# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name "Lyudmila Georgievna Kuz'mina" _publ_contact_author_address ; Institute of General & Inorganic Chemistry Moscow 119991 RUSSIAN FEDERATION ; _publ_contact_author_email KUZMINA@IGIC.RAS.RU _publ_section_title ; 4-(Styryl)quinolines: synthesis and study of [2+2]-photocycloaddition reactions in thin films and single crystals ; loop_ _publ_author_name L.G.Kuz'mina M.V.Alfimov A.Churakov S.Gromov J.A.K.Howard ; N.A.Lobova ; A.I.Vedernikov data_1 _database_code_depnum_ccdc_archive 'CCDC 630151' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 N O2' _chemical_formula_sum 'C19 H17 N O2' _chemical_formula_weight 291.34 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 'P 1 2(1)/c 1' 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 10.6020(3) _cell_length_b 10.9717(3) _cell_length_c 12.6859(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.022(2) _cell_angle_gamma 90.00 _cell_volume 1457.39(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120.0(2) _cell_measurement_reflns_used 6577 _cell_measurement_theta_min 2.468 _cell_measurement_theta_max 30.035 _exptl_crystal_description block _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART-1K' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11822 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3839 _reflns_number_gt 3181 _reflns_threshold_expression I>2\s(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^)+(0.0760P)^2^+0.2631P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3839 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.1209 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.09323(8) 0.93741(8) 0.10097(6) 0.0228(2) Uani 1 1 d . . . O2 O -0.00586(8) 1.05294(7) 0.24582(6) 0.02063(19) Uani 1 1 d . . . N1 N 0.59345(10) 0.88918(9) 0.91208(7) 0.0202(2) Uani 1 1 d . . . C1 C 0.48468(11) 0.94116(10) 0.86957(9) 0.0203(2) Uani 1 1 d . . . C2 C 0.43087(11) 0.93378(10) 0.76124(9) 0.0194(2) Uani 1 1 d . . . C3 C 0.49095(11) 0.86793(10) 0.69011(9) 0.0168(2) Uani 1 1 d . . . C4 C 0.60813(10) 0.80767(9) 0.73283(8) 0.0154(2) Uani 1 1 d . . . C5 C 0.68010(11) 0.73502(10) 0.67059(9) 0.0179(2) Uani 1 1 d . . . C6 C 0.79417(11) 0.68328(10) 0.71548(9) 0.0200(2) Uani 1 1 d . . . C7 C 0.84325(11) 0.70265(10) 0.82453(9) 0.0211(2) Uani 1 1 d . . . C8 C 0.77563(11) 0.77047(10) 0.88728(9) 0.0205(2) Uani 1 1 d . . . C9 C 0.65628(11) 0.82330(10) 0.84390(8) 0.0171(2) Uani 1 1 d . . . C10 C 0.43677(11) 0.85994(10) 0.57629(9) 0.0189(2) Uani 1 1 d . . . C11 C 0.34496(11) 0.93406(10) 0.52798(9) 0.0189(2) Uani 1 1 d . . . C12 C 0.28637(11) 0.93227(10) 0.41509(9) 0.0172(2) Uani 1 1 d . . . C13 C 0.33948(11) 0.87216(10) 0.33559(9) 0.0174(2) Uani 1 1 d . . . C14 C 0.27816(11) 0.87317(10) 0.22953(9) 0.0180(2) Uani 1 1 d . . . C15 C 0.16234(11) 0.93322(10) 0.20140(8) 0.0168(2) Uani 1 1 d . . . C16 C 0.10791(10) 0.99565(9) 0.28077(8) 0.0160(2) Uani 1 1 d . . . C17 C 0.17009(10) 0.99560(10) 0.38556(9) 0.0172(2) Uani 1 1 d . . . C18 C 0.15052(13) 0.88598(12) 0.01560(10) 0.0258(3) Uani 1 1 d . . . C19 C -0.06080(12) 1.12200(11) 0.32275(11) 0.0241(3) Uani 1 1 d . . . H1A H 0.4390(15) 0.9862(14) 0.9161(12) 0.024(4) Uiso 1 1 d . . . H2A H 0.3518(16) 0.9772(15) 0.7370(13) 0.033(4) Uiso 1 1 d . . . H5A H 0.6503(13) 0.7222(12) 0.5947(11) 0.017(3) Uiso 1 1 d . . . H6A H 0.8419(14) 0.6334(13) 0.6739(12) 0.023(4) Uiso 1 1 d . . . H7A H 0.9253(15) 0.6692(14) 0.8539(12) 0.028(4) Uiso 1 1 d . . . H8A H 0.8088(14) 0.7875(13) 0.9635(12) 0.022(3) Uiso 1 1 d . . . H10A H 0.4721(15) 0.7972(14) 0.5313(13) 0.032(4) Uiso 1 1 d . . . H11A H 0.3122(16) 1.0017(15) 0.5696(13) 0.034(4) Uiso 1 1 d . . . H13A H 0.4201(14) 0.8307(13) 0.3522(11) 0.022(3) Uiso 1 1 d . . . H14A H 0.3138(14) 0.8324(13) 0.1751(12) 0.022(3) Uiso 1 1 d . . . H19A H -0.0821(15) 1.0706(14) 0.3814(13) 0.029(4) Uiso 1 1 d . . . H19B H -0.1398(16) 1.1570(16) 0.2826(13) 0.035(4) Uiso 1 1 d . . . H19C H -0.0051(16) 1.1865(15) 0.3541(12) 0.031(4) Uiso 1 1 d . . . H18A H 0.1659(14) 0.7977(14) 0.0255(11) 0.023(4) Uiso 1 1 d . . . H18B H 0.2367(16) 0.9258(15) 0.0119(12) 0.031(4) Uiso 1 1 d . . . H18C H 0.0873(15) 0.9003(13) -0.0486(12) 0.024(4) Uiso 1 1 d . . . H17A H 0.1351(14) 1.0392(13) 0.4401(12) 0.023(4) 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 O1 0.0231(4) 0.0291(4) 0.0139(4) -0.0010(3) -0.0042(3) 0.0061(3) O2 0.0159(4) 0.0239(4) 0.0208(4) 0.0009(3) -0.0013(3) 0.0046(3) N1 0.0224(5) 0.0234(5) 0.0147(4) 0.0002(3) 0.0023(4) 0.0008(4) C1 0.0210(6) 0.0228(5) 0.0173(5) -0.0020(4) 0.0037(4) 0.0016(4) C2 0.0170(5) 0.0226(5) 0.0179(5) -0.0015(4) 0.0000(4) 0.0018(4) C3 0.0169(5) 0.0176(5) 0.0151(5) -0.0003(4) -0.0001(4) -0.0017(4) C4 0.0163(5) 0.0152(5) 0.0144(5) 0.0010(4) 0.0011(4) -0.0020(4) C5 0.0199(5) 0.0172(5) 0.0163(5) 0.0000(4) 0.0024(4) -0.0007(4) C6 0.0207(6) 0.0182(5) 0.0216(5) 0.0002(4) 0.0047(4) 0.0016(4) C7 0.0192(6) 0.0207(5) 0.0224(6) 0.0044(4) -0.0002(4) 0.0028(4) C8 0.0211(6) 0.0229(5) 0.0161(5) 0.0030(4) -0.0008(4) 0.0007(4) C9 0.0186(5) 0.0177(5) 0.0148(5) 0.0016(4) 0.0018(4) -0.0015(4) C10 0.0199(5) 0.0218(5) 0.0144(5) -0.0015(4) 0.0005(4) -0.0002(4) C11 0.0197(5) 0.0217(5) 0.0149(5) -0.0004(4) 0.0012(4) -0.0002(4) C12 0.0173(5) 0.0177(5) 0.0155(5) 0.0006(4) -0.0009(4) -0.0009(4) C13 0.0166(5) 0.0178(5) 0.0167(5) 0.0004(4) -0.0010(4) 0.0016(4) C14 0.0197(5) 0.0189(5) 0.0148(5) -0.0003(4) 0.0008(4) 0.0017(4) C15 0.0192(5) 0.0172(5) 0.0129(5) 0.0017(4) -0.0015(4) -0.0010(4) C16 0.0145(5) 0.0153(5) 0.0175(5) 0.0025(4) 0.0003(4) -0.0001(4) C17 0.0169(5) 0.0183(5) 0.0162(5) -0.0003(4) 0.0018(4) 0.0009(4) C18 0.0297(7) 0.0321(7) 0.0139(5) -0.0013(4) -0.0015(5) 0.0041(5) C19 0.0192(6) 0.0242(6) 0.0290(6) -0.0008(5) 0.0040(5) 0.0042(4) _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 C15 1.3672(12) . ? O1 C18 1.4375(15) . ? O2 C16 1.3707(13) . ? O2 C19 1.4298(14) . ? N1 C1 1.3232(15) . ? N1 C9 1.3766(14) . ? C1 C2 1.4052(15) . ? C1 H1A 0.957(16) . ? C2 C3 1.3864(15) . ? C2 H2A 0.971(17) . ? C3 C4 1.4363(15) . ? C3 C10 1.4706(14) . ? C4 C5 1.4248(15) . ? C4 C9 1.4316(14) . ? C5 C6 1.3759(16) . ? C5 H5A 0.975(14) . ? C6 C7 1.4155(16) . ? C6 H6A 0.958(15) . ? C7 C8 1.3713(17) . ? C7 H7A 0.963(16) . ? C8 C9 1.4219(15) . ? C8 H8A 0.994(15) . ? C10 C11 1.3405(16) . ? C10 H10A 1.003(16) . ? C11 C12 1.4691(15) . ? C11 H11A 1.003(17) . ? C12 C13 1.3954(15) . ? C12 C17 1.4136(15) . ? C13 C14 1.3995(14) . ? C13 H13A 0.962(15) . ? C14 C15 1.3900(15) . ? C14 H14A 0.950(15) . ? C15 C16 1.4136(15) . ? C16 C17 1.3882(15) . ? C17 H17A 0.962(15) . ? C18 H18A 0.987(15) . ? C18 H18B 1.020(17) . ? C18 H18C 0.983(15) . ? C19 H19A 0.987(16) . ? C19 H19B 0.987(17) . ? C19 H19C 0.967(17) . ? 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 C15 O1 C18 117.44(9) . . ? C16 O2 C19 117.02(9) . . ? C1 N1 C9 116.54(9) . . ? N1 C1 C2 124.61(10) . . ? N1 C1 H1A 117.6(9) . . ? C2 C1 H1A 117.8(9) . . ? C3 C2 C1 120.60(10) . . ? C3 C2 H2A 120.7(10) . . ? C1 C2 H2A 118.6(10) . . ? C2 C3 C4 116.92(10) . . ? C2 C3 C10 121.43(10) . . ? C4 C3 C10 121.64(10) . . ? C5 C4 C9 118.24(10) . . ? C5 C4 C3 123.72(10) . . ? C9 C4 C3 118.03(10) . . ? C6 C5 C4 120.91(10) . . ? C6 C5 H5A 118.5(8) . . ? C4 C5 H5A 120.6(8) . . ? C5 C6 C7 120.48(10) . . ? C5 C6 H6A 120.9(9) . . ? C7 C6 H6A 118.6(9) . . ? C8 C7 C6 120.22(10) . . ? C8 C7 H7A 120.3(9) . . ? C6 C7 H7A 119.5(9) . . ? C7 C8 C9 120.73(10) . . ? C7 C8 H8A 122.0(8) . . ? C9 C8 H8A 117.2(8) . . ? N1 C9 C8 117.37(9) . . ? N1 C9 C4 123.25(10) . . ? C8 C9 C4 119.37(10) . . ? C11 C10 C3 123.82(10) . . ? C11 C10 H10A 117.7(9) . . ? C3 C10 H10A 118.4(9) . . ? C10 C11 C12 127.10(10) . . ? C10 C11 H11A 119.6(9) . . ? C12 C11 H11A 113.2(9) . . ? C13 C12 C17 118.34(10) . . ? C13 C12 C11 123.65(10) . . ? C17 C12 C11 118.01(10) . . ? C12 C13 C14 120.79(10) . . ? C12 C13 H13A 120.7(8) . . ? C14 C13 H13A 118.5(9) . . ? C15 C14 C13 120.60(10) . . ? C15 C14 H14A 118.2(9) . . ? C13 C14 H14A 121.2(9) . . ? O1 C15 C14 125.31(10) . . ? O1 C15 C16 115.37(9) . . ? C14 C15 C16 119.32(9) . . ? O2 C16 C17 124.86(10) . . ? O2 C16 C15 115.38(9) . . ? C17 C16 C15 119.76(10) . . ? C16 C17 C12 121.16(10) . . ? C16 C17 H17A 120.7(9) . . ? C12 C17 H17A 118.2(9) . . ? O1 C18 H18A 111.7(9) . . ? O1 C18 H18B 110.7(9) . . ? H18A C18 H18B 107.1(12) . . ? O1 C18 H18C 104.3(9) . . ? H18A C18 H18C 109.9(12) . . ? H18B C18 H18C 113.2(12) . . ? O2 C19 H19A 112.2(9) . . ? O2 C19 H19B 104.9(10) . . ? H19A C19 H19B 109.5(13) . . ? O2 C19 H19C 112.4(10) . . ? H19A C19 H19C 107.8(13) . . ? H19B C19 H19C 110.0(14) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.374 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.048 #===END data_1_6 _database_code_depnum_ccdc_archive 'CCDC 630152' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H34 N2 O4' _chemical_formula_sum 