# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_H2L(3) _database_code_depnum_ccdc_archive 'CCDC 897831' #TrackingRef 'H2L(3).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 Cl2 N2 O12' _chemical_formula_sum 'C18 H20 Cl2 N2 O12' _chemical_formula_weight 527.26 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 7.1914(4) _cell_length_b 7.9109(4) _cell_length_c 20.1775(11) _cell_angle_alpha 96.509(7) _cell_angle_beta 93.700(14) _cell_angle_gamma 93.897(10) _cell_volume 1134.84(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2226 _cell_measurement_theta_min 2.0372 _cell_measurement_theta_max 27.4934 _exptl_crystal_description plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.353 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9313 _exptl_absorpt_correction_T_max 1.0000 _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 Saturn70 _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1.0 _diffrn_reflns_number 7578 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0274 _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 -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4035 _reflns_number_gt 3044 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.0080P)^2^+1.8000P] 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 4035 _refine_ls_number_parameters 394 _refine_ls_number_restraints 738 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.264 _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 0.1750(4) 0.1669(4) 0.01060(16) 0.0696(9) Uani 1 1 d . . . O2 O 0.1235(5) 0.2652(4) -0.08725(15) 0.0708(9) Uani 1 1 d . . . H2 H 0.0793 0.1671 -0.0984 0.085 Uiso 1 1 calc R . . N1 N 0.3089(5) 0.7006(5) 0.21644(16) 0.0553(8) Uani 1 1 d . . . N2 N -0.4654(6) 0.7529(7) 0.40592(19) 0.0777(12) Uani 1 1 d . . . H2A H -0.5656 0.7577 0.4269 0.093 Uiso 1 1 calc R . . C1 C 0.1793(5) 0.2843(5) -0.0228(2) 0.0542(10) Uani 1 1 d . . . C2 C 0.2454(5) 0.4619(5) 0.0040(2) 0.0476(9) Uani 1 1 d . . . C3 C 0.2387(6) 0.5961(5) -0.0345(2) 0.0542(10) Uani 1 1 d . . . H3 H 0.1915 0.5766 -0.0789 0.065 Uiso 1 1 calc R . . C4 C 0.3024(6) 0.7591(5) -0.0066(2) 0.0603(11) Uani 1 1 d . . . H4 H 0.2969 0.8493 -0.0323 0.072 Uiso 1 1 calc R . . C5 C 0.3736(6) 0.7888(5) 0.0589(2) 0.0596(11) Uani 1 1 d . . . H5 H 0.4163 0.8989 0.0772 0.072 Uiso 1 1 calc R . . C6 C 0.3822(5) 0.6552(5) 0.0978(2) 0.0528(10) Uani 1 1 d . . . C7 C 0.3186(5) 0.4927(5) 0.0698(2) 0.0512(10) Uani 1 1 d . . . H7 H 0.3249 0.4025 0.0955 0.061 Uiso 1 1 calc R . . C8 C 0.4619(6) 0.6861(7) 0.1694(2) 0.0689(13) Uani 1 1 d . . . H8A H 0.5360 0.5928 0.1791 0.083 Uiso 1 1 calc R . . H8B H 0.5434 0.7904 0.1759 0.083 Uiso 1 1 calc R . . C9 C 0.2301(7) 0.8470(6) 0.2274(2) 0.0703(13) Uani 1 1 d . . . H9 H 0.2761 0.9413 0.2082 0.084 Uiso 1 1 calc R . . C10 C 0.0822(7) 0.8616(6) 0.2665(2) 0.0663(12) Uani 1 1 d . . . H10 H 0.0285 0.9653 0.2732 0.080 Uiso 1 1 calc R . . C11 C 0.0120(5) 0.7245(5) 0.29596(18) 0.0483(9) Uani 1 1 d . . . C12 C 0.0999(7) 0.5754(6) 0.2844(2) 0.0713(13) Uani 1 1 d . . . H12 H 0.0587 0.4798 0.3039 0.086 Uiso 1 1 calc R . . C13 C 0.2465(7) 0.5663(6) 0.2448(3) 0.0731(13) Uani 1 1 d . . . H13 H 0.3036 0.4645 0.2376 0.088 Uiso 1 1 calc R . . C14 C -0.1532(6) 0.7355(5) 0.33672(18) 0.0505(9) Uani 1 1 d . . . C15 C -0.2328(7) 0.8874(6) 0.3513(3) 0.0766(14) Uani 1 1 d . . . H15 H -0.1795 0.9868 0.3375 0.092 Uiso 1 1 calc R . . C16 C -0.3904(8) 0.8925(8) 0.3860(3) 0.0870(16) Uani 1 1 d . . . H16 H -0.4442 0.9953 0.3955 0.104 Uiso 1 1 calc R . . C17 C -0.3912(8) 0.6059(8) 0.3946(3) 0.0916(17) Uani 1 1 d . . . H17 H -0.4459 0.5095 0.4101 0.110 Uiso 1 1 calc R . . C18 C -0.2340(7) 0.5938(6) 0.3600(3) 0.0786(15) Uani 1 1 d . . . H18 H -0.1819 0.4895 0.3524 0.094 Uiso 1 1 calc R . . Cl1 Cl 0.64270(17) 0.21363(15) 0.21947(6) 0.0668(3) Uani 1 1 d D . . Cl2 Cl 0.18658(19) 0.24405(18) 0.42654(7) 0.0778(4) Uani 1 1 d D . . O3 O 0.7660(10) 