(10) 0.0035(8) -0.0014(10) -0.0001(10) C8 0.0403(12) 0.0389(12) 0.0327(12) -0.0017(10) -0.0024(11) 0.0001(10) C11 0.0522(14) 0.0479(13) 0.0233(11) 0.0046(9) 0.0063(12) -0.0001(12) C14 0.0628(18) 0.095(2) 0.0293(14) 0.0126(14) 0.0006(15) 0.001(2) C12 0.0704(19) 0.0580(16) 0.0490(17) 0.0098(14) 0.0061(16) -0.0149(16) C13 0.091(2) 0.0617(17) 0.0458(16) -0.0047(15) 0.0123(19) 0.015(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 Cl1 C8 1.757(2) . ? Cl2 C8 1.740(3) . ? C1 C6 1.390(3) . ? C1 C2 1.400(4) . ? C1 H1 0.9300 . ? C7 N2 1.452(3) . ? C7 C6 1.518(3) . ? C7 C8 1.550(3) . ? C7 H7 0.9800 . ? C6 C5 1.391(4) . ? C5 C4 1.394(4) . ? C5 H5 0.9300 . ? C4 C3 1.381(5) . ? C4 H4 0.9300 . ? C3 C2 1.364(5) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? O4 C9 1.349(3) . ? O4 C11 1.478(3) . ? N1 O2 1.203(3) . ? N1 O1 1.207(4) . ? N1 C8 1.564(3) . ? O3 C9 1.207(3) . ? C9 N2 1.362(4) . ? C11 C12 1.519(4) . ? C11 C14 1.510(4) . ? C11 C13 1.522(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? 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 C6 C1 C2 119.7(3) . . ? C6 C1 H1 120.2 . . ? C2 C1 H1 120.2 . . ? N2 C7 C6 113.99(19) . . ? N2 C7 C8 108.80(18) . . ? C6 C7 C8 113.25(18) . . ? N2 C7 H7 106.8 . . ? C6 C7 H7 106.8 . . ? C8 C7 H7 106.8 . . ? C1 C6 C5 119.4(2) . . ? C1 C6 C7 118.8(2) . . ? C5 C6 C7 121.7(2) . . ? C4 C5 C6 120.4(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C2 C3 C4 120.9(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C9 O4 C11 120.9(2) . . ? O2 N1 O1 126.2(3) . . ? O2 N1 C8 118.6(2) . . ? O1 N1 C8 115.1(2) . . ? O3 C9 O4 126.5(3) . . ? O3 C9 N2 125.4(2) . . ? O4 C9 N2 108.2(2) . . ? C9 N2 C7 120.0(2) . . ? C7 C8 N1 106.33(18) . . ? C7 C8 Cl2 113.02(17) . . ? N1 C8 Cl2 109.36(18) . . ? C7 C8 Cl1 111.73(17) . . ? N1 C8 Cl1 106.33(16) . . ? Cl2 C8 Cl1 109.77(14) . . ? O4 C11 C12 109.9(2) . . ? O4 C11 C14 101.9(2) . . ? C12 C11 C14 110.5(2) . . ? O4 C11 C13 110.2(2) . . ? C12 C11 C13 112.1(3) . . ? C14 C11 C13 111.8(3) . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.444 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.081