'C38 H34 N2 O4' _chemical_formula_weight 582.67 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 2(1)/c 1' 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 10.7020(7) _cell_length_b 10.9624(7) _cell_length_c 12.5151(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.443(3) _cell_angle_gamma 90.00 _cell_volume 1452.35(16) _cell_formula_units_Z 2 _cell_measurement_temperature 120.0(2) _cell_measurement_reflns_used 2221 _cell_measurement_theta_min 2.482 _cell_measurement_theta_max 30.432 _exptl_crystal_description block _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11419 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3798 _reflns_number_gt 2903 _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^)+(0.0641P)^2^+0.7992P] 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 3798 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0864 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.1558 _refine_ls_wR_factor_gt 0.1466 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.004 _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 1.08637(15) 0.57528(14) 0.09928(11) 0.0382(4) Uani 1 1 d . A . O2 O 0.99231(12) 0.45626(12) 0.24719(10) 0.0267(3) Uani 1 1 d . . . N1 N 1.58954(17) 0.60793(15) 0.90747(13) 0.0309(4) Uani 1 1 d . A . C1 C 1.4831(2) 0.55581(18) 0.86378(18) 0.0321(5) Uani 1 1 d . . . C4 C 1.60886(16) 0.68775(15) 0.72685(14) 0.0217(4) Uani 1 1 d . . . C5 C 1.68007(17) 0.76150(15) 0.66472(14) 0.0223(4) Uani 1 1 d . A . C6 C 1.79072(17) 0.81514(16) 0.71041(14) 0.0228(4) Uani 1 1 d . . . C7 C 1.83791(19) 0.79476(17) 0.82050(15) 0.0262(4) Uani 1 1 d . A . C8 C 1.77044(19) 0.72664(17) 0.88325(15) 0.0277(4) Uani 1 1 d . . . C9 C 1.65352(17) 0.67348(16) 0.83903(14) 0.0229(4) Uani 1 1 d . A . C2 C 1.4320(10) 0.5630(9) 0.7632(7) 0.0227(14) Uani 0.657(5) 1 d P A 1 C3 C 1.4921(8) 0.6312(7) 0.6907(5) 0.0190(11) Uani 0.657(5) 1 d P A 1 C10 C 1.4371(3) 0.6395(2) 0.5761(2) 0.0187(7) Uani 0.657(5) 1 d P A 1 H10A H 1.471(3) 0.697(3) 0.532(2) 0.010(6) Uiso 0.657(5) 1 d P A 1 C11 C 1.3444(3) 0.5670(2) 0.5280(2) 0.0195(7) Uani 0.657(5) 1 d P A 1 H11A H 1.311(3) 0.505(3) 0.570(3) 0.031(9) Uiso 0.657(5) 1 d P A 1 C12 C 1.2852(7) 0.5708(6) 0.4147(5) 0.0162(9) Uani 0.657(5) 1 d P A 1 C2' C 1.442(2) 0.552(2) 0.7349(13) 0.027(3) Uani 0.343(5) 1 d P A 2 C3' C 1.5044(14) 0.6090(12) 0.6658(11) 0.019(2) Uani 0.343(5) 1 d P A 2 C10' C 1.4974(5) 0.5873(4) 0.5452(4) 0.0202(13) Uani 0.343(5) 1 d P . 2 H10C H 1.4941 0.6667 0.5055 0.024 Uiso 0.343(5) 1 calc PR A 2 C11' C 1.3936(5) 0.4987(4) 0.4896(4) 0.0195(13) Uani 0.343(5) 1 d P . 2 H11C H 1.3483 0.4575 0.5440 0.023 Uiso 0.343(5) 1 calc PR A 2 C12' C 1.3023(14) 0.5464(12) 0.3961(11) 0.019(2) Uani 0.343(5) 1 d P A 2 C13 C 1.33802(17) 0.62903(16) 0.32939(15) 0.0232(4) Uani 1 1 d . . . C14 C 1.27292(19) 0.63458(17) 0.22534(15) 0.0255(4) Uani 1 1 d . A . C15 C 1.15742(18) 0.57625(16) 0.19904(14) 0.0246(4) Uani 1 1 d . . . C16 C 1.10718(16) 0.51074(15) 0.27971(14) 0.0204(4) Uani 1 1 d . A . C17 C 1.17374(17) 0.50406(16) 0.38230(14) 0.0237(4) Uani 1 1 d . . . C18 C 1.1439(3) 0.6220(2) 0.01134(17) 0.0398(6) Uani 1 1 d . . . C19 C 0.94074(19) 0.38567(19) 0.32534(18) 0.0308(4) Uani 1 1 d . . . H1A H 1.437(2) 0.5129(19) 0.9106(17) 0.027(5) Uiso 1 1 d . . . H2A H 1.358(3) 0.522(2) 0.731(2) 0.053(8) Uiso 1 1 d . . . H5A H 1.651(2) 0.7777(19) 0.5905(17) 0.027(5) Uiso 1 1 d . . . H6A H 1.8371(19) 0.8658(18) 0.6681(16) 0.021(5) Uiso 1 1 d . . . H7A H 1.917(2) 0.827(2) 0.8502(17) 0.035(6) Uiso 1 1 d . . . H8A H 1.802(2) 0.7106(19) 0.9566(17) 0.029(5) Uiso 1 1 d . . . H13A H 1.420(2) 0.665(2) 0.3423(16) 0.028(5) Uiso 1 1 d . . . H14A H 1.306(2) 0.680(2) 0.1701(17) 0.028(5) Uiso 1 1 d . . . H17A H 1.142(2) 0.461(2) 0.4361(17) 0.029(5) Uiso 1 1 d . . . H18A H 1.083(2) 0.603(2) -0.0518(18) 0.032(6) Uiso 1 1 d . . . H18B H 1.158(2) 0.707(2) 0.0188(17) 0.032(6) Uiso 1 1 d . . . H18C H 1.230(3) 0.581(3) 0.008(2) 0.079(10) Uiso 1 1 d . . . H19A H 0.928(2) 0.436(2) 0.3891(19) 0.037(6) Uiso 1 1 d . . . H19B H 0.859(3) 0.352(2) 0.2869(19) 0.048(7) Uiso 1 1 d . . . H19C H 0.997(2) 0.310(2) 0.3490(18) 0.039(6) 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 O1 0.0443(9) 0.0453(9) 0.0219(7) 0.0019(6) -0.0059(6) -0.0208(7) O2 0.0199(7) 0.0290(7) 0.0293(7) -0.0010(5) -0.0024(5) -0.0051(5) N1 0.0383(10) 0.0259(8) 0.0313(8) -0.0041(6) 0.0150(7) -0.0072(7) C1 0.0312(11) 0.0236(9) 0.0454(12) 0.0004(8) 0.0185(9) -0.0032(8) C4 0.0187(8) 0.0180(8) 0.0276(9) 0.0005(6) 0.0000(7) 0.0018(6) C5 0.0245(9) 0.0192(8) 0.0222(8) 0.0015(6) 0.0008(7) 0.0008(7) C6 0.0241(9) 0.0189(8) 0.0261(9) -0.0006(7) 0.0056(7) -0.0018(7) C7 0.0251(10) 0.0239(9) 0.0286(9) -0.0043(7) 0.0004(7) -0.0058(7) C8 0.0338(10) 0.0277(9) 0.0206(8) -0.0041(7) 0.0009(7) -0.0055(8) C9 0.0262(9) 0.0184(8) 0.0254(9) -0.0035(7) 0.0078(7) -0.0007(7) C2 0.017(2) 0.021(2) 0.031(4) 0.002(2) 0.007(3) -0.0049(16) C3 0.024(2) 0.017(3) 0.014(2) -0.0018(16) -0.0025(17) 0.0019(18) C10 0.0184(13) 0.0211(13) 0.0172(12) -0.0022(10) 0.0043(10) -0.0004(11) C11 0.0196(13) 0.0208(13) 0.0186(12) -0.0019(10) 0.0045(10) 0.0008(10) C12 0.015(2) 0.016(2) 0.018(2) -0.0042(16) 0.0038(15) 0.0028(17) C2' 0.020(5) 0.031(5) 0.029(7) 0.003(5) 0.000(5) 0.006(3) C3' 0.018(4) 0.011(4) 0.028(6) -0.003(3) -0.003(4) -0.006(3) C10' 0.021(3) 0.016(2) 0.021(2) -0.0012(19) -0.004(2) 0.000(2) C11' 0.020(3) 0.018(2) 0.019(2) -0.0045(18) -0.0024(18) -0.0044(19) C12' 0.017(4) 0.021(5) 0.017(4) -0.010(3) 0.001(3) 0.011(3) C13 0.0178(9) 0.0195(8) 0.0311(9) 0.0007(7) -0.0004(7) -0.0003(7) C14 0.0305(10) 0.0229(8) 0.0235(9) -0.0018(7) 0.0059(7) -0.0046(7) C15 0.0284(10) 0.0226(8) 0.0215(8) -0.0036(7) -0.0006(7) -0.0019(7) C16 0.0168(8) 0.0174(8) 0.0262(8) -0.0053(6) 0.0002(6) 0.0000(6) C17 0.0226(9) 0.0240(9) 0.0238(9) 0.0034(7) 0.0008(7) -0.0038(7) C18 0.0558(16) 0.0406(12) 0.0208(9) -0.0012(8) -0.0017(10) -0.0152(11) C19 0.0227(10) 0.0298(10) 0.0393(11) 0.0013(8) 0.0028(8) -0.0038(8) _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 C15 1.363(2) . ? O1 C18 1.433(3) . ? O2 C16 1.374(2) . ? O2 C19 1.421(2) . ? N1 C1 1.320(3) . ? N1 C9 1.375(2) . ? C1 C2 1.299(10) . ? C1 C2' 1.608(17) . ? C4 C3 1.408(9) . ? C4 C5 1.419(2) . ? C4 C9 1.424(2) . ? C4 C3' 1.526(14) . ? C5 C6 1.370(3) . ? C6 C7 1.414(3) . ? C7 C8 1.365(3) . ? C8 C9 1.417(3) . ? C2 C3 1.403(11) . ? C3 C10 1.471(8) . ? C10 C11 1.342(4) . ? C11 C12 1.466(8) . ? C12 C17 1.407(8) . ? C12 C13 1.430(7) . ? C2' C3' 1.33(2) . ? C3' C10' 1.519(12) . ? C10' C11' 1.560(7) . ? C10' C11' 1.610(8) 3_866 ? C11' C12' 1.504(16) . ? C11' C10' 1.610(8) 3_866 ? C12' C13 1.326(16) . ? C12' C17 1.438(16) . ? C13 C14 1.385(3) . ? C14 C15 1.388(3) . ? C15 C16 1.408(2) . ? C16 C17 1.376(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 C15 O1 C18 117.12(16) . . ? C16 O2 C19 117.00(14) . . ? C1 N1 C9 116.54(17) . . ? C2 C1 N1 126.2(5) . . ? C2 C1 C2' 10.1(11) . . ? N1 C1 C2' 121.3(8) . . ? C3 C4 C5 126.7(3) . . ? C3 C4 C9 115.0(3) . . ? C5 C4 C9 118.26(16) . . ? C3 C4 C3' 16.3(5) . . ? C5 C4 C3' 117.4(6) . . ? C9 C4 C3' 123.2(6) . . ? C6 C5 C4 121.12(16) . . ? C5 C6 C7 120.15(17) . . ? C8 C7 C6 120.25(18) . . ? C7 C8 C9 120.78(17) . . ? N1 C9 C8 117.61(16) . . ? N1 C9 C4 123.09(16) . . ? C8 C9 C4 119.29(16) . . ? C1 C2 C3 119.4(9) . . ? C2 C3 C4 119.7(7) . . ? C2 C3 C10 120.5(8) . . ? C4 C3 C10 119.7(6) . . ? C11 C10 C3 124.4(4) . . ? C10 C11 C12 127.1(4) . . ? C17 C12 C13 115.3(5) . . ? C17 C12 C11 119.5(5) . . ? C13 C12 C11 124.9(5) . . ? C3' C2' C1 123.6(18) . . ? C2' C3' C10' 128.3(13) . . ? C2' C3' C4 110.0(13) . . ? C10' C3' C4 120.8(10) . . ? C3' C10' C11' 117.9(7) . . ? C3' C10' C11' 115.4(6) . 3_866 ? C11' C10' C11' 90.7(4) . 3_866 ? C12' C11' C10' 118.0(7) . . ? C12' C11' C10' 114.0(5) . 3_866 ? C10' C11' C10' 89.3(4) . 3_866 ? C13 C12' C17 120.3(11) . . ? C13 C12' C11' 120.9(11) . . ? C17 C12' C11' 118.8(11) . . ? C12' C13 C14 118.1(7) . . ? C12' C13 C12 16.8(4) . . ? C14 C13 C12 121.5(3) . . ? C13 C14 C15 120.69(17) . . ? O1 C15 C14 125.35(17) . . ? O1 C15 C16 115.61(16) . . ? C14 C15 C16 119.04(16) . . ? O2 C16 C17 124.87(16) . . ? O2 C16 C15 115.37(15) . . ? C17 C16 C15 119.76(16) . . ? C16 C17 C12 122.8(3) . . ? C16 C17 C12' 116.8(6) . . ? C12 C17 C12' 16.7(4) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.397 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.054 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 630153' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C21 H22 N O2)1+, 0.5(C6 H6), (Cl O4)1-' _chemical_formula_sum 'C24 H25 Cl N O6' _chemical_formula_weight 458.90 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 'P 1 2(1)/n 1' 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 7.0340(5) _cell_length_b 21.0718(14) _cell_length_c 14.6964(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.3050(10) _cell_angle_gamma 90.00 _cell_volume 2172.