0.3357(10) 0.2025(3) 0.159(4) Uani 0.754(8) 1 d PDU A 1 O4 O 0.6077(13) 0.2391(9) 0.2861(3) 0.156(4) Uani 0.754(8) 1 d PDU A 1 O5 O 0.4710(8) 0.2107(8) 0.1813(4) 0.143(3) Uani 0.754(8) 1 d PDU A 1 O6 O 0.7032(10) 0.0505(7) 0.2068(4) 0.146(3) Uani 0.754(8) 1 d PDU A 1 O3B O 0.525(3) 0.166(3) 0.2661(9) 0.183(11) Uani 0.246(8) 1 d PDU A 2 O4B O 0.634(3) 0.3857(11) 0.2140(11) 0.161(10) Uani 0.246(8) 1 d PDU A 2 O5B O 0.604(3) 0.118(2) 0.1592(6) 0.151(9) Uani 0.246(8) 1 d PDU A 2 O6B O 0.8267(15) 0.193(2) 0.2431(11) 0.148(9) Uani 0.246(8) 1 d PDU A 2 O7 O 0.3819(7) 0.2651(13) 0.4384(4) 0.131(4) Uani 0.661(12) 1 d PDU B 1 O8 O 0.1486(16) 0.2289(12) 0.3585(3) 0.146(4) Uani 0.661(12) 1 d PDU B 1 O9 O 0.1361(17) 0.0862(13) 0.4484(6) 0.205(6) Uani 0.661(12) 1 d PDU B 1 O10 O 0.1043(19) 0.3707(16) 0.4600(5) 0.227(6) Uani 0.661(12) 1 d PDU B 1 O7B O 0.327(3) 0.169(2) 0.3979(11) 0.234(11) Uani 0.339(12) 1 d PDU B 2 O8B O 0.034(2) 0.250(2) 0.3813(9) 0.161(9) Uani 0.339(12) 1 d PDU B 2 O9B O 0.124(2) 0.1653(15) 0.4798(6) 0.099(5) Uani 0.339(12) 1 d PDU B 2 O10B O 0.244(3) 0.4156(12) 0.4516(6) 0.133(7) Uani 0.339(12) 1 d PDU B 2 O1W O 0.0374(5) 0.0484(4) 0.12376(18) 0.0783(10) Uani 1 1 d D . . H1B H 0.077(7) 0.089(6) 0.0908(19) 0.118 Uiso 1 1 d D . . H1C H -0.039(7) 0.105(6) 0.143(2) 0.118 Uiso 1 1 d D . . O2W O 0.2164(9) 0.7639(12) 0.4657(4) 0.180(3) Uani 1 1 d D . . H2C H 0.154(15) 0.840(10) 0.481(6) 0.270 Uiso 1 1 d D . . H2D H 0.204(19) 0.673(8) 0.481(7) 0.270 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 0.077(2) 0.0534(18) 0.081(2) 0.0187(16) 0.0164(17) 0.0017(15) O2 0.077(2) 0.064(2) 0.069(2) 0.0043(16) 0.0084(17) -0.0065(17) N1 0.048(2) 0.064(2) 0.054(2) 0.0037(17) 0.0072(15) 0.0081(17) N2 0.056(3) 0.114(4) 0.063(2) 0.006(2) 0.0164(19) 0.001(2) C1 0.039(2) 0.057(3) 0.069(3) 0.009(2) 0.0172(19) 0.0066(18) C2 0.035(2) 0.051(2) 0.060(2) 0.0098(18) 0.0177(17) 0.0090(16) C3 0.048(2) 0.058(3) 0.060(2) 0.011(2) 0.0181(19) 0.0119(19) C4 0.062(3) 0.049(2) 0.076(3) 0.019(2) 0.022(2) 0.013(2) C5 0.051(3) 0.051(2) 0.078(3) 0.000(2) 0.024(2) 0.0045(19) C6 0.038(2) 0.060(3) 0.062(2) 0.003(2) 0.0172(18) 0.0088(18) C7 0.042(2) 0.054(2) 0.063(3) 0.0146(19) 0.0171(19) 0.0105(18) C8 0.047(3) 0.087(3) 0.073(3) 0.001(3) 0.014(2) 0.008(2) C9 0.075(3) 0.056(3) 0.085(3) 0.014(2) 0.032(3) 0.007(2) C10 0.077(3) 0.049(2) 0.078(3) 0.012(2) 0.030(3) 0.014(2) C11 0.052(2) 0.051(2) 0.041(2) 0.0050(17) 0.0008(17) 0.0032(18) C12 0.081(3) 0.056(3) 0.084(3) 0.023(2) 0.027(3) 0.016(2) C13 0.075(3) 0.061(3) 0.089(3) 0.016(3) 0.024(3) 0.024(2) C14 0.051(2) 0.057(2) 0.043(2) 0.0044(18) 0.0031(17) 0.0028(19) C15 0.074(3) 0.072(3) 0.092(4) 0.026(3) 0.034(3) 0.019(3) C16 0.079(4) 0.095(4) 0.096(4) 0.022(3) 0.032(3) 0.027(3) C17 0.088(4) 0.090(4) 0.098(4) 0.010(3) 0.035(3) -0.016(3) C18 0.084(4) 0.060(3) 0.093(4) 0.004(3) 0.032(3) -0.004(3) Cl1 0.0741(8) 0.0631(7) 0.0644(7) 0.0075(5) 0.0079(6) 0.0102(6) Cl2 0.0755(9) 0.0863(9) 0.0747(8) 0.0142(7) 0.0216(7) 0.0051(7) O3 0.149(7) 0.183(8) 0.136(6) 0.056(6) 0.000(5) -0.093(6) O4 0.230(10) 0.139(6) 0.090(5) -0.023(4) 0.057(5) -0.030(6) O5 0.107(5) 0.114(5) 0.208(8) 0.054(5) -0.061(5) 0.009(4) O6 0.137(6) 0.095(5) 0.202(8) -0.022(5) -0.001(5) 0.054(4) O3B 0.18(2) 0.22(2) 0.147(19) 0.014(17) 0.075(17) -0.051(18) O4B 0.20(2) 0.059(10) 0.23(2) 0.030(12) -0.015(18) 0.063(13) O5B 0.19(2) 0.156(18) 0.084(12) -0.049(12) -0.023(13) -0.023(16) O6B 0.108(14) 0.127(16) 0.207(19) 0.028(14) -0.059(13) 0.047(12) O7 0.081(5) 0.170(9) 0.140(7) 0.004(6) 0.034(4) -0.019(5) O8 0.221(12) 0.133(7) 0.081(5) 0.009(4) -0.001(6) 0.011(8) O9 0.274(13) 0.163(10) 0.182(10) 0.098(9) 0.010(10) -0.068(9) O10 0.236(13) 0.217(13) 0.237(11) -0.036(10) 0.107(10) 0.110(10) O7B 0.21(2) 0.22(2) 0.28(2) -0.033(18) 0.099(18) 0.101(16) O8B 0.154(15) 0.101(11) 0.220(18) 0.056(13) -0.099(13) -0.008(11) O9B 0.108(10) 0.105(10) 0.089(9) 