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120.0(2) _cell_measurement_reflns_used 6916 _cell_measurement_theta_min 2.381 _cell_measurement_theta_max 29.649 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 0.218 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART-1K' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14637 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 28.99 _reflns_number_total 5628 _reflns_number_gt 4185 _reflns_threshold_expression I>2\s(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^)+(0.0865P)^2^+0.2177P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5628 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1311 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _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 0.54674(6) 0.607359(18) 0.23579(3) 0.02541(12) Uani 1 1 d . . . O1' O 0.5474(2) 0.61719(7) 0.13900(9) 0.0356(3) Uani 1 1 d . . . O2' O 0.7063(2) 0.56779(6) 0.26692(10) 0.0372(3) Uani 1 1 d . . . O3' O 0.5613(2) 0.66755(6) 0.28209(9) 0.0380(3) Uani 1 1 d . . . O4' O 0.3722(2) 0.57640(7) 0.25516(11) 0.0450(4) Uani 1 1 d . . . O1 O 0.4803(2) 0.63060(6) 0.79239(9) 0.0327(3) Uani 1 1 d . . . O2 O 0.5226(2) 0.74251(6) 0.72937(9) 0.0334(3) Uani 1 1 d . . . N1 N 0.05399(19) 0.35984(7) 0.28565(9) 0.0228(3) Uani 1 1 d . . . C1 C 0.4584(3) 0.56921(9) 0.83111(14) 0.0333(4) Uani 1 1 d . . . C2 C 0.5345(3) 0.80697(9) 0.69814(15) 0.0354(4) Uani 1 1 d . . . C3 C 0.4673(2) 0.69788(8) 0.66568(11) 0.0235(3) Uani 1 1 d . . . C4 C 0.4358(2) 0.70880(8) 0.57310(12) 0.0249(3) Uani 1 1 d . . . C5 C 0.3812(2) 0.65931(8) 0.51426(12) 0.0239(3) Uani 1 1 d . . . C6 C 0.3531(2) 0.59820(8) 0.54711(11) 0.0222(3) Uani 1 1 d . . . C7 C 0.3860(2) 0.58685(8) 0.64170(11) 0.0219(3) Uani 1 1 d . . . C8 C 0.4427(2) 0.63606(8) 0.70010(11) 0.0234(3) Uani 1 1 d . . . C9 C 0.2849(2) 0.54978(8) 0.48151(12) 0.0253(3) Uani 1 1 d . . . C10 C 0.2318(2) 0.49000(8) 0.49864(12) 0.0244(3) Uani 1 1 d . . . C11 C 0.1651(2) 0.44527(8) 0.42773(11) 0.0222(3) Uani 1 1 d . . . C19 C 0.1300(2) 0.46458(8) 0.33752(12) 0.0262(3) Uani 1 1 d . . . C18 C 0.0783(2) 0.42175(8) 0.26945(12) 0.0260(3) Uani 1 1 d . . . C17 C 0.0753(2) 0.33726(8) 0.37456(10) 0.0205(3) Uani 1 1 d . . . C16 C 0.0411(2) 0.27267(8) 0.39254(12) 0.0245(3) Uani 1 1 d . . . C15 C 0.0603(2) 0.25055(8) 0.48055(12) 0.0272(4) Uani 1 1 d . . . C14 C 0.1134(2) 0.29183(8) 0.55351(12) 0.0267(3) Uani 1 1 d . . . C13 C 0.1483(2) 0.35443(8) 0.53680(11) 0.0242(3) Uani 1 1 d . . . C12 C 0.1303(2) 0.37978(7) 0.44726(11) 0.0205(3) Uani 1 1 d . . . C20 C 0.0044(3) 0.31392(9) 0.20979(12) 0.0312(4) Uani 1 1 d . . . C21 C 0.0029(4) 0.34161(11) 0.11547(14) 0.0449(5) Uani 1 1 d . . . C1S C 1.1769(3) 0.48342(11) -0.02646(17) 0.0435(5) Uani 1 1 d . . . C2S C 1.1606(3) 0.52280(10) 0.04727(16) 0.0450(5) Uani 1 1 d . . . C3S C 0.9851(4) 0.53914(10) 0.07391(14) 0.0450(6) Uani 1 1 d . . . H4A H 0.452(3) 0.7507(11) 0.5508(16) 0.037(6) Uiso 1 1 d . . . H5A H 0.362(3) 0.6665(9) 0.4527(14) 0.025(5) Uiso 1 1 d . . . H7A H 0.372(2) 0.5457(9) 0.6667(12) 0.017(4) Uiso 1 1 d . . . H9A H 0.289(3) 0.5671(11) 0.4122(17) 0.045(6) Uiso 1 1 d . . . H10A H 0.252(3) 0.4733(11) 0.5610(16) 0.040(6) Uiso 1 1 d . . . H19A H 0.143(3) 0.5068(11) 0.3234(15) 0.037(6) Uiso 1 1 d . . . H18A H 0.053(3) 0.4368(10) 0.2073(14) 0.024(5) Uiso 1 1 d . . . H16A H 0.009(3) 0.2474(10) 0.3426(15) 0.030(5) Uiso 1 1 d . . . H15A H 0.030(3) 0.2072(12) 0.4924(15) 0.035(6) Uiso 1 1 d . . . H14A H 0.127(3) 0.2769(10) 0.6131(15) 0.028(5) Uiso 1 1 d . . . H13A H 0.180(3) 0.3800(11) 0.5835(16) 0.037(6) Uiso 1 1 d . . . H21A H -0.032(4) 0.3040(16) 0.070(2) 0.077(9) Uiso 1 1 d . . . H21B H -0.107(4) 0.3774(13) 0.1065(18) 0.052(7) Uiso 1 1 d . . . H21C H 0.143(4) 0.3542(13) 0.1003(18) 0.057(8) Uiso 1 1 d . . . H2A H 0.409(3) 0.8216(10) 0.6732(14) 0.031(5) Uiso 1 1 d . . . H20A H 0.112(4) 0.2807(13) 0.2043(17) 0.052(7) Uiso 1 1 d . . . H20B H -0.122(3) 0.2991(10) 0.2225(14) 0.032(5) Uiso 1 1 d . . . H1A H 0.327(3) 0.5513(11) 0.8183(16) 0.039(6) Uiso 1 1 d . . . H1B H 0.553(3) 0.5414(11) 0.8093(16) 0.039(6) Uiso 1 1 d . . . H2B H 0.630(3) 0.8110(11) 0.6535(16) 0.038(6) Uiso 1 1 d . . . H1C H 0.492(3) 0.5739(11) 0.8925(16) 0.033(6) Uiso 1 1 d . . . H2C H 0.571(3) 0.8317(12) 0.7505(17) 0.046(7) Uiso 1 1 d . . . H2S H 1.271(4) 0.5404(13) 0.0798(19) 0.058(8) Uiso 1 1 d . . . H1S H 1.297(4) 0.4712(14) -0.0422(19) 0.062(8) Uiso 1 1 d . . . H3S H 0.996(4) 0.5685(17) 0.122(2) 0.084(10) 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 0.0341(2) 0.01968(19) 0.02209(19) 0.00067(14) -0.00018(14) -0.00155(15) O1' 0.0477(8) 0.0373(7) 0.0216(6) 0.0020(5) 0.0015(5) -0.0003(6) O2' 0.0463(8) 0.0270(6) 0.0367(8) -0.0021(6) -0.0081(6) 0.0079(6) O3' 0.0592(9) 0.0200(6) 0.0330(7) -0.0056(5) -0.0095(6) 0.0039(6) O4' 0.0438(8) 0.0441(9) 0.0484(9) 0.0024(7) 0.0126(7) -0.0112(7) O1 0.0523(8) 0.0222(6) 0.0230(6) 0.0018(5) -0.0015(5) -0.0042(5) O2 0.0512(8) 0.0199(6) 0.0293(7) -0.0035(5) 0.0032(6) -0.0044(5) N1 0.0221(7) 0.0250(7) 0.0212(7) -0.0015(5) 0.0018(5) -0.0009(5) C1 0.0465(11) 0.0268(9) 0.0262(9) 0.0060(7) -0.0001(8) -0.0024(8) C2 0.0468(12) 0.0199(8) 0.0401(11) -0.0029(7) 0.0075(9) -0.0050(8) C3 0.0253(8) 0.0191(7) 0.0265(8) -0.0031(6) 0.0042(6) -0.0010(6) C4 0.0268(8) 0.0209(8) 0.0273(8) 0.0024(6) 0.0041(6) -0.0006(6) C5 0.0224(8) 0.0269(8) 0.0225(8) 0.0010(6) 0.0026(6) 0.0007(6) C6 0.0194(7) 0.0221(7) 0.0255(8) -0.0021(6) 0.0037(6) 0.0009(6) C7 0.0214(7) 0.0177(7) 0.0270(8) 0.0004(6) 0.0038(6) 0.0013(6) C8 0.0246(8) 0.0230(8) 0.0229(8) 0.0010(6) 0.0028(6) 0.0013(6) C9 0.0233(8) 0.0260(8) 0.0266(8) -0.0027(6) 0.0021(6) 0.0005(6) C10 0.0230(8) 0.0256(8) 0.0247(8) -0.0020(6) 0.0025(6) 0.0006(6) C11 0.0197(7) 0.0222(8) 0.0251(8) -0.0032(6) 0.0037(6) 0.0010(6) C19 0.0280(8) 0.0234(8) 0.0272(8) 0.0015(7) 0.0025(6) -0.0018(6) C18 0.0253(8) 0.0296(9) 0.0232(8) 0.0025(7) 0.0028(6) -0.0020(6) C17 0.0166(7) 0.0247(8) 0.0206(7) -0.0013(6) 0.0026(5) 0.0020(6) C16 0.0248(8) 0.0228(8) 0.0257(8) -0.0047(6) 0.0009(6) 0.0008(6) C15 0.0278(8) 0.0229(8) 0.0307(9) 0.0008(7) 0.0007(7) 0.0009(6) C14 0.0284(8) 0.0276(8) 0.0237(8) 0.0028(6) -0.0006(6) 0.0012(7) C13 0.0241(8) 0.0263(8) 0.0219(8) -0.0031(6) -0.0004(6) 0.0017(6) C12 0.0174(7) 0.0227(7) 0.0214(7) -0.0017(6) 0.0016(5) 0.0031(6) C20 0.0384(10) 0.0320(9) 0.0232(8) -0.0069(7) 0.0023(7) -0.0042(8) C21 0.0686(16) 0.0400(12) 0.0262(10) -0.0059(8) 0.0036(9) -0.0032(11) C1S 0.0416(12) 0.0395(11) 0.0517(13) 0.0186(10) 0.0179(10) 0.0105(9) C2S 0.0493(12) 0.0327(10) 0.0494(13) 0.0104(9) -0.0210(10) -0.0144(9) C3S 0.0838(18) 0.0251(9) 0.0261(10) -0.0018(8) 0.0039(10) 0.0074(10) _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 O4' 1.4375(15) . ? Cl1 O1' 1.4378(13) . ? Cl1 O3' 1.4393(13) . ? Cl1 O2' 1.4449(13) . ? O1 C8 1.367(2) . ? O1 C1 1.426(2) . ? O2 C3 1.363(2) . ? O2 C2 1.438(2) . ? N1 C18 1.339(2) . ? N1 C17 1.388(2) . ? N1 C20 1.497(2) . ? C3 C4 1.381(2) . ? C3 C8 1.413(2) . ? C4 C5 1.390(2) . ? C5 C6 1.395(2) . ? C6 C7 1.412(2) . ? C6 C9 1.460(2) . ? C7 C8 1.385(2) . ? C9 C10 1.343(2) . ? C10 C11 1.456(2) . ? C11 C19 1.391(2) . ? C11 C12 1.434(2) . ? C19 C18 1.376(2) . ? C17 C16 1.410(2) . ? C17 C12 1.425(2) . ? C16 C15 1.372(2) . ? C15 C14 1.409(2) . ? C14 C13 1.367(2) . ? C13 C12 1.417(2) . ? C20 C21 1.503(3) . ? C1S C3S 1.375(3) 3_765 ? C1S C2S 1.376(4) . ? C2S C3S 1.367(4) . ? C3S C1S 1.375(3) 3_765 ? 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 O4' Cl1 O1' 109.11(9) . . ? O4' Cl1 O3' 109.73(9) . . ? O1' Cl1 O3' 109.60(8) . . ? O4' Cl1 O2' 109.28(9) . . ? O1' Cl1 O2' 109.65(9) . . ? O3' Cl1 O2' 109.45(8) . . ? C8 O1 C1 116.97(14) . . ? C3 O2 C2 116.94(15) . . ? C18 N1 C17 119.66(14) . . ? C18 N1 C20 121.51(14) . . ? C17 N1 C20 118.83(14) . . ? O2 C3 C4 125.32(15) . . ? O2 C3 C8 115.26(15) . . ? C4 C3 C8 119.42(15) . . ? C3 C4 C5 120.28(15) . . ? C4 C5 C6 121.13(15) . . ? C5 C6 C7 118.69(15) . . ? C5 C6 C9 117.70(15) . . ? C7 C6 C9 123.58(15) . . ? C8 C7 C6 120.09(15) . . ? O1 C8 C7 125.23(15) . . ? O1 C8 C3 114.39(14) . . ? C7 C8 C3 120.38(15) . . ? C10 C9 C6 127.87(16) . . ? C9 C10 C11 123.51(16) . . ? C19 C11 C12 116.83(15) . . ? C19 C11 C10 121.15(15) . . ? C12 C11 C10 122.02(15) . . ? C18 C19 C11 121.30(16) . . ? N1 C18 C19 122.68(16) . . ? N1 C17 C16 119.94(14) . . ? N1 C17 C12 119.62(14) . . ? C16 C17 C12 120.43(15) . . ? C15 C16 C17 119.89(15) . . ? C16 C15 C14 120.61(16) . . ? C13 C14 C15 119.99(16) . . ? C14 C13 C12 121.71(16) . . ? C13 C12 C17 117.35(15) . . ? C13 C12 C11 122.94(15) . . ? C17 C12 C11 119.71(14) . . ? N1 C20 C21 114.89(16) . . ? C3S C1S C2S 119.5(2) 3_765 . ? C3S C2S C1S 120.5(2) . . ? C2S C3S C1S 120.0(2) . 3_765 ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 28.99 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.548 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.054 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 630154' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H33 N O6, C H2 Cl2, H2 O' _chemical_formula_sum 'C28 H35 Cl2 N O7' _chemical_formula_weight 568.47 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 'P 1 2(1)/c 1' 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 14.135(4) _cell_length_b 7.983(2) _cell_length_c 25.020(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.855(10) _cell_angle_gamma 90.00 _cell_volume 2772.7(14) _cell_formula_units_Z 4 _cell_measurement_temperature 120.0(2) _cell_measurement_reflns_used 627 _cell_measurement_theta_min 2.935 _cell_measurement_theta_max 29.600 _exptl_crystal_description plate _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.281 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART-6K' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18483 _diffrn_reflns_av_R_equivalents 0.2731 _diffrn_reflns_av_sigmaI/netI 0.3642 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 29.00 _reflns_number_total 7330 _reflns_number_gt 2222 _reflns_threshold_expression I>2\s(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^)+(0.1871P)^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 0.061(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7330 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3390 _refine_ls_R_factor_gt 0.1576 _refine_ls_wR_factor_ref 0.4553 _refine_ls_wR_factor_gt 0.4168 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 -0.2202(5) 1.0608(9) 0.1718(3) 0.0279(16) Uani 1 1 d . . . O2 O -0.4120(5) 1.0097(9) 0.1972(3) 0.0348(18) Uani 1 1 d . . . O3 O -0.4042(5) 0.9131(8) 0.3116(3) 0.0295(17) Uani 1 1 d . . . O4 O -0.2136(5) 0.8464(9) 0.3751(3) 0.0335(18) Uani 1 1 d . . . O5 O -0.0483(5) 0.7949(9) 0.3262(3) 0.0324(17) Uani 1 1 d . . . O6 O -0.0623(5) 0.9282(8) 0.2221(2) 0.0222(15) Uani 1 1 d . . . N1 N 0.3021(7) 0.5350(12) -0.0441(4) 0.040(2) Uani 1 1 d . . . C1 C 0.2119(10) 0.4991(15) -0.0468(5) 0.043(3) Uani 1 1 d . . . H1B H 0.1826 0.4256 -0.0750 0.052 Uiso 1 1 calc R . . C2 C 0.1530(8) 0.5611(13) -0.0107(4) 0.031(2) Uani 1 1 d . . . H2A H 0.0883 0.5239 -0.0144 0.037 Uiso 1 1 calc R . . C3 C 0.1883(8) 0.6717(13) 0.0284(4) 0.030(2) Uani 1 1 d . . . C4 C 0.2877(8) 0.7245(14) 0.0328(4) 0.035(3) Uani 1 1 d . . . C5 C 0.3338(7) 0.8421(13) 0.0722(4) 0.029(2) Uani 1 1 d . . . H5A H 0.2985 0.8940 0.0964 0.035 Uiso 1 1 calc R . . C6 C 0.4283(9) 0.8797(15) 0.0751(5) 0.047(3) Uani 1 1 d . . . H6A H 0.4594 0.9561 0.1019 0.056 Uiso 1 1 calc R . . C7 C 0.4813(8) 0.8040(16) 0.0377(5) 0.046(3) Uani 1 1 d . . . H7A H 0.5474 0.8316 0.0403 0.055 Uiso 1 1 calc R . . C8 C 0.4409(8) 0.6972(17) -0.0003(5) 0.046(3) Uani 1 1 d . . . H8A H 0.4770 0.6518 -0.0252 0.056 Uiso 1 1 calc R . . C9 C 0.3421(7) 0.6508(13) -0.0034(4) 0.030(2) Uani 1 1 d . . . C10 C 0.1294(8) 0.7450(13) 0.0645(4) 0.031(2) Uani 1 1 d . . . H10A H 0.1570 0.7586 0.1019 0.037 Uiso 1 1 calc R . . C11 C 0.0382(7) 0.7937(13) 0.0469(4) 0.025(2) Uani 1 1 d . . . H11A H 0.0136 0.7826 0.0091 0.030 Uiso 1 1 calc R . . C12 C -0.0284(8) 0.8629(13) 0.0805(4) 0.032(3) Uani 1 1 d . . . C13 C -0.1149(8) 0.9353(13) 0.0540(4) 0.033(3) Uani 1 1 d . . . H13A H -0.1298 0.9336 0.0153 0.039 Uiso 1 1 calc R . . C14 C -0.1798(8) 1.0097(13) 0.0823(4) 0.031(2) Uani 1 1 d . . . H14A H -0.2351 1.0668 0.0634 0.037 Uiso 1 1 calc R . . C15 C -0.1624(7) 0.9988(12) 0.1384(4) 0.027(2) Uani 1 1 d . . . C16 C -0.0731(7) 0.9274(12) 0.1661(3) 0.022(2) Uani 1 1 d . . . C17 C -0.0097(7) 0.8567(12) 0.1376(4) 0.028(2) Uani 1 1 d . . . H17A H 0.0470 0.8034 0.1565 0.034 Uiso 1 1 calc R . . C18 C -0.3112(7) 1.1351(14) 0.1436(4) 0.031(2) Uani 1 1 d . . . H18A H -0.3442 1.0582 0.1150 0.037 Uiso 1 1 calc R . . H18B H -0.2988 1.2424 0.1263 0.037 Uiso 1 1 calc R . . C19 C -0.3726(8) 1.1638(13) 0.1860(4) 0.033(2) Uani 1 1 d . . . H19A H -0.3328 1.2104 0.2195 0.039 Uiso 1 1 calc R . . H19B H -0.4246 1.2446 0.1722 0.039 Uiso 1 1 calc R . . C20 C -0.4858(8) 1.0288(15) 0.2279(5) 0.042(3) Uani 1 1 d . . . H20A H -0.5272 0.9277 0.2225 0.050 Uiso 1 1 calc R . . H20B H -0.5263 1.1255 0.2132 0.050 Uiso 1 1 calc R . . C21 C -0.4521(8) 1.0548(14) 0.2880(4) 0.036(3) Uani 1 1 d . . . H21A H -0.4083 1.1526 0.2941 0.043 Uiso 1 1 calc R . . H21B H -0.5082 1.0783 0.3053 0.043 Uiso 1 1 calc R . . C22 C -0.3778(8) 0.9303(14) 0.3684(4) 0.035(3) Uani 1 1 d . . . H22A H -0.4349 0.9148 0.3855 0.042 Uiso 1 1 calc R . . H22B H -0.3515 1.0438 0.3777 0.042 Uiso 1 1 calc R . . C23 C -0.3013(8) 0.7976(15) 0.3898(5) 0.037(3) Uani 1 1 d . . . H23A H -0.2930 0.7889 0.4299 0.044 Uiso 1 1 calc R . . H23B H -0.3216 0.6869 0.3739 0.044 Uiso 1 1 calc R . . C24 C -0.1367(7) 0.7390(13) 0.3960(4) 0.031(2) Uani 1 1 d . . . H24A H -0.1488 0.6260 0.3798 0.037 Uiso 1 1 calc R . . H24B H -0.1304 0.7289 0.4359 0.037 Uiso 1 1 calc R . . C25 C -0.0456(7) 0.8099(14) 0.3824(4) 0.031(2) Uani 1 1 d . . . H25A H -0.0393 0.9293 0.3932 0.037 Uiso 1 1 calc R . . H25B H 0.0107 0.7486 0.4027 0.037 Uiso 1 1 calc R . . C26 C 0.0284(7) 0.8838(13) 0.3106(4) 0.027(2) Uani 1 1 d . . . H26A H 0.0905 0.8437 0.3319 0.033 Uiso 1 1 calc R . . H26B H 0.0222 1.0046 0.3181 0.033 Uiso 1 1 calc R . . C27 C 0.0262(7) 0.8573(14) 0.2507(4) 0.031(2) Uani 1 1 d . . . H27A H 0.0819 0.9134 0.2396 0.037 Uiso 1 1 calc R . . H27B H 0.0290 0.7363 0.2426 0.037 Uiso 1 1 calc R . . Cl1 Cl -0.2624(2) 0.5144(3) 0.27921(12) 0.0393(8) Uani 1 1 d . . . Cl2 Cl -0.2867(2) 0.6338(4) 0.16807(12) 0.0481(9) Uani 1 1 d . . . O1S O -0.1905(5) 1.1171(10) 0.3008(3) 0.0383(19) Uani 1 1 d . . . C1S C -0.2618(9) 0.6933(13) 0.2366(5) 0.040(3) Uani 1 1 d . . . H1SA H -0.3108 0.7747 0.2437 0.048 Uiso 1 1 calc R . . H1SB H -0.1979 0.7484 0.2450 0.048 Uiso 1 1 calc R . . H1S H -0.1807 1.0845 0.2679 0.050 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 O1 0.025(4) 0.030(4) 0.029(4) -0.002(3) 0.006(3) 0.004(3) O2 0.037(4) 0.024(4) 0.043(4) -0.005(4) 0.007(4) 0.004(3) O3 0.033(4) 0.026(4) 0.029(4) 0.007(3) 0.003(3) 0.006(3) O4 0.029(4) 0.035(4) 0.038(4) 0.005(4) 0.010(3) 0.000(3) O5 0.046(5) 0.029(4) 0.025(4) -0.004(3) 0.013(3) 0.000(4) O6 0.025(4) 0.025(3) 0.018(3) 0.001(3) 0.007(3) -0.004(3) N1 0.050(6) 0.045(6) 0.033(5) 0.010(5) 0.029(5) 0.009(5) C1 0.065(9) 0.032(6) 0.032(6) 0.000(6) 0.006(6) -0.004(6) C2 0.038(6) 0.028(5) 0.025(5) -0.004(5) 0.004(5) 0.004(5) C3 0.041(6) 0.025(5) 0.027(5) 0.002(5) 0.016(5) -0.005(5) C4 0.046(7) 0.029(6) 0.029(6) 0.007(5) 0.007(5) -0.005(5) C5 0.031(6) 0.026(5) 0.032(6) -0.008(5) 0.007(5) -0.001(5) C6 0.051(8) 0.033(6) 0.056(8) -0.020(6) 0.008(6) -0.013(6) C7 0.029(6) 0.050(8) 0.058(8) 0.004(7) 0.005(6) -0.003(6) C8 0.026(6) 0.063(8) 0.054(7) -0.018(7) 0.018(6) 0.003(6) C9 0.033(6) 0.029(6) 0.031(5) 0.002(5) 0.013(5) 0.006(5) C10 0.045(7) 0.027(5) 0.023(5) 0.006(5) 0.014(5) -0.001(5) C11 0.029(6) 0.030(5) 0.021(5) -0.003(4) 0.015(4) -0.003(4) C12 0.046(7) 0.028(5) 0.032(5) -0.005(5) 0.030(5) -0.005(5) C13 0.044(7) 0.024(5) 0.031(6) -0.012(5) 0.010(5) -0.010(5) C14 0.039(6) 0.032(6) 0.021(5) 0.008(5) 0.007(5) 0.006(5) C15 0.033(6) 0.021(5) 0.029(5) 0.001(5) 0.009(5) -0.005(5) C16 0.034(6) 0.021(5) 0.009(4) 0.003(4) 0.004(4) -0.001(4) C17 0.033(6) 0.021(5) 0.029(5) 0.002(5) 0.000(4) 0.007(4) C18 0.032(6) 0.030(6) 0.032(5) -0.002(5) 0.011(5) 0.002(5) C19 0.036(6) 0.026(6) 0.036(6) -0.003(5) 0.007(5) 0.001(5) C20 0.031(6) 0.036(6) 0.067(8) 0.004(6) 0.030(6) 0.001(5) C21 0.045(7) 0.024(5) 0.042(6) 0.005(5) 0.018(5) 0.012(5) C22 0.036(6) 0.032(6) 0.042(6) 0.000(5) 0.019(5) 0.000(5) C23 0.036(6) 0.037(6) 0.039(6) 0.005(5) 0.011(5) -0.001(5) C24 0.030(6) 0.035(6) 0.029(6) 0.009(5) 0.012(5) 0.003(5) C25 0.025(5) 0.039(6) 0.028(5) -0.005(5) 0.001(4) 0.005(5) C26 0.035(6) 0.026(5) 0.024(5) 0.003(4) 0.011(4) 0.000(4) C27 0.035(6) 0.034(6) 0.023(5) -0.001(5) 0.004(4) 0.002(5) Cl1 0.0397(16) 0.0346(15) 0.0473(17) -0.0028(14) 0.0178(13) -0.0020(13) Cl2 0.067(2) 0.0386(16) 0.0450(17) -0.0048(15) 0.0274(15) -0.0078(15) O1S 0.042(5) 0.040(5) 0.033(4) 0.004(4) 0.008(3) -0.005(4) C1S 0.052(7) 0.021(5) 0.050(7) -0.007(5) 0.018(6) 0.001(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 C15 1.366(11) . ? O1 C18 1.470(12) . ? O2 C19 1.401(12) . ? O2 C20 1.415(12) . ? O3 C21 1.392(12) . ? O3 C22 1.408(12) . ? O4 C24 1.406(12) . ? O4 C23 1.414(12) . ? O5 C25 1.405(12) . ? O5 C26 1.410(12) . ? O6 C16 1.382(10) . ? O6 C27 1.435(12) . ? N1 C1 1.297(15) . ? N1 C9 1.413(14) . ? C1 C2 1.427(15) . ? C2 C3 1.342(14) . ? C3 C4 1.451(15) . ? C3 C10 1.461(14) . ? C4 C9 1.420(14) . ? C4 C5 1.428(14) . ? C5 C6 1.357(15) . ? C6 C7 1.438(17) . ? C7 C8 1.323(17) . ? C8 C9 1.433(15) . ? C10 C11 1.340(14) . ? C11 C12 1.481(13) . ? C12 C13 1.402(16) . ? C12 C17 1.405(14) . ? C13 C14 1.394(14) . ? C14 C15 1.381(13) . ? C15 C16 1.439(14) . ? C16 C17 1.367(13) . ? C18 C19 1.508(14) . ? C20 C21 1.504(16) . ? C22 C23 1.536(15) . ? C24 C25 1.502(14) . ? C26 C27 1.508(13) . ? Cl1 C1S 1.783(12) . ? Cl2 C1S 1.750(12) . ? 