0.016(7) 0.052(7) -0.005(8) O10B 0.171(15) 0.083(9) 0.131(11) -0.038(7) 0.067(10) -0.068(10) O1W 0.080(3) 0.084(2) 0.071(2) 0.0062(19) 0.0167(18) -0.0007(19) O2W 0.088(4) 0.301(9) 0.160(5) 0.023(6) 0.065(3) 0.034(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 O1 C1 1.207(5) . ? O2 C1 1.325(5) . ? O2 H2 0.8200 . ? N1 C9 1.326(5) . ? N1 C13 1.328(5) . ? N1 C8 1.501(5) . ? N2 C16 1.311(6) . ? N2 C17 1.315(7) . ? N2 H2A 0.8600 . ? C1 C2 1.482(6) . ? C2 C7 1.385(5) . ? C2 C3 1.386(5) . ? C3 C4 1.382(6) . ? C3 H3 0.9300 . ? C4 C5 1.374(6) . ? C4 H4 0.9300 . ? C5 C6 1.388(6) . ? C5 H5 0.9300 . ? C6 C7 1.379(5) . ? C6 C8 1.507(6) . ? C7 H7 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.367(6) . ? C9 H9 0.9300 . ? C10 C11 1.377(5) . ? C10 H10 0.9300 . ? C11 C12 1.380(6) . ? C11 C14 1.490(5) . ? C12 C13 1.364(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C18 1.371(6) . ? C14 C15 1.376(6) . ? C15 C16 1.371(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.369(7) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? Cl1 O3 1.353(4) . ? Cl1 O5B 1.359(7) . ? Cl1 O3B 1.370(8) . ? Cl1 O4 1.379(5) . ? Cl1 O4B 1.384(7) . ? Cl1 O6 1.391(4) . ? Cl1 O6B 1.404(7) . ? Cl1 O5 1.410(4) . ? Cl2 O7B 1.334(7) . ? Cl2 O10 1.338(6) . ? Cl2 O8 1.372(5) . ? Cl2 O9B 1.385(7) . ? Cl2 O8B 1.388(7) . ? Cl2 O9 1.403(6) . ? Cl2 O7 1.405(5) . ? Cl2 O10B 1.417(7) . ? O1W H1B 0.828(13) . ? O1W H1C 0.823(13) . ? O2W H2C 0.817(13) . ? O2W H2D 0.818(13) . ? 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 O2 H2 109.5 . . ? C9 N1 C13 119.8(4) . . ? C9 N1 C8 119.5(4) . . ? C13 N1 C8 120.6(4) . . ? C16 N2 C17 121.6(5) . . ? C16 N2 H2A 119.2 . . ? C17 N2 H2A 119.2 . . ? O1 C1 O2 122.5(4) . . ? O1 C1 C2 123.7(4) . . ? O2 C1 C2 113.8(4) . . ? C7 C2 C3 119.4(4) . . ? C7 C2 C1 118.1(4) . . ? C3 C2 C1 122.5(4) . . ? C4 C3 C2 119.8(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.4(4) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.3(4) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 119.2(4) . . ? C7 C6 C8 120.2(4) . . ? C5 C6 C8 120.7(4) . . ? C6 C7 C2 120.9(4) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? N1 C8 C6 110.9(3) . . ? N1 C8 H8A 109.5 . . ? C6 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? N1 C9 C10 121.1(4) . . ? N1 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C9 C10 C11 120.7(4) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C12 116.5(4) . . ? C10 C11 C14 121.7(4) . . ? C12 C11 C14 121.8(4) . . ? C13 C12 C11 120.8(4) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? N1 C13 C12 121.1(4) . . ? N1 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C18 C14 C15 117.5(4) . . ? C18 C14 C11 121.2(4) . . ? C15 C14 C11 121.3(4) . . ? C16 C15 C14 120.1(5) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? N2 C16 C15 120.2(5) . . ? N2 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N2 C17 C18 120.5(5) . . ? N2 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C17 C18 C14 120.0(5) . . ? C17 C18 H18 120.0 . . ? C14 C18 H18 120.0 . . ? O3 Cl1 O5B 100.4(9) . . ? O3 Cl1 O3B 146.3(10) . . ? O5B Cl1 O3B 111.9(7) . . ? O3 Cl1 O4 112.2(4) . . ? O5B Cl1 O4 147.4(8) . . ? O3B Cl1 O4 35.8(9) . . ? O3 Cl1 O4B 46.6(8) . . ? O5B Cl1 O4B 111.2(7) . . ? O3B Cl1 O4B 109.6(7) . . ? O4 Cl1 O4B 91.1(10) . . ? O3 Cl1 O6 112.5(4) . . ? O5B Cl1 O6 58.5(9) . . ? O3B Cl1 O6 93.0(11) . . ? O4 Cl1 O6 107.6(4) . . ? O4B Cl1 O6 157.4(10) . . ? O3 Cl1 O6B 67.8(8) . . ? O5B Cl1 O6B 109.4(7) . . ? O3B Cl1 O6B 108.1(7) . . ? O4 Cl1 O6B 85.2(10) . . ? O4B Cl1 O6B 106.4(7) . . ? O6 Cl1 O6B 63.9(7) . . ? O3 Cl1 O5 110.6(4) . . ? O5B Cl1 O5 56.5(9) . . ? O3B Cl1 O5 81.2(10) . . ? O4 Cl1 O5 107.9(4) . . ? O4B Cl1 O5 79.6(8) . . ? O6 Cl1 O5 105.7(4) . . ? O6B Cl1 O5 165.8(8) . . ? O7B Cl2 O10 155.9(9) . . ? O7B Cl2 O8 72.1(9) . . ? O10 Cl2 O8 114.0(5) . . ? O7B Cl2 O9B 113.4(7) . . ? O10 Cl2 O9B 