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 C15 O1 C18 115.0(7) . . ? C19 O2 C20 112.2(8) . . ? C21 O3 C22 111.4(8) . . ? C24 O4 C23 112.9(8) . . ? C25 O5 C26 110.9(8) . . ? C16 O6 C27 115.0(7) . . ? C1 N1 C9 115.9(9) . . ? N1 C1 C2 125.2(11) . . ? C3 C2 C1 120.5(11) . . ? C2 C3 C4 117.9(10) . . ? C2 C3 C10 122.5(10) . . ? C4 C3 C10 119.6(10) . . ? C9 C4 C5 118.8(10) . . ? C9 C4 C3 117.6(10) . . ? C5 C4 C3 123.6(10) . . ? C6 C5 C4 120.0(10) . . ? C5 C6 C7 120.0(11) . . ? C8 C7 C6 122.1(11) . . ? C7 C8 C9 119.4(11) . . ? N1 C9 C4 122.7(10) . . ? N1 C9 C8 117.5(9) . . ? C4 C9 C8 119.8(10) . . ? C11 C10 C3 122.6(10) . . ? C10 C11 C12 126.7(10) . . ? C13 C12 C17 118.5(9) . . ? C13 C12 C11 118.5(9) . . ? C17 C12 C11 123.1(10) . . ? C14 C13 C12 122.3(10) . . ? C15 C14 C13 118.8(10) . . ? O1 C15 C14 125.9(9) . . ? O1 C15 C16 114.9(8) . . ? C14 C15 C16 119.1(9) . . ? C17 C16 O6 125.0(9) . . ? C17 C16 C15 121.0(8) . . ? O6 C16 C15 113.9(8) . . ? C16 C17 C12 120.0(9) . . ? O1 C18 C19 107.0(8) . . ? O2 C19 C18 108.1(9) . . ? O2 C20 C21 115.5(10) . . ? O3 C21 C20 110.4(9) . . ? O3 C22 C23 108.7(8) . . ? O4 C23 C22 108.3(9) . . ? O4 C24 C25 108.7(8) . . ? O5 C25 C24 109.4(8) . . ? O5 C26 C27 109.3(8) . . ? O6 C27 C26 107.0(8) . . ? Cl2 C1S Cl1 110.2(6) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.325 _refine_diff_density_min -0.599 _refine_diff_density_rms 0.170 #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 630155' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H34 N2 O4' _chemical_formula_sum 'C38 H34 N2 O4' _chemical_formula_weight 582.67 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 2(1)/c 1' 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 10.9855(12) _cell_length_b 10.8828(12) _cell_length_c 12.2120(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.282(5) _cell_angle_gamma 90.00 _cell_volume 1444.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120.0(2) _cell_measurement_reflns_used 1097 _cell_measurement_theta_min 2.649 _cell_measurement_theta_max 21.863 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11297 _diffrn_reflns_av_R_equivalents 0.0681 _diffrn_reflns_av_sigmaI/netI 0.0822 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3752 _reflns_number_gt 2535 _reflns_threshold_expression I>2\s(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^)+(0.0585P)^2^+0.3552P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3752 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1123 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.1472 _refine_ls_wR_factor_gt 0.1333 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.57384(14) 1.10315(15) 0.09818(13) 0.0265(4) Uani 1 1 d . . . O2 O 0.49495(13) 0.97497(14) 0.25222(13) 0.0235(4) Uani 1 1 d . . . N1 N 0.91617(16) 0.89496(17) 0.09581(14) 0.0219(4) Uani 1 1 d . . . C1 C 1.0177(2) 0.9475(2) 0.14436(18) 0.0221(5) Uani 1 1 d . . . C2 C 1.05550(19) 0.9508(2) 0.25987(17) 0.0188(5) Uani 1 1 d . . . C3 C 0.98779(18) 0.89198(18) 0.33010(16) 0.0158(4) Uani 1 1 d . . . C4 C 0.88581(18) 0.81957(18) 0.27926(16) 0.0152(4) Uani 1 1 d . . . C5 C 0.81643(18) 0.74182(19) 0.34005(18) 0.0173(4) Uani 1 1 d . . . C6 C 0.7115(2) 0.6864(2) 0.29033(18) 0.0209(5) Uani 1 1 d . . . C7 C 0.6686(2) 0.7077(2) 0.17792(18) 0.0213(5) Uani 1 1 d . . . C8 C 0.7361(2) 0.7775(2) 0.11605(18) 0.0205(5) Uani 1 1 d . . . C9 C 0.84883(18) 0.83110(19) 0.16363(17) 0.0173(4) Uani 1 1 d . . . C10 C 1.00107(18) 0.91263(19) 0.45308(16) 0.0157(4) Uani 1 1 d . . . C11 C 0.89726(18) 1.00057(19) 0.49003(17) 0.0161(4) Uani 1 1 d . . . C12 C 0.80617(18) 1.05147(19) 0.39661(17) 0.0164(4) Uani 1 1 d . . . C13 C 0.84147(19) 1.13024(19) 0.31777(17) 0.0181(4) Uani 1 1 d . . . C14 C 0.76589(19) 1.1511(2) 0.21744(18) 0.0197(5) Uani 1 1 d . . . C15 C 0.65204(19) 1.0947(2) 0.19629(18) 0.0210(5) Uani 1 1 d . . . C16 C 0.61066(18) 1.02300(19) 0.27892(18) 0.0183(5) Uani 1 1 d . . . C17 C 0.68746(19) 1.00179(19) 0.37744(17) 0.0175(4) Uani 1 1 d . . . C18 C 0.6274(3) 1.1402(3) 0.0031(2) 0.0331(6) Uani 1 1 d . . . C19 C 0.4498(2) 0.8995(2) 0.3335(2) 0.0293(6) Uani 1 1 d . . . H1A H 1.066(2) 0.990(2) 0.0970(18) 0.019(6) Uiso 1 1 d . . . H2A H 1.125(2) 1.000(2) 0.2906(19) 0.027(6) Uiso 1 1 d . . . H5A H 0.843(2) 0.726(2) 0.415(2) 0.028(6) Uiso 1 1 d . . . H6A H 0.666(2) 0.635(2) 0.3314(19) 0.021(6) Uiso 1 1 d . . . H7A H 0.592(2) 0.674(2) 0.144(2) 0.037(7) Uiso 1 1 d . . . H8A H 0.710(2) 0.793(2) 0.044(2) 0.022(6) Uiso 1 1 d . . . H10A H 0.999(2) 0.831(2) 0.4931(19) 0.021(6) Uiso 1 1 d . . . H11A H 0.853(2) 0.958(2) 0.5392(18) 0.017(6) Uiso 1 1 d . . . H13A H 0.920(2) 1.1664(19) 0.3300(17) 0.015(5) Uiso 1 1 d . . . H14A H 0.793(2) 1.201(2) 0.159(2) 0.030(7) Uiso 1 1 d . . . H17A H 0.658(2) 0.947(2) 0.4303(19) 0.026(6) Uiso 1 1 d . . . H18A H 0.565(2) 1.119(2) -0.056(2) 0.031(7) Uiso 1 1 d . . . H18B H 0.704(3) 1.093(3) -0.003(2) 0.045(8) Uiso 1 1 d . . . H18C H 0.650(2) 1.229(2) 0.0051(19) 0.024(6) Uiso 1 1 d . . . H19A H 0.501(2) 0.825(2) 0.351(2) 0.027(6) Uiso 1 1 d . . . H19B H 0.449(2) 0.955(2) 0.408(2) 0.032(7) Uiso 1 1 d . . . H19C H 0.362(3) 0.877(3) 0.306(2) 0.046(8) 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 O1 0.0244(8) 0.0316(9) 0.0201(8) 0.0026(7) -0.0084(6) 0.0003(7) O2 0.0151(7) 0.0254(9) 0.0272(9) -0.0003(7) -0.0061(6) -0.0025(6) N1 0.0233(9) 0.0277(10) 0.0147(9) -0.0025(8) 0.0021(7) -0.0065(8) C1 0.0213(11) 0.0265(12) 0.0194(11) -0.0013(9) 0.0057(9) -0.0048(9) C2 0.0159(10) 0.0225(11) 0.0177(11) -0.0030(9) 0.0008(8) -0.0034(9) C3 0.0151(9) 0.0169(10) 0.0142(10) -0.0006(8) -0.0015(8) 0.0037(8) C4 0.0139(9) 0.0171(10) 0.0142(10) -0.0021(8) 0.0007(8) 0.0032(8) C5 0.0203(10) 0.0180(11) 0.0131(11) -0.0011(8) 0.0012(8) -0.0007(8) C6 0.0212(11) 0.0192(11) 0.0219(12) -0.0009(9) 0.0021(9) -0.0037(9) C7 0.0192(11) 0.0226(12) 0.0209(12) -0.0050(9) -0.0014(9) -0.0043(9) C8 0.0230(11) 0.0272(12) 0.0102(10) -0.0025(9) -0.0017(8) 0.0002(9) C9 0.0178(10) 0.0181(11) 0.0162(11) -0.0039(8) 0.0027(8) -0.0005(8) C10 0.0165(10) 0.0165(11) 0.0130(10) 0.0001(8) -0.0014(8) 0.0014(8) C11 0.0147(10) 0.0199(11) 0.0129(10) 0.0006(8) -0.0006(8) -0.0012(8) C12 0.0151(10) 0.0193(10) 0.0136(10) -0.0025(8) -0.0015(8) 0.0026(8) C13 0.0161(10) 0.0185(11) 0.0186(11) 0.0000(8) -0.0012(8) -0.0007(8) C14 0.0224(11) 0.0192(11) 0.0162(11) 0.0015(9) -0.0018(9) -0.0004(9) C15 0.0212(11) 0.0202(11) 0.0191(11) -0.0003(9) -0.0055(9) 0.0074(9) C16 0.0125(10) 0.0178(11) 0.0230(11) -0.0045(9) -0.0028(8) 0.0014(8) C17 0.0183(10) 0.0161(11) 0.0175(11) -0.0019(9) 0.0006(8) 0.0020(8) C18 0.0355(15) 0.0412(16) 0.0195(13) 0.0025(11) -0.0063(11) -0.0033(13) C19 0.0189(12) 0.0289(13) 0.0389(15) 0.0003(12) 0.0000(10) -0.0055(11) _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 C15 1.373(2) . ? O1 C18 1.433(3) . ? O2 C16 1.370(2) . ? O2 C19 1.430(3) . ? N1 C1 1.316(3) . ? N1 C9 1.376(3) . ? C1 C2 1.412(3) . ? C2 C3 1.372(3) . ? C3 C4 1.436(3) . ? C3 C10 1.505(3) . ? C4 C9 1.418(3) . ? C4 C5 1.418(3) . ? C5 C6 1.363(3) . ? C6 C7 1.405(3) . ? C7 C8 1.364(3) . ? C8 C9 1.415(3) . ? C10 C11 1.549(3) 3_776 ? C10 C11 1.603(3) . ? C11 C12 1.510(3) . ? C11 C10 1.549(3) 3_776 ? C12 C13 1.386(3) . ? C12 C17 1.400(3) . ? C13 C14 1.396(3) . ? C14 C15 1.384(3) . ? C15 C16 1.402(3) . ? C16 C17 1.386(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 C15 O1 C18 116.59(18) . . ? C16 O2 C19 117.16(17) . . ? C1 N1 C9 116.26(18) . . ? N1 C1 C2 124.7(2) . . ? C3 C2 C1 120.3(2) . . ? C2 C3 C4 116.44(18) . . ? C2 C3 C10 124.82(19) . . ? C4 C3 C10 118.10(18) . . ? C9 C4 C5 118.41(18) . . ? C9 C4 C3 118.43(18) . . ? C5 C4 C3 123.09(18) . . ? C6 C5 C4 120.9(2) . . ? C5 C6 C7 120.4(2) . . ? C8 C7 C6 120.0(2) . . ? C7 C8 C9 121.0(2) . . ? N1 C9 C8 118.38(18) . . ? N1 C9 C4 122.86(18) . . ? C8 C9 C4 118.73(19) . . ? C3 C10 C11 119.92(17) . 3_776 ? C3 C10 C11 113.55(16) . . ? C11 C10 C11 90.34(15) 3_776 . ? C12 C11 C10 118.14(18) . 3_776 ? C12 C11 C10 115.29(17) . . ? C10 C11 C10 89.66(15) 3_776 . ? C13 C12 C17 118.02(19) . . ? C13 C12 C11 122.04(18) . . ? C17 C12 C11 118.99(19) . . ? C12 C13 C14 121.32(19) . . ? C15 C14 C13 119.9(2) . . ? O1 C15 C14 124.6(2) . . ? O1 C15 C16 116.00(18) . . ? C14 C15 C16 119.37(19) . . ? O2 C16 C17 124.8(2) . . ? O2 C16 C15 115.28(18) . . ? C17 C16 C15 119.84(19) . . ? C16 C17 C12 121.1(2) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.345 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.061 #===END data_6+HClO4 _database_code_depnum_ccdc_archive 'CCDC 630156' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C38 H36 N2)2+, 2(Cl O4 1-)' _chemical_formula_sum 'C38 H36 Cl2 N2 O12' _chemical_formula_weight 783.59 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 11.4976(5) _cell_length_b 12.2916(6) _cell_length_c 13.5348(6) _cell_angle_alpha 93.589(2) _cell_angle_beta 110.545(2) _cell_angle_gamma 92.542(2) _cell_volume 1783.11(14) _cell_formula_units_Z 2 _cell_measurement_temperature 120.0(2) _cell_measurement_reflns_used 1693 _cell_measurement_theta_min 3.109 _cell_measurement_theta_max 30.128 _exptl_crystal_description plate _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12884 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.1021 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 29.00 _reflns_number_total 8721 _reflns_number_gt 5052 _reflns_threshold_expression I>2\s(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^)+(0.0761P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8721 _refine_ls_number_parameters 631 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1263 _refine_ls_R_factor_gt 0.0614 _refine_ls_wR_factor_ref 0.1547 _refine_ls_wR_factor_gt 0.1350 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _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 0.15146(7) 0.10398(5) 0.21744(5) 0.02264(19) Uani 1 1 d . . . O11 O 0.1888(2) 0.02710(17) 0.29746(17) 0.0312(5) Uani 1 1 d . . . O12 O 0.2590(2) 0.14887(17) 0.19990(18) 0.0326(6) Uani 1 1 d . . . O13 O 0.0923(2) 0.19152(17) 0.25488(18) 0.0344(6) Uani 1 1 d . . . O14 O 0.0643(2) 0.05006(18) 0.12172(17) 0.0407(7) Uani 1 1 d . . . Cl2 Cl 0.81529(8) 0.43340(6) 0.29651(6) 0.0284(2) Uani 1 1 d . . . O21 O 0.8463(2) 0.50542(17) 0.22970(18) 0.0369(6) Uani 1 1 d . . . O22 O 0.7378(3) 0.3435(2) 0.2314(2) 0.0646(10) Uani 1 1 d . . . O23 O 0.7504(2) 0.49104(19) 0.35496(18) 0.0401(6) Uani 1 1 d . . . O24 O 0.9248(4) 0.3956(3) 0.3676(3) 0.0880(12) Uani 1 1 d . . . N1 N 0.2193(3) 0.6725(2) -0.0278(2) 0.0231(6) Uani 1 1 d . . . N2 N -0.2260(3) 0.8339(2) 0.49046(19) 0.0206(6) Uani 1 1 d . . . O1 O -0.56740(19) 0.82493(16) -0.04446(15) 0.0232(5) Uani 1 1 d . . . O2 O -0.49756(19) 0.69996(16) 0.11075(15) 0.0225(5) Uani 1 1 d . . . O3 O 0.57981(18) 0.71854(16) 0.53698(15) 0.0210(5) Uani 1 1 d . . . O4 O 0.50226(19) 0.84387(16) 0.38130(16) 0.0238(5) Uani 1 1 d . . . C1 C 0.1639(3) 0.7636(2) -0.0230(2) 0.0234(7) Uani 1 1 d . . . C2 C 0.0953(3) 0.7779(2) 0.0423(2) 0.0186(6) Uani 1 1 d . . . C3 C 0.0796(3) 0.6947(2) 0.1018(2) 0.0142(6) Uani 1 1 d . . . C4 C 0.1361(3) 0.5949(2) 0.0928(2) 0.0148(6) Uani 1 1 d . . . C5 C 0.1190(3) 0.5016(2) 0.1447(2) 0.0179(6) Uani 1 1 d . . . C6 C 0.1741(3) 0.4079(2) 0.1321(2) 0.0213(7) Uani 1 1 d . . . C7 C 0.2506(3) 0.4021(3) 0.0701(2) 0.0241(7) Uani 1 1 d . . . C8 C 0.2677(3) 0.4898(2) 0.0181(2) 0.0222(7) Uani 1 1 d . . . C9 C 0.2088(3) 0.5851(2) 0.0279(2) 0.0171(6) Uani 1 1 d . . . C10 C 0.0028(3) 0.7046(2) 0.1704(2) 0.0125(5) Uani 1 1 d . . . C11 C -0.0500(3) 0.8148(2) 0.1872(2) 0.0135(6) Uani 1 1 d . . . C12 C -0.1871(3) 0.8221(2) 0.1315(2) 0.0140(6) Uani 1 1 d . . . C13 C -0.2278(3) 0.8904(2) 0.0501(2) 0.0172(6) Uani 1 1 d . . . C14 C -0.3525(3) 0.8922(2) -0.0104(2) 0.0186(6) Uani 1 1 d . . . C15 C -0.4422(3) 0.8283(2) 0.0109(2) 0.0166(6) Uani 1 1 d . . . C16 C -0.4028(3) 0.7597(2) 0.0947(2) 0.0152(6) Uani 1 1 d . . . C17 C -0.2778(3) 0.7562(2) 0.1526(2) 0.0158(6) Uani 1 1 d . . . C18 C -0.6040(3) 0.8790(3) -0.1406(3) 0.0262(7) Uani 1 1 d . . . C19 C -0.4618(3) 0.6359(3) 0.2002(3) 0.0276(8) Uani 1 1 d . . . C20 C -0.1750(3) 0.7407(2) 0.4838(2) 0.0197(6) Uani 1 1 d . . . C21 C -0.0951(3) 0.7303(2) 0.4284(2) 0.0164(6) Uani 1 1 d . . . C22 C -0.0687(2) 0.8163(2) 0.3769(2) 0.0136(6) Uani 1 1 d . . . C23 C -0.1196(3) 0.9186(2) 0.3891(2) 0.0146(6) Uani 1 1 d . . . C24 C -0.0904(3) 1.0148(2) 0.3478(2) 0.0170(6) Uani 1 1 d . . . C25 C -0.1390(3) 1.1106(2) 0.3647(2) 0.0210(6) Uani 1 1 d . . . C26 C -0.2201(3) 1.1158(3) 0.4216(2) 0.0229(7) Uani 1 1 d . . . C27 C -0.2516(3) 1.0245(3) 0.4627(2) 0.0234(7) Uani 1 1 d . . . C28 C -0.1998(3) 0.9264(2) 0.4477(2) 0.0168(6) Uani 1 1 d . . . C29 C 0.0102(3) 0.8079(2) 0.3108(2) 0.0125(5) Uani 1 1 d . . . C30 C 0.0646(3) 0.6976(2) 0.2943(2) 0.0133(6) Uani 1 1 d . . . C31 C 0.2013(3) 0.6951(2) 0.3506(2) 0.0141(6) Uani 1 1 d . . . C32 C 0.2454(3) 0.6270(2) 0.4312(2) 0.0165(6) Uani 1 1 d . . . C33 C 0.3711(3) 0.6330(2) 0.4952(2) 0.0183(6) Uani 1 1 d . . . C34 C 0.4552(3) 0.7062(2) 0.4779(2) 0.0160(6) Uani 1 1 d . . . C35 C 0.4123(3) 0.7742(2) 0.3942(2) 0.0166(6) Uani 1 1 d . . . C36 C 0.2878(3) 0.7690(2) 0.3328(2) 0.0158(6) Uani 1 1 d . . . C37 C 0.6225(3) 0.6531(3) 0.6250(2) 0.0251(7) Uani 1 1 d . . . C38 C 0.4626(3) 0.9070(3) 0.2909(3) 0.0293(8) Uani 1 1 d . . . H1N H 0.266(3) 0.665(3) -0.066(3) 0.033(10) Uiso 1 1 d . . . H2N H -0.279(3) 0.838(3) 0.518(3) 0.028(10) Uiso 1 1 d . . . H1A H 0.175(3) 0.817(2) -0.070(2) 0.028(8) Uiso 1 1 d . . . H2A H 0.057(3) 0.840(3) 0.044(2) 0.028(9) Uiso 1 1 d . . . H5A H 0.066(3) 0.501(2) 0.187(2) 0.018(8) Uiso 1 1 d . . . H6A H 0.154(3) 0.349(3) 0.156(3) 0.032(9) Uiso 1 1 d . . . H7A H 0.286(3) 0.340(3) 0.065(3) 0.037(10) Uiso 1 1 d . . . H8A H 0.323(3) 0.487(2) -0.022(2) 0.024(8) Uiso 1 1 d . . . H10A H -0.061(3) 0.647(2) 0.144(2) 0.014(7) Uiso 1 1 d . . . H11A H -0.008(3) 0.873(3) 0.171(2) 0.029(9) Uiso 1 1 d . . . H13A H -0.167(3) 0.937(2) 0.035(2) 0.025(8) Uiso 1 1 d . . . H14A H -0.371(3) 0.935(3) -0.061(3) 0.034(9) Uiso 1 1 d . . . H17A H -0.249(2) 0.708(2) 0.208(2) 0.008(7) Uiso 1 1 d . . . H18A H -0.583(3) 0.962(2) -0.125(2) 0.020(8) Uiso 1 1 d . . . H18B H -0.567(3) 0.849(2) -0.194(2) 0.020(8) Uiso 1 1 d . . . H18C H -0.688(3) 0.866(3) -0.172(3) 0.035(10) Uiso 1 1 d . . . H19A H -0.540(3) 0.604(3) 0.202(2) 0.028(9) Uiso 1 1 d . . . H19B H -0.409(3) 0.571(3) 0.183(2) 0.031(9) Uiso 1 1 d . . . H19C H -0.420(3) 0.677(3) 0.257(3) 0.024(9) Uiso 1 1 d . . . H20A H -0.196(3) 0.683(3) 0.513(3) 0.038(10) Uiso 1 1 d . . . H21A H -0.059(3) 0.666(3) 0.427(2) 0.024(9) Uiso 1 1 d . . . H24A H -0.039(3) 1.010(2) 0.309(2) 0.012(7) Uiso 1 1 d . . . H25A H -0.116(2) 1.173(2) 0.3439(19) 0.003(6) Uiso 1 1 d . . . H26A H -0.257(3) 1.179(3) 0.430(3) 0.038(10) Uiso 1 1 d . . . H27A H -0.306(3) 1.029(3) 0.502(3) 0.037(10) Uiso 1 1 d . . . H29A H 0.078(3) 0.864(2) 0.341(2) 0.014(7) Uiso 1 1 d . . . H30A H 0.018(3) 0.635(2) 0.311(2) 0.014(7) Uiso 1 1 d . . . H32A H 0.188(3) 0.579(2) 0.447(2) 0.021(8) Uiso 1 1 d . . . H33A H 0.400(3) 0.589(3) 0.548(3) 0.032(9) Uiso 1 1 d . . . H36A H 0.257(3) 0.814(2) 0.283(2) 0.011(7) Uiso 1 1 d . . . H37A H 0.611(3) 0.574(3) 0.601(2) 0.020(8) Uiso 1 1 d . . . H37B H 0.584(3) 0.668(2) 0.677(2) 0.018(8) Uiso 1 1 d . . . H37C H 0.715(3) 0.669(3) 0.659(3) 0.032(9) Uiso 1 1 d . . . H38A H 0.428(3) 0.858(3) 0.230(3) 0.027(9) Uiso 1 1 d . . . H38B H 0.537(3) 0.938(3) 0.288(3) 0.033(9) Uiso 1 1 d . . . H38C H 0.404(3) 0.963(3) 0.306(3) 0.030(9) 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 0.0332(5) 0.0170(4) 0.0190(3) 0.0067(3) 0.0105(3) -0.0030(3) O11 0.0387(14) 0.0314(12) 0.0290(12) 0.0171(10) 0.0157(11) 0.0095(10) O12 0.0394(15) 0.0294(12) 0.0374(13) 0.0010(10) 0.0254(12) -0.0073(10) O13 0.0464(15) 0.0241(12) 0.0432(14) 0.0055(10) 0.0279(12) 0.0082(10) O14 0.0551(17) 0.0305(13) 0.0248(12) 0.0043(10) 0.0013(12) -0.0136(11) Cl2 0.0477(5) 0.0174(4) 0.0212(4) 0.0062(3) 0.0134(4) -0.0033(3) O21 0.0514(16) 0.0287(13) 0.0370(13) 0.0050(10) 0.0253(13) -0.0146(11) O22 0.103(3) 0.0443(16) 0.0560(18) -0.0231(13) 0.0499(18) -0.0461(16) O23 0.0614(18) 0.0378(14) 0.0294(13) 0.0024(10) 0.0266(13) 0.0028(12) O24 0.098(3) 0.106(3) 0.054(2) 0.0276(19) 0.009(2) 0.064(2) N1 0.0296(16) 0.0251(14) 0.0227(13) 0.0060(10) 0.0183(13) 0.0048(11) N2 0.0212(15) 0.0277(14) 0.0173(12) 0.0054(10) 0.0112(12) 0.0046(11) O1 0.0180(11) 0.0317(12) 0.0179(10) 0.0136(8) 0.0019(9) 0.0031(9) O2 0.0166(11) 0.0295(11) 0.0203(10) 0.0104(8) 0.0045(9) -0.0037(9) O3 0.0145(11) 0.0288(11) 0.0178(10) 0.0119(8) 0.0016(9) 0.0017(8) O4 0.0197(12) 0.0285(11) 0.0227(11) 0.0145(9) 0.0053(9) -0.0033(9) C1 0.0322(19) 0.0195(15) 0.0253(16) 0.0107(12) 0.0164(15) 0.0065(13) C2 0.0231(17) 0.0159(15) 0.0181(14) 0.0037(11) 0.0083(13) 0.0037(12) C3 0.0149(15) 0.0147(13) 0.0120(12) 0.0023(10) 0.0034(11) -0.0006(11) C4 0.0171(15) 0.0151(13) 0.0099(12) 0.0018(10) 0.0018(11) -0.0003(11) C5 0.0227(17) 0.0167(14) 0.0127(13) 0.0022(10) 0.0042(13) 0.0010(11) C6 0.0294(18) 0.0131(14) 0.0172(14) 0.0033(11) 0.0023(13) 0.0046(12) C7 0.0304(19) 0.0207(16) 0.0176(15) -0.0006(12) 0.0035(14) 0.0105(13) C8 0.0215(17) 0.0280(16) 0.0175(15) 0.0003(12) 0.0069(14) 0.0081(13) C9 0.0165(15) 0.0188(14) 0.0147(13) 0.0023(10) 0.0035(12) 0.0029(11) C10 0.0138(15) 0.0118(13) 0.0141(13) 0.0025(10) 0.0074(11) -0.0009(10) C11 0.0165(15) 0.0111(13) 0.0157(13) 0.0034(10) 0.0087(12) 0.0028(10) C12 0.0167(15) 0.0130(13) 0.0138(13) 0.0016(10) 