78.8(7) . . ? O8 Cl2 O9B 137.2(7) . . ? O7B Cl2 O8B 112.1(7) . . ? O10 Cl2 O8B 81.5(10) . . ? O8 Cl2 O8B 41.8(9) . . ? O9B Cl2 O8B 107.7(7) . . ? O7B Cl2 O9 87.0(9) . . ? O10 Cl2 O9 111.4(5) . . ? O8 Cl2 O9 108.0(5) . . ? O9B Cl2 O9 35.6(6) . . ? O8B Cl2 O9 98.3(9) . . ? O7B Cl2 O7 46.6(9) . . ? O10 Cl2 O7 111.3(5) . . ? O8 Cl2 O7 106.9(5) . . ? O9B Cl2 O7 105.1(7) . . ? O8B Cl2 O7 146.6(9) . . ? O9 Cl2 O7 104.7(5) . . ? O7B Cl2 O10B 110.2(7) . . ? O10 Cl2 O10B 45.7(6) . . ? O8 Cl2 O10B 110.4(8) . . ? O9B Cl2 O10B 106.9(6) . . ? O8B Cl2 O10B 106.2(6) . . ? O9 Cl2 O10B 141.2(7) . . ? O7 Cl2 O10B 69.6(7) . . ? H1B O1W H1C 114(2) . . ? H2C O2W H2D 116(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O1W 0.82 1.85 2.669(5) 175.8 2 N2 H2A O2W 0.86 1.80 2.656(6) 176.3 1_455 O1W H1B O1 0.828(13) 1.952(13) 2.779(5) 175(5) . O1W H1C O6 0.823(13) 2.37(4) 3.018(8) 136(5) 1_455 O1W H1C O6B 0.823(13) 2.35(4) 3.08(2) 148(5) 1_455 O1W H1C O3 0.823(13) 2.61(2) 3.419(10) 169(5) 1_455 O2W H2C O9B 0.817(13) 2.20(9) 2.814(14) 132(11) 2_566 O2W H2C O9 0.817(13) 2.66(7) 3.369(16) 146(11) 2_566 O2W H2D O10 0.818(13) 2.60(11) 3.029(16) 114(10) 2_566 O2W H2D O10B 0.818(13) 2.10(8) 2.760(15) 137(12) . O2W H2D O10 0.818(13) 2.43(8) 3.147(17) 146(14) . _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.405 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.048 data_HL _database_code_depnum_ccdc_archive 'CCDC 897832' #TrackingRef '897832.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 Cl N2 O7' _chemical_formula_sum 'C18 H17 Cl N2 O7' _chemical_formula_weight 408.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.2324(2) _cell_length_b 21.4758(6) _cell_length_c 9.4940(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.749(2) _cell_angle_gamma 90.00 _cell_volume 1869.36(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3222 _cell_measurement_theta_min 4.1136 _cell_measurement_theta_max 65.2271 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 2.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.52284 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 10.3503 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1.0 _diffrn_reflns_number 6354 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 65.33 _reflns_number_total 3117 _reflns_number_gt 2550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.36.20' _computing_cell_refinement 'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.36.20' _computing_data_reduction 'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.36.20' _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^)+(0.0500P)^2^+2.0000P] 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 0.0036(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3117 _refine_ls_number_parameters 310 _refine_ls_number_restraints 268 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0702 _refine_ls_wR_factor_ref 0.1705 _refine_ls_wR_factor_gt 0.1629 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.142 _refine_ls_shift/su_max 0.033 _refine_ls_shift/su_mean 0.003 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 0.4674(3) 0.39117(14) 0.2982(3) 0.0898(9) Uani 1 1 d . . . O2 O 0.4838(3) 0.37045(13) 0.5279(3) 0.0853(9) Uani 1 1 d . . . H2 H 0.5429 0.3991 0.5322 0.102 Uiso 1 1 calc R . . N1 N 0.2422(3) 0.15528(13) 0.6686(3) 0.0608(8) Uani 1 1 d . . . N2 N 0.8146(4) -0.04247(17) 0.9319(5) 0.0932(12) Uani 1 1 d . . . C1 C 0.4308(4) 0.36128(17) 0.3957(5) 0.0658(9) Uani 1 1 d . . . C2 C 0.3217(3) 0.31008(15) 0.3787(4) 0.0558(8) Uani 1 1 d . . . C3 C 0.2626(4) 0.29357(18) 0.2432(4) 0.0654(9) Uani 1 1 d . . . H3 H 0.2902 0.3149 0.1653 0.078 Uiso 1 1 calc R . . C4 C 0.1632(4) 0.24581(19) 0.2231(4) 0.0714(10) Uani 1 1 d . . . H4 H 0.1249 0.2345 0.1317 0.086 Uiso 1 1 calc R . . C5 C 0.1200(4) 0.21456(17) 0.3388(4) 0.0657(10) Uani 1 1 d . . . H5 H 0.0528 0.1822 0.3248 0.079 Uiso 1 1 calc R . . C6 C 0.1762(3) 0.23124(15) 0.4751(4) 0.0568(8) Uani 1 1 d . . . C7 C 0.2772(3) 0.27919(15) 0.4948(4) 0.0560(8) Uani 1 1 d . . . H7 H 0.3152 0.2907 0.5861 0.067 Uiso 1 1 calc R . . C8 C 0.1261(4) 0.19810(18) 0.6011(4) 0.0683(10) Uani 1 1 d . . . H8A H 0.1022 0.2286 0.6702 0.082 Uiso 1 1 calc R . . H8B H 0.0387 0.1743 0.5706 0.082 Uiso 1 1 calc R . . C9 C 0.2583(5) 0.09964(19) 0.6102(4) 0.0779(11) Uani 1 1 d . . . H9 H 0.1945 0.0873 0.5321 0.093 Uiso 1 1 calc R . . C10 C 0.3679(5) 0.06064(19) 0.6641(4) 0.0773(11) Uani 1 1 d . . . H10 H 0.3776 0.0218 0.6228 0.093 Uiso 1 1 calc R . . C11 C 0.4655(3) 0.07841(15) 0.7807(4) 0.0581(8) Uani 1 1 d . . . C12 C 0.4397(4) 0.13462(17) 0.8409(5) 0.0716(10) Uani 1 1 d . . . H12 H 0.4991 0.1476 0.9215 0.086 Uiso 1 1 calc R . . C13 C 0.3277(4) 0.17209(18) 0.7840(5) 0.0734(11) Uani 1 1 d . . . H13 H 0.3115 0.2099 0.8272 0.088 Uiso 1 1 calc R . . C14 C 0.5880(4) 0.03741(16) 0.8356(4) 0.0624(9) Uani 1 1 d . . . C15 C 0.6327(6) -0.0093(3) 0.7531(6) 0.122(2) Uani 1 1 d . . . H15 H 0.5867 -0.0149 0.6614 0.147 Uiso 1 1 calc R . . C16 C 0.7447(7) -0.0479(3) 0.8045(7) 0.144(3) Uani 1 1 d . . . H16 H 0.7722 -0.0795 0.7461 0.173 Uiso 1 1 calc R . . C17 C 0.7737(4) 0.0015(2) 1.0136(5) 0.0781(12) Uani 1 1 d . . . H17 H 0.8220 0.0058 1.1047 0.094 Uiso 1 1 calc R . . C18 C 0.6596(4) 0.04265(18) 0.9688(4) 0.0687(10) Uani 1 1 d . . . H18 H 0.6330 0.0734 1.0298 0.082 Uiso 1 1 calc R . . Cl1 Cl 0.6105(6) 0.1486(3) 0.3537(7) 0.0794(18) Uani 0.479(12) 1 d PDU A 1 O3 O 0.6528(12) 0.0876(3) 0.3983(19) 0.154(5) Uani 0.479(12) 1 d PDU A 1 O4 O 0.7344(12) 0.1865(6) 0.3750(19) 0.158(6) Uani 0.479(12) 1 d PDU A 1 O5 O 0.5591(18) 0.1465(9) 0.2086(8) 0.154(5) Uani 0.479(12) 1 d PDU A 1 O6 O 0.5042(11) 0.1686(7) 0.4331(12) 0.175(5) Uani 0.479(12) 1 d PDU A 1 Cl1B Cl 0.6303(9) 0.1439(3) 0.3413(8) 0.121(3) Uani 0.521(12) 1 d PDU A 2 O3B O 0.7174(14) 0.0960(5) 0.2988(14) 0.179(5) Uani 0.521(12) 1 d PDU A 2 O4B O 0.5536(16) 0.1234(7) 0.4498(9) 0.167(5) Uani 0.521(12) 1 d PDU A 2 O5B O 0.5306(14) 0.1611(6) 0.2220(12) 0.133(4) Uani 0.521(12) 1 d PDU A 2 O6B O 0.7141(14) 0.1956(5) 0.3870(14) 0.149(5) Uani 0.521(12) 1 d PDU A 2 O1W O 0.4298(15) 0.4461(6) 0.0199(17) 0.232(8) Uani 0.50 1 d P . . O2W O 0.4808(13) 0.4447(8) -0.1234(14) 0.222(7) Uani 0.50 1 d P . . 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 0.093(2) 0.0761(19) 0.107(2) -0.0017(17) 0.0374(17) -0.0253(16) O2 0.0734(18) 0.0691(18) 0.106(2) 0.0088(16) -0.0205(15) -0.0199(14) N1 0.0518(15) 0.0547(17) 0.0766(19) 0.0137(14) 0.0103(14) 0.0046(13) N2 0.083(2) 0.068(2) 0.123(3) 0.001(2) -0.014(2) 0.0201(19) C1 0.0504(19) 0.056(2) 0.090(3) -0.005(2) 0.0061(19) 0.0029(16) C2 0.0409(16) 0.0529(18) 0.074(2) 0.0002(16) 0.0059(15) 0.0025(14) C3 0.0577(19) 0.070(2) 0.069(2) 0.0019(18) 0.0107(16) -0.0010(17) C4 0.066(2) 0.076(2) 0.071(2) -0.008(2) -0.0005(18) -0.0070(19) C5 0.0502(18) 0.057(2) 0.088(3) -0.0005(19) -0.0010(17) -0.0042(16) C6 0.0415(16) 0.0534(19) 0.075(2) 0.0095(16) 0.0049(15) 0.0048(14) C7 0.0439(16) 0.0561(19) 0.067(2) 0.0018(16) 0.0000(14) 0.0041(14) C8 0.0488(18) 0.065(2) 0.092(3) 0.019(2) 0.0110(17) 0.0080(16) C9 0.082(3) 0.071(3) 0.077(3) 0.002(2) -0.006(2) 0.010(2) C10 0.086(3) 0.062(2) 0.080(3) -0.005(2) -0.006(2) 0.017(2) C11 0.0515(18) 0.0477(18) 0.076(2) 0.0095(16) 0.0122(16) -0.0011(14) C12 0.064(2) 0.055(2) 0.092(3) -0.0062(19) -0.0090(19) 0.0029(17) C13 0.064(2) 0.054(2) 0.100(3) -0.008(2) 0.001(2) 0.0080(17) C14 0.0533(18) 0.0516(19) 0.081(2) 0.0059(17) 0.0013(17) 0.0011(15) C15 0.111(4) 0.114(4) 0.129(4) -0.044(3) -0.037(3) 0.060(3) C16 0.134(5) 0.124(5) 0.157(6) -0.053(4) -0.057(4) 0.077(4) C17 0.062(2) 0.084(3) 0.086(3) 0.021(2) 0.000(2) -0.008(2) C18 0.059(2) 0.063(2) 0.084(3) 0.0107(19) 0.0112(18) 0.0017(17) Cl1 0.082(2) 0.066(3) 0.090(4) -0.004(2) 0.0097(19) 0.0057(19) O3 0.152(8) 0.067(5) 0.237(12) 