0.0069(12) 0.0031(10) C13 0.0229(17) 0.0163(14) 0.0171(14) 0.0063(10) 0.0118(13) 0.0030(11) C14 0.0242(17) 0.0179(14) 0.0168(14) 0.0108(11) 0.0088(13) 0.0068(12) C15 0.0171(15) 0.0189(14) 0.0132(13) 0.0036(10) 0.0039(12) 0.0037(11) C16 0.0181(16) 0.0166(14) 0.0115(13) 0.0023(10) 0.0059(12) -0.0001(11) C17 0.0223(16) 0.0139(13) 0.0110(13) 0.0035(10) 0.0054(12) 0.0007(11) C18 0.026(2) 0.0291(18) 0.0197(16) 0.0118(13) 0.0009(15) 0.0035(14) C19 0.0247(19) 0.036(2) 0.0214(17) 0.0131(14) 0.0063(15) -0.0051(15) C20 0.0229(17) 0.0198(15) 0.0184(14) 0.0047(11) 0.0094(13) 0.0017(12) C21 0.0181(16) 0.0159(14) 0.0158(14) 0.0040(11) 0.0059(12) 0.0051(11) C22 0.0109(14) 0.0158(13) 0.0116(12) 0.0009(10) 0.0008(11) 0.0019(10) C23 0.0155(15) 0.0180(14) 0.0086(12) 0.0015(10) 0.0018(11) 0.0044(11) C24 0.0183(16) 0.0168(14) 0.0151(13) 0.0026(10) 0.0046(13) 0.0014(11) C25 0.0241(17) 0.0166(15) 0.0167(14) 0.0036(11) -0.0005(13) 0.0050(12) C26 0.0236(18) 0.0221(16) 0.0171(15) -0.0013(12) -0.0006(13) 0.0095(13) C27 0.0232(18) 0.0320(17) 0.0151(14) 0.0010(12) 0.0064(14) 0.0093(13) C28 0.0149(15) 0.0223(15) 0.0116(13) 0.0024(10) 0.0023(12) 0.0042(11) C29 0.0151(15) 0.0110(13) 0.0127(12) 0.0014(9) 0.0062(11) 0.0004(10) C30 0.0172(15) 0.0124(13) 0.0117(12) 0.0037(10) 0.0063(11) 0.0019(10) C31 0.0170(15) 0.0114(13) 0.0149(13) 0.0019(10) 0.0066(12) 0.0031(10) C32 0.0215(16) 0.0131(13) 0.0172(14) 0.0053(10) 0.0092(13) 0.0018(11) C33 0.0237(17) 0.0155(14) 0.0159(14) 0.0077(11) 0.0057(13) 0.0047(12) C34 0.0159(15) 0.0179(14) 0.0131(13) 0.0019(10) 0.0037(12) 0.0021(11) C35 0.0195(16) 0.0163(14) 0.0164(13) 0.0032(10) 0.0092(12) 0.0007(11) C36 0.0197(16) 0.0153(14) 0.0137(13) 0.0071(10) 0.0060(12) 0.0056(11) C37 0.0255(19) 0.0279(18) 0.0183(15) 0.0116(13) 0.0017(15) 0.0028(14) C38 0.0228(19) 0.037(2) 0.0267(18) 0.0181(15) 0.0055(15) -0.0054(16) _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 O14 1.430(2) . ? Cl1 O12 1.432(2) . ? Cl1 O11 1.445(2) . ? Cl1 O13 1.455(2) . ? Cl2 O24 1.409(3) . ? Cl2 O21 1.424(2) . ? Cl2 O22 1.425(2) . ? Cl2 O23 1.441(3) . ? N1 C1 1.322(4) . ? N1 C9 1.375(3) . ? N2 C20 1.322(4) . ? N2 C28 1.376(3) . ? O1 C15 1.367(3) . ? O1 C18 1.435(3) . ? O2 C16 1.374(3) . ? O2 C19 1.434(3) . ? O3 C34 1.370(3) . ? O3 C37 1.432(3) . ? O4 C35 1.379(3) . ? O4 C38 1.438(3) . ? C1 C2 1.384(4) . ? C2 C3 1.385(3) . ? C3 C4 1.431(4) . ? C3 C10 1.493(4) . ? C4 C9 1.413(4) . ? C4 C5 1.422(4) . ? C5 C6 1.368(4) . ? C6 C7 1.414(4) . ? C7 C8 1.367(4) . ? C8 C9 1.402(4) . ? C10 C11 1.544(4) . ? C10 C30 1.584(4) . ? C11 C12 1.499(4) . ? C11 C29 1.579(4) . ? C12 C13 1.388(4) . ? C12 C17 1.410(4) . ? C13 C14 1.381(4) . ? C14 C15 1.389(4) . ? C15 C16 1.412(4) . ? C16 C17 1.379(4) . ? C20 C21 1.380(4) . ? C21 C22 1.381(4) . ? C22 C23 1.434(4) . ? C22 C29 1.485(4) . ? C23 C24 1.414(4) . ? C23 C28 1.416(4) . ? C24 C25 1.367(4) . ? C25 C26 1.404(5) . ? C26 C27 1.372(4) . ? C27 C28 1.403(4) . ? C29 C30 1.554(4) . ? C30 C31 1.490(4) . ? C31 C32 1.383(4) . ? C31 C36 1.410(4) . ? C32 C33 1.396(4) . ? C33 C34 1.382(4) . ? C34 C35 1.410(4) . ? C35 C36 1.376(4) . ? 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 O14 Cl1 O12 110.68(14) . . ? O14 Cl1 O11 109.57(13) . . ? O12 Cl1 O11 109.54(14) . . ? O14 Cl1 O13 109.15(16) . . ? O12 Cl1 O13 109.29(13) . . ? O11 Cl1 O13 108.57(13) . . ? O24 Cl2 O21 109.6(2) . . ? O24 Cl2 O22 109.9(2) . . ? O21 Cl2 O22 108.19(14) . . ? O24 Cl2 O23 109.59(18) . . ? O21 Cl2 O23 109.23(14) . . ? O22 Cl2 O23 110.30(17) . . ? C1 N1 C9 122.5(3) . . ? C20 N2 C28 123.2(3) . . ? C15 O1 C18 115.8(2) . . ? C16 O2 C19 116.1(2) . . ? C34 O3 C37 116.5(2) . . ? C35 O4 C38 116.3(2) . . ? N1 C1 C2 121.4(3) . . ? C1 C2 C3 120.3(3) . . ? C2 C3 C4 117.8(3) . . ? C2 C3 C10 122.3(3) . . ? C4 C3 C10 119.9(2) . . ? C9 C4 C5 117.4(3) . . ? C9 C4 C3 120.0(2) . . ? C5 C4 C3 122.5(3) . . ? C6 C5 C4 119.9(3) . . ? C5 C6 C7 121.3(3) . . ? C8 C7 C6 120.3(3) . . ? C7 C8 C9 118.8(3) . . ? N1 C9 C8 120.0(3) . . ? N1 C9 C4 117.9(3) . . ? C8 C9 C4 122.1(3) . . ? C3 C10 C11 120.1(2) . . ? C3 C10 C30 120.3(2) . . ? C11 C10 C30 91.23(19) . . ? C12 C11 C10 116.5(2) . . ? C12 C11 C29 122.5(2) . . ? C10 C11 C29 89.10(19) . . ? C13 C12 C17 117.8(3) . . ? C13 C12 C11 119.2(2) . . ? C17 C12 C11 122.8(2) . . ? C14 C13 C12 121.5(2) . . ? C13 C14 C15 120.9(3) . . ? O1 C15 C14 125.0(2) . . ? O1 C15 C16 116.6(2) . . ? C14 C15 C16 118.5(3) . . ? O2 C16 C17 125.2(2) . . ? O2 C16 C15 114.7(2) . . ? C17 C16 C15 120.1(2) . . ? C16 C17 C12 121.2(2) . . ? N2 C20 C21 120.7(3) . . ? C20 C21 C22 120.7(3) . . ? C21 C22 C23 118.1(3) . . ? C21 C22 C29 123.1(2) . . ? C23 C22 C29 118.8(2) . . ? C24 C23 C28 117.5(3) . . ? C24 C23 C22 123.1(3) . . ? C28 C23 C22 119.4(2) . . ? C25 C24 C23 120.3(3) . . ? C24 C25 C26 121.1(3) . . ? C27 C26 C25 120.6(3) . . ? C26 C27 C28 118.6(3) . . ? N2 C28 C27 120.4(3) . . ? N2 C28 C23 117.7(3) . . ? C27 C28 C23 121.8(3) . . ? C22 C29 C30 120.1(2) . . ? C22 C29 C11 119.7(2) . . ? C30 C29 C11 91.08(19) . . ? C31 C30 C29 114.8(2) . . ? C31 C30 C10 123.3(2) . . ? C29 C30 C10 88.58(19) . . ? C32 C31 C36 118.1(3) . . ? C32 C31 C30 119.6(2) . . ? C36 C31 C30 122.0(2) . . ? C31 C32 C33 121.2(2) . . ? C34 C33 C32 120.5(3) . . ? O3 C34 C33 124.6(2) . . ? O3 C34 C35 116.5(2) . . ? C33 C34 C35 119.0(3) . . ? C36 C35 O4 124.5(2) . . ? C36 C35 C34 120.1(2) . . ? O4 C35 C34 115.4(2) . . ? C35 C36 C31 121.2(2) . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.670 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.081 #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 630157' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C42 H44 N2 O4), 2(Cl O4)1-, (C6 H6)' _chemical_formula_sum 'C48 H50 Cl2 N2 O12' _chemical_formula_weight 917.80 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 'P 1 2(1)/n 1' 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 7.7053(9) _cell_length_b 20.304(2) _cell_length_c 14.3081(15) _cell_angle_alpha 90.00 _cell_angle_beta 99.737(5) _cell_angle_gamma 90.00 _cell_volume 2206.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120.0(2) _cell_measurement_reflns_used 2043 _cell_measurement_theta_min 2.472 _cell_measurement_theta_max 29.734 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART-1K' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11384 _diffrn_reflns_av_R_equivalents 0.1426 _diffrn_reflns_av_sigmaI/netI 0.2346 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5204 _reflns_number_gt 2180 _reflns_threshold_expression I>2\s(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^)+(0.1332P)^2^+7.8505P] 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 5204 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2886 _refine_ls_R_factor_gt 0.1495 _refine_ls_wR_factor_ref 0.3606 _refine_ls_wR_factor_gt 0.3078 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.4293(3) 0.59937(10) -0.20938(14) 0.0272(5) Uani 1 1 d . . . O1' O 0.4644(7) 0.5982(3) -0.1093(4) 0.0292(15) Uani 0.90 1 d P . . O2' O 0.2805(8) 0.5571(3) -0.2444(4) 0.0311(16) Uani 0.90 1 d P . . O3' O 0.5815(10) 0.5750(4) -0.2430(5) 0.049(2) Uani 0.90 1 d P . . O4' O 0.3918(12) 0.6650(3) -0.2433(6) 0.063(3) Uani 0.90 1 d P . . O1 O 0.4859(7) 0.6429(2) -0.8166(4) 0.0222(12) Uani 1 1 d . . . O2 O 0.4671(9) 0.7602(3) -0.7571(4) 0.0378(16) Uani 1 1 d . . . N1 N 0.0048(8) 0.6078(3) -0.7154(4) 0.0217(15) Uani 1 1 d . . . C1 C 0.4857(12) 0.5771(4) -0.8551(5) 0.0265(19) Uani 1 1 d . . . H1A H 0.4697 0.5795 -0.9244 0.040 Uiso 1 1 calc R . . H1B H 0.3893 0.5517 -0.8362 0.040 Uiso 1 1 calc R . . H1C H 0.5982 0.5556 -0.8308 0.040 Uiso 1 1 calc R . . C2 C 0.4340(19) 0.8253(5) -0.7287(7) 0.068(4) Uani 1 1 d . . . H2A H 0.4125 0.8540 -0.7846 0.103 Uiso 1 1 calc R . . H2B H 0.5364 0.8415 -0.6846 0.103 Uiso 1 1 calc R . . H2C H 0.3304 0.8255 -0.6973 0.103 Uiso 1 1 calc R . . C3 C 0.5006(10) 0.7132(4) -0.6868(6) 0.0214(17) Uani 1 1 d . . . C4 C 0.5279(11) 0.7247(4) -0.5905(6) 0.0275(19) Uani 1 1 d . . . H4A H 0.5298 0.7687 -0.5678 0.033 Uiso 1 1 calc R . . C5 C 0.5531(11) 0.6723(4) -0.5251(5) 0.0222(18) Uani 1 1 d . . . H5A H 0.5703 0.6810 -0.4590 0.027 Uiso 1 1 calc R . . C6 C 0.5529(10) 0.6081(3) -0.5575(5) 0.0193(17) Uani 1 1 d . . . C7 C 0.5320(10) 0.5969(4) -0.6557(5) 0.0224(17) Uani 1 1 d . . . H7A H 0.5348 0.5529 -0.6783 0.027 Uiso 1 1 calc R . . C8 C 0.5074(9) 0.6482(4) -0.7205(6) 0.0205(17) Uani 1 1 d . . . C9 C 0.5468(10) 0.5524(4) -0.4883(5) 0.0212(17) Uani 1 1 d . . . C10 C 0.3618(11) 0.5142(4) -0.4931(5) 0.0225(18) Uani 1 1 d . . . C11 C 0.2186(11) 0.5411(4) -0.5677(5) 0.0238(18) Uani 1 1 d . . . C12 C 0.1457(10) 0.6049(4) -0.5508(5) 0.0182(16) Uani 1 1 d . . . C13 C 0.1770(11) 0.6354(4) -0.4623(5) 0.0262(19) Uani 1 1 d . . . H13A H 0.2438 0.6129 -0.4100 0.031 Uiso 1 1 calc R . . C14 C 0.1117(11) 0.6986(4) -0.4488(6) 0.0268(19) Uani 1 1 d . . . H14A