0.029(6) -0.004(8) 0.004(5) O4 0.159(9) 0.160(11) 0.151(11) 0.029(9) 0.004(8) -0.099(9) O5 0.214(11) 0.176(12) 0.078(7) -0.038(7) 0.034(7) -0.060(9) O6 0.173(8) 0.192(11) 0.167(9) -0.022(8) 0.047(7) 0.064(8) Cl1B 0.191(6) 0.097(4) 0.080(3) -0.007(3) 0.035(3) -0.060(4) O3B 0.235(11) 0.159(9) 0.143(9) -0.017(7) 0.020(8) 0.029(8) O4B 0.237(10) 0.173(10) 0.103(5) -0.002(6) 0.075(6) -0.112(8) O5B 0.153(8) 0.120(7) 0.116(8) 0.005(6) -0.023(7) -0.004(6) O6B 0.257(12) 0.106(7) 0.083(6) -0.003(6) 0.014(7) -0.083(8) O1W 0.229(13) 0.183(11) 0.252(14) 0.110(11) -0.110(12) -0.092(10) O2W 0.177(10) 0.326(19) 0.154(9) -0.015(10) -0.018(8) 0.139(12) _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 O1 C1 1.207(5) . ? O2 C1 1.307(5) . ? O2 H2 0.8200 . ? N1 C13 1.323(5) . ? N1 C9 1.333(5) . ? N1 C8 1.498(4) . ? N2 C17 1.307(6) . ? N2 C16 1.308(6) . ? C1 C2 1.487(5) . ? C2 C7 1.389(5) . ? C2 C3 1.383(5) . ? C3 C4 1.375(5) . ? C3 H3 0.9300 . ? C4 C5 1.385(5) . ? C4 H4 0.9300 . ? C5 C6 1.383(5) . ? C5 H5 0.9300 . ? C6 C7 1.387(4) . ? C6 C8 1.511(5) . ? C7 H7 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.366(5) . ? C9 H9 0.9300 . ? C10 C11 1.395(5) . ? C10 H10 0.9300 . ? C11 C12 1.368(5) . ? C11 C14 1.479(5) . ? C12 C13 1.370(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C18 1.361(5) . ? C14 C15 1.365(6) . ? C15 C16 1.371(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.402(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? Cl1 O6 1.375(6) . ? Cl1 O4 1.399(6) . ? Cl1 O5 1.404(6) . ? Cl1 O3 1.417(6) . ? Cl1B O3B 1.394(7) . ? Cl1B O4B 1.388(6) . ? Cl1B O6B 1.393(6) . ? Cl1B O5B 1.422(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 H2 109.5 . . ? C13 N1 C9 120.3(3) . . ? C13 N1 C8 120.9(3) . . ? C9 N1 C8 118.8(3) . . ? C17 N2 C16 117.9(4) . . ? O1 C1 O2 123.3(4) . . ? O1 C1 C2 123.9(4) . . ? O2 C1 C2 112.8(3) . . ? C7 C2 C3 119.6(3) . . ? C7 C2 C1 121.8(3) . . ? C3 C2 C1 118.6(3) . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.1(4) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.3(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 119.4(3) . . ? C5 C6 C8 120.2(3) . . ? C7 C6 C8 120.4(3) . . ? C2 C7 C6 120.3(3) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? N1 C8 C6 111.0(3) . . ? N1 C8 H8A 109.4 . . ? C6 C8 H8A 109.4 . . ? N1 C8 H8B 109.4 . . ? C6 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N1 C9 C10 120.5(4) . . ? N1 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C9 C10 C11 120.7(4) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 116.4(3) . . ? C12 C11 C14 122.8(3) . . ? C10 C11 C14 120.8(3) . . ? C11 C12 C13 120.9(4) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? N1 C13 C12 121.0(4) . . ? N1 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C18 C14 C15 116.6(4) . . ? C18 C14 C11 123.1(3) . . ? C15 C14 C11 120.3(4) . . ? C14 C15 C16 120.4(5) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? N2 C16 C15 123.0(5) . . ? N2 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? N2 C17 C18 122.3(4) . . ? N2 C17 H17 118.8 . . ? C18 C17 H17 118.8 . . ? C14 C18 C17 119.7(4) . . ? C14 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? O6 Cl1 O4 111.3(6) . . ? O6 Cl1 O5 111.6(6) . . ? O4 Cl1 O5 109.7(6) . . ? O6 Cl1 O3 108.3(6) . . ? O4 Cl1 O3 107.6(5) . . ? O5 Cl1 O3 108.2(6) . . ? O3B Cl1B O4B 110.0(6) . . ? O3B Cl1B O6B 111.1(6) . . ? O4B Cl1B O6B 109.6(5) . . ? O3B Cl1B O5B 107.6(5) . . ? O4B Cl1B O5B 109.5(6) . . ? O6B Cl1B O5B 108.9(5) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 65.33 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.373 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.050 data_L(1) _database_code_depnum_ccdc_archive 'CCDC 897833' #TrackingRef 'L(1).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 N2 O7' _chemical_formula_sum 'C18 H24 N2 O7' _chemical_formula_weight 380.39 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 27.357(5) _cell_length_b 8.6859(8) _cell_length_c 18.312(3) _cell_angle_alpha 90.00 _cell_angle_beta 119.076(7) _cell_angle_gamma 90.00 _cell_volume 3803.0(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5847 _cell_measurement_theta_min 2.2728 _cell_measurement_theta_max 27.4739 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6474 _exptl_absorpt_correction_T_max 1.0000 _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 Saturn70 _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1.0 _diffrn_reflns_number 15615 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4317 _reflns_number_gt 2571 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _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^)+(0.1585P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4317 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1174 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_ref 0.2800 _refine_ls_wR_factor_gt 0.2041 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 N1 N 0.13303(9) 0.4864(3) 0.05149(14) 0.0428(6) Uani 1 1 d . . . N2 N -0.10666(11) 0.9536(3) -0.07893(18) 0.0578(7) Uani 1 1 d . . . O1 O 0.31105(8) 0.8679(3) 0.21298(13) 0.0532(6) Uani 1 1 d . . . O1W O 0.45505(10) 1.0556(3) 0.26441(15) 0.0645(7) Uani 1 1 d . . . O2 O 0.38123(9) 0.8248(3) 0.18589(15) 0.0604(6) Uani 1 1 d . . . O2W O 0.30527(12) 1.1965(3) 0.18954(15) 0.0751(8) Uani 1 1 d . . . O3W O 0.20116(12) 0.8577(4) 0.18634(19) 0.0910(10) Uani 1 1 d . . . O4W O 0.05526(10) 0.0739(3) 0.31210(16) 0.0733(8) Uani 1 1 d . . . O5W O 0.10859(13) 0.7873(4) 0.3442(2) 0.1002(10) Uani 1 1 d . . . C1 C 0.33385(11) 0.7969(3) 0.17748(17) 0.0422(6) Uani 1 1 d . . . C2 C 0.30102(10) 0.6691(3) 0.11745(16) 0.0381(6) Uani 1 1 d . . . C3 C 0.31072(11) 0.6310(3) 0.05151(16) 0.0417(6) Uani 1 1 d . . . H3 H 0.3396 0.6821 0.0463 0.050 Uiso 1 1 calc R . . C4 C 0.27936(12) 0.5214(4) -0.00568(18) 0.0464(7) Uani 1 1 d . . . H4 H 0.2859 0.4986 -0.0510 0.056 Uiso 1 1 calc R . . C5 C 0.23809(12) 0.4435(3) 0.00237(18) 0.0453(7) Uani 1 1 d . . . H5 H 0.2163 0.3676 -0.0377 0.054 Uiso 1 1 calc R . . C6 C 0.22840(11) 0.4752(3) 0.06827(17) 0.0404(6) Uani 1 1 d . . . C7 C 0.25967(11) 0.5873(3) 0.12552(17) 0.0393(6) Uani 1 1 d . . . H7 H 0.2531 0.6093 0.1708 0.047 Uiso 1 1 calc R . . C8 C 0.18424(12) 0.3883(4) 0.0772(2) 0.0528(8) Uani 1 1 d . . . H8A H 0.1992 0.3555 0.1360 0.063 Uiso 1 1 calc R . . H8B H 0.1739 0.2947 0.0419 0.063 Uiso 1 1 calc R . . C9 C 0.11636(13) 0.5251(4) 0.10574(19) 0.0514(8) Uani 1 1 d . . . H9 H 0.1369 0.4901 0.1618 0.062 Uiso 1 1 calc R . . C10 C 0.07005(13) 0.6147(4) 0.08226(18) 0.0549(8) Uani 1 1 d . . . H10 H 0.0585 0.6393 0.1221 0.066 Uiso 1 1 calc R . . C11 C 0.03955(11) 0.6706(3) 0.00106(15) 0.0393(6) Uani 1 1 d . . . C12 C 0.05801(13) 0.6248(5) -0.05406(18) 0.0560(9) Uani 1 1 d . . . H12 H 0.0380 0.6566 -0.1108 0.067 Uiso 1 1 calc R . . C13 C 0.10417(13) 0.5355(4) -0.02825(19) 0.0577(9) Uani 1 1 d . . . H13 H 0.1163 0.5071 -0.0669 0.069 Uiso 1 1 calc R . . C14 C -0.01093(10) 0.7683(3) -0.02628(16) 0.0395(6) Uani 1 1 d . . . C15 C -0.02970(14) 0.8158(4) 0.0283(2) 0.0552(8) Uani 1 1 d . . . H15 H -0.0103 0.7850 0.0852 0.066 Uiso 1 1 calc R . . C16 C -0.07658(15) 0.9079(5) -0.0003(2) 0.0634(9) Uani 1 1 d . . . H16 H -0.0880 0.9403 0.0387 0.076 Uiso 1 1 calc R . . C17 C -0.08929(15) 0.9053(5) -0.1317(2) 0.0650(10) Uani 1 1 d . . . H17 H -0.1104 0.9341 -0.1888 0.078 Uiso 1 1 calc R . . C18 C -0.04236(14) 0.8158(5) -0.10744(19) 0.0620(10) Uani 1 1 d . . . H18 H -0.0316 0.7866 -0.1476 0.074 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 N1 0.0381(12) 0.0408(13) 0.0434(13) 0.0041(10) 0.0150(10) -0.0047(10) N2 0.0477(15) 0.0561(18) 0.0681(18) -0.0032(14) 0.0270(14) 0.0002(12) O1 0.0512(12) 0.0496(13) 0.0549(12) -0.0166(10) 0.0227(10) -0.0049(10) O1W 0.0600(14) 0.0674(17) 0.0720(15) -0.0088(12) 0.0368(12) -0.0099(12) O2 0.0434(12) 0.0566(15) 0.0752(15) -0.0135(12) 0.0241(11) -0.0128(10) O2W 0.104(2) 0.0602(17) 0.0670(16) 0.0039(12) 0.0466(15) 0.0126(14) O3W 0.0889(19) 0.098(2) 0.117(2) 0.0505(19) 0.0740(19) 0.0342(17) O4W 0.0542(14) 0.085(2) 0.0736(16) -0.0026(14) 0.0255(13) -0.0095(13) O5W 0.091(2) 0.083(2) 0.125(3) -0.019(2) 0.052(2) -0.0075(18) C1 0.0418(14) 0.0362(15) 0.0419(14) 0.0014(12) 0.0150(12) 0.0004(11) C2 0.0338(12) 0.0358(14) 0.0376(13) 0.0011(11) 0.0119(11) 0.0058(10) C3 0.0395(13) 0.0441(16) 0.0410(14) 0.0027(12) 0.0191(12) 0.0047(12) C4 0.0487(16) 0.0462(17) 0.0397(14) -0.0012(12) 0.0179(12) 0.0082(13) C5 0.0431(15) 0.0354(15) 0.0436(15) -0.0048(12) 0.0103(12) 0.0030(12) C6 0.0346(13) 0.0325(14) 0.0457(15) 0.0032(11) 0.0131(11) 0.0041(11) C7 0.0387(13) 0.0333(14) 0.0429(14) -0.0005(11) 0.0175(12) 0.0026(11) C8 0.0433(16) 0.0380(16) 0.068(2) 0.0087(14) 0.0200(15) -0.0015(12) C9 0.0502(17) 0.059(2) 0.0374(14) 0.0065(14) 0.0151(13) 0.0019(14) C10 0.0576(18) 0.070(2) 0.0356(15) 0.0022(14) 0.0217(14) 0.0070(16) C11 0.0401(14) 0.0425(15) 0.0334(13) -0.0006(11) 0.0165(11) -0.0093(11) C12 0.0498(17) 0.080(2) 0.0343(15) 0.0068(15) 0.0177(13) 0.0124(16) C13 0.0530(18) 0.074(2) 0.0455(17) 0.0054(16) 0.0237(15) 0.0107(16) C14 0.0369(13) 0.0380(15) 0.0433(14) -0.0014(12) 0.0193(12) -0.0070(11) C15 0.0535(17) 0.065(2) 0.0518(17) 0.0013(15) 0.0290(14) 0.0030(16) C16 0.062(2) 0.071(3) 0.069(2) -0.0011(18) 0.0410(19) 0.0050(17) C17 0.058(2) 0.078(3) 0.0497(18) 0.0040(17) 0.0188(16) 0.0169(18) C18 0.0579(19) 0.082(3) 0.0432(17) 0.0022(16) 0.0226(15) 0.0199(18) _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 C9 1.322(4) . ? N1 C13 1.348(4) . ? N1 C8 1.507(4) . ? N2 C16 1.326(5) . ? N2 C17 1.335(4) . ? O1 C1 1.260(3) . ? O2 C1 1.253(3) . ? C1 C2 1.512(4) . ? C2 C3 1.396(3) . ? C2 C7 1.403(4) . ? C3 C4 1.366(4) . ? C3 H3 0.9500 . ? C4 C5 1.384(4) . ? C4 H4 0.9500 . ? C5 C6 1.383(4) . ? C5 H5 0.9500 . ? C6 C7 1.381(4) . ? C6 C8 1.499(4) . ? C7 H7 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.366(4) . ? C9 H9 0.9500 . ? C10 C11 1.392(4) . ? C10 H10 0.9500 . ? C11 C12 1.388(4) . ? C11 C14 1.485(4) . ? C12 C13 1.357(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C18 1.370(4) . ? C14 C15 1.390(4) . ? C15 C16 1.381(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.377(4) . ? C17 H17 0.9500 . ? C18 H18 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 C9 N1 C13 119.9(3) . . ? C9 N1 C8 121.2(2) . . ? C13 N1 C8 118.9(2) . . ? C16 N2 C17 116.2(3) . . ? O2 C1 O1 125.7(3) . . ? O2 C1 C2 116.4(2) . . ? O1 C1 C2 117.8(2) . . ? C3 C2 C7 118.2(3) . . ? C3 C2 C1 120.5(2) . . ? C7 C2 C1 121.3(2) . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 120.0(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 119.5(3) . . ? C7 C6 C8 120.5(3) . . ? C5 C6 C8 120.0(3) . . ? C6 C7 C2 120.7(3) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? C6 C8 N1 111.0(2) . . ? C6 C8 H8A 109.4 . . ? N1 C8 H8A 109.4 . . ? C6 C8 H8B 109.4 . . ? N1 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? N1 C9 C10 120.9(3) . . ? N1 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C11 121.2(3) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 115.8(3) . . ? C12 C11 C14 121.7(2) . . ? C10 C11 C14 122.4(2) . . ? C13 C12 C11 121.1(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? N1 C13 C12 121.0(3) . . ? N1 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C18 C14 C15 115.7(3) . . ? C18 C14 C11 121.9(2) . . ? C15 C14 C11 122.4(3) . . ? C16 C15 C14 120.0(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? N2 C16 C15 123.9(3) . . ? N2 C16 H16 118.1 . . ? C15 C16 H16 118.1 . . ? N2 C17 C18 123.2(3) . . ? N2 C17 H17 118.4 . . ? C18 C17 H17 118.4 . . ? C14 C18 C17 121.0(3) . . ? C14 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.513 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.091