H 0.1308 0.7185 -0.3878 0.032 Uiso 1 1 calc R . . C15 C 0.0177(12) 0.7317(4) -0.5274(6) 0.034(2) Uani 1 1 d . . . H15A H -0.0225 0.7751 -0.5189 0.041 Uiso 1 1 calc R . . C16 C -0.0182(11) 0.7043(4) -0.6148(6) 0.028(2) Uani 1 1 d . . . H16A H -0.0828 0.7281 -0.6664 0.034 Uiso 1 1 calc R . . C17 C 0.0431(10) 0.6384(4) -0.6285(5) 0.0195(17) Uani 1 1 d . . . C18 C 0.0560(10) 0.5455(4) -0.7269(6) 0.0247(18) Uani 1 1 d . . . H18A H 0.0190 0.5238 -0.7857 0.030 Uiso 1 1 calc R . . C19 C 0.1614(10) 0.5126(4) -0.6543(5) 0.0186(16) Uani 1 1 d . . . H19A H 0.1957 0.4686 -0.6646 0.022 Uiso 1 1 calc R . . C20 C -0.0846(11) 0.6437(4) -0.8012(6) 0.0259(18) Uani 1 1 d . . . H20A H -0.1841 0.6695 -0.7847 0.031 Uiso 1 1 calc R . . H20B H -0.1329 0.6114 -0.8506 0.031 Uiso 1 1 calc R . . C21 C 0.0416(12) 0.6898(4) -0.8403(6) 0.031(2) Uani 1 1 d . . . H21A H -0.0210 0.7123 -0.8966 0.047 Uiso 1 1 calc R . . H21B H 0.1394 0.6642 -0.8575 0.047 Uiso 1 1 calc R . . H21C H 0.0876 0.7224 -0.7919 0.047 Uiso 1 1 calc R . . C1S C 0.9126(14) 0.4482(5) 0.0357(7) 0.043(2) Uani 1 1 d . . . C2S C 0.8211(12) 0.5049(5) 0.0058(6) 0.035(2) Uani 1 1 d . . . C3S C 0.9097(13) 0.5570(5) -0.0299(6) 0.039(2) Uani 1 1 d . . . H9A H 0.583(10) 0.561(4) -0.418(5) 0.022 Uiso 1 1 d . . . H10A H 0.329(11) 0.519(4) -0.433(6) 0.030 Uiso 1 1 d . . . H1SA H 0.843(16) 0.413(6) 0.067(9) 0.087 Uiso 1 1 d . . . H2SA H 0.705(12) 0.497(4) 0.019(5) 0.028 Uiso 1 1 d . . . H3SA H 0.835(13) 0.588(5) -0.056(7) 0.046 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 0.0337(12) 0.0235(10) 0.0228(10) -0.0018(9) 0.0002(8) 0.0001(9) O1' 0.014(3) 0.043(4) 0.031(3) -0.008(3) 0.005(3) -0.010(3) O2' 0.038(4) 0.015(3) 0.033(4) -0.003(3) -0.016(3) 0.001(3) O3' 0.042(5) 0.065(5) 0.049(4) -0.013(4) 0.032(4) -0.019(4) O4' 0.095(7) 0.009(3) 0.065(5) 0.007(4) -0.046(5) -0.007(4) O1 0.025(3) 0.019(3) 0.023(3) 0.004(2) 0.005(2) -0.001(2) O2 0.060(5) 0.020(3) 0.038(4) 0.009(3) 0.024(3) 0.008(3) N1 0.018(4) 0.023(4) 0.024(3) 0.001(3) 0.001(3) 0.001(3) C1 0.037(5) 0.025(4) 0.017(4) -0.007(3) 0.004(3) -0.004(4) C2 0.150(13) 0.020(5) 0.048(7) 0.015(5) 0.052(8) 0.030(6) C3 0.016(4) 0.018(4) 0.035(5) 0.008(3) 0.018(3) -0.001(3) C4 0.025(5) 0.015(4) 0.045(5) -0.008(4) 0.016(4) -0.001(3) C5 0.033(5) 0.020(4) 0.014(4) -0.006(3) 0.008(3) 0.006(4) C6 0.019(4) 0.013(4) 0.025(4) -0.002(3) 0.003(3) 0.012(3) C7 0.027(5) 0.013(4) 0.025(4) -0.005(3) -0.001(3) -0.006(3) C8 0.006(4) 0.021(4) 0.035(4) -0.006(3) 0.007(3) -0.006(3) C9 0.031(5) 0.023(4) 0.008(4) 0.002(3) -0.001(3) 0.008(3) C10 0.033(5) 0.014(4) 0.019(4) 0.000(3) -0.001(3) 0.012(3) C11 0.030(5) 0.019(4) 0.024(4) 0.002(3) 0.009(3) 0.008(4) C12 0.017(4) 0.019(4) 0.019(4) 0.009(3) 0.002(3) 0.004(3) C13 0.026(5) 0.030(5) 0.024(4) 0.007(4) 0.008(4) 0.014(4) C14 0.030(5) 0.024(4) 0.027(4) 0.000(4) 0.006(4) 0.014(4) C15 0.028(5) 0.033(5) 0.044(5) 0.007(4) 0.012(4) 0.016(4) C16 0.027(5) 0.035(5) 0.022(4) 0.015(4) 0.004(3) 0.018(4) C17 0.013(4) 0.027(4) 0.019(4) 0.005(3) 0.004(3) -0.002(3) C18 0.022(5) 0.019(4) 0.032(4) -0.009(4) 0.000(3) -0.005(3) C19 0.011(4) 0.017(4) 0.028(4) -0.002(3) 0.004(3) 0.002(3) C20 0.019(5) 0.030(5) 0.026(4) 0.001(4) -0.005(3) 0.001(4) C21 0.035(5) 0.036(5) 0.023(4) 0.008(4) 0.005(4) 0.006(4) C1S 0.040(6) 0.049(6) 0.036(5) 0.002(5) -0.002(4) -0.009(5) C2S 0.021(5) 0.054(6) 0.030(5) -0.010(4) 0.002(4) -0.015(5) C3S 0.032(6) 0.055(7) 0.025(5) -0.009(5) -0.014(4) 0.008(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 Cl1 O1' 1.412(6) . ? Cl1 O3' 1.430(7) . ? Cl1 O4' 1.431(7) . ? Cl1 O2' 1.451(6) . ? O1 C8 1.361(9) . ? O1 C1 1.444(9) . ? O2 C3 1.378(9) . ? O2 C2 1.419(10) . ? N1 C18 1.345(10) . ? N1 C17 1.377(9) . ? N1 C20 1.491(9) . ? C3 C4 1.378(11) . ? C3 C8 1.409(11) . ? C4 C5 1.408(11) . ? C5 C6 1.384(10) . ? C6 C7 1.406(10) . ? C6 C9 1.508(10) . ? C7 C8 1.387(11) . ? C9 C10 1.568(10) 3_664 ? C9 C10 1.615(12) . ? C10 C11 1.503(10) . ? C10 C9 1.568(10) 3_664 ? C11 C19 1.370(10) . ? C11 C12 1.450(10) . ? C12 C13 1.394(10) . ? C12 C17 1.423(10) . ? C13 C14 1.404(11) . ? C14 C15 1.401(11) . ? C15 C16 1.355(12) . ? C16 C17 1.443(11) . ? C18 C19 1.379(10) . ? C20 C21 1.522(12) . ? C1S C2S 1.380(14) . ? C1S C3S 1.389(14) 3_765 ? C2S C3S 1.401(14) . ? C3S C1S 1.389(14) 3_765 ? 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' Cl1 O3' 107.9(4) . . ? O1' Cl1 O4' 110.7(5) . . ? O3' Cl1 O4' 109.8(5) . . ? O1' Cl1 O2' 110.2(4) . . ? O3' Cl1 O2' 108.9(4) . . ? O4' Cl1 O2' 109.3(4) . . ? C8 O1 C1 116.8(6) . . ? C3 O2 C2 117.2(7) . . ? C18 N1 C17 120.8(6) . . ? C18 N1 C20 117.6(6) . . ? C17 N1 C20 121.5(6) . . ? C4 C3 O2 126.2(7) . . ? C4 C3 C8 119.4(7) . . ? O2 C3 C8 114.3(7) . . ? C3 C4 C5 121.2(7) . . ? C6 C5 C4 119.8(7) . . ? C5 C6 C7 118.7(7) . . ? C5 C6 C9 119.0(7) . . ? C7 C6 C9 121.6(7) . . ? C8 C7 C6 121.8(7) . . ? O1 C8 C7 126.5(7) . . ? O1 C8 C3 114.5(7) . . ? C7 C8 C3 119.0(7) . . ? C6 C9 C10 118.0(6) . 3_664 ? C6 C9 C10 117.2(6) . . ? C10 C9 C10 89.8(6) 3_664 . ? C11 C10 C9 119.3(6) . 3_664 ? C11 C10 C9 113.1(6) . . ? C9 C10 C9 90.2(6) 3_664 . ? C19 C11 C12 117.0(7) . . ? C19 C11 C10 125.0(7) . . ? C12 C11 C10 117.7(6) . . ? C13 C12 C17 119.1(7) . . ? C13 C12 C11 122.4(6) . . ? C17 C12 C11 118.5(7) . . ? C12 C13 C14 121.3(7) . . ? C15 C14 C13 118.4(8) . . ? C16 C15 C14 122.8(8) . . ? C15 C16 C17 119.0(7) . . ? N1 C17 C12 119.7(7) . . ? N1 C17 C16 121.0(7) . . ? C12 C17 C16 119.3(7) . . ? N1 C18 C19 120.8(7) . . ? C11 C19 C18 122.3(7) . . ? N1 C20 C21 111.6(6) . . ? C2S C1S C3S 120.2(10) . 3_765 ? C1S C2S C3S 119.2(9) . . ? C1S C3S C2S 120.6(9) 3_765 . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.932 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.138 #===END data_7a _database_code_depnum_ccdc_archive 'CCDC 630158' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C42 H44 N2 O4)2+, 2(Cl O4 1-), 3(C6 H6)' _chemical_formula_sum 'C60 H62 Cl2 N2 O12' _chemical_formula_weight 1074.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 11.0230(4) _cell_length_b 11.2484(4) _cell_length_c 12.5132(5) _cell_angle_alpha 82.944(2) _cell_angle_beta 76.649(2) _cell_angle_gamma 61.394(2) _cell_volume 1325.19(9) _cell_formula_units_Z 1 _cell_measurement_temperature 120.0(2) _cell_measurement_reflns_used 3042 _cell_measurement_theta_min 2.448 _cell_measurement_theta_max 29.285 _exptl_crystal_description block _exptl_crystal_colour orangey _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 566 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART-1K' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9388 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0724 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 29.00 _reflns_number_total 6577 _reflns_number_gt 4164 _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^)+(0.0651P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6577 _refine_ls_number_parameters 467 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1156 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _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 0.54221(5) 0.34194(5) 0.26896(4) 0.02837(14) Uani 1 1 d . . . O11 O 0.62677(16) 0.19955(14) 0.28876(14) 0.0379(4) Uani 1 1 d . . . O12 O 0.63004(17) 0.40215(16) 0.21613(14) 0.0409(4) Uani 1 1 d . . . O13 O 0.46402(18) 0.40607(16) 0.37317(14) 0.0458(4) Uani 1 1 d . . . O14 O 0.44467(19) 0.36047(17) 0.20221(16) 0.0494(5) Uani 1 1 d . . . O1 O -0.17345(14) 0.32110(14) 0.51285(12) 0.0299(3) Uani 1 1 d . . . O2 O -0.04064(14) 0.08983(13) 0.60995(12) 0.0275(3) Uani 1 1 d . . . N1 N 0.34776(16) -0.20991(15) 0.24676(13) 0.0215(4) Uani 1 1 d . . . C1 C 0.3983(2) -0.2684(2) 0.33654(17) 0.0230(4) Uani 1 1 d . . . C2 C 0.4531(2) -0.2128(2) 0.39373(17) 0.0220(4) Uani 1 1 d . . . C3 C 0.45993(19) -0.09559(18) 0.35811(16) 0.0198(4) Uani 1 1 d . . . C4 C 0.40829(19) -0.03240(19) 0.25992(16) 0.0210(4) Uani 1 1 d . . . C5 C 0.4149(2) 0.0866(2) 0.21331(18) 0.0263(5) Uani 1 1 d . . . C6 C 0.3645(2) 0.1444(2) 0.11965(19) 0.0325(5) Uani 1 1 d . . . C7 C 0.3024(3) 0.0887(2) 0.0695(2) 0.0347(5) Uani 1 1 d . . . C8 C 0.2931(2) -0.0254(2) 0.11135(18) 0.0298(5) Uani 1 1 d . . . C9 C 0.3493(2) -0.08937(19) 0.20527(16) 0.0228(4) Uani 1 1 d . . . C10 C 0.52091(19) -0.03301(18) 0.41540(16) 0.0193(4) Uani 1 1 d . . . C11 C 0.4172(2) 0.10284(19) 0.48100(16) 0.0202(4) Uani 1 1 d . . . C12 C 0.2602(2) 0.16153(19) 0.49132(16) 0.0210(4) Uani 1 1 d . . . C13 C 0.1861(2) 0.2855(2) 0.44163(17) 0.0236(4) Uani 1 1 d . . . C14 C 0.0419(2) 0.3414(2) 0.44793(18) 0.0268(5) Uani 1 1 d . . . C15 C -0.0319(2) 0.27493(19) 0.50411(17) 0.0248(4) Uani 1 1 d . . . C16 C 0.0410(2) 0.14915(19) 0.55573(16) 0.0229(4) Uani 1 1 d . . . C17 C 0.1856(2) 0.0932(2) 0.54833(17) 0.0219(4) Uani 1 1 d . . . C18 C -0.2391(3) 0.4254(3) 0.4352(2) 0.0351(5) Uani 1 1 d . . . C19 C 0.0333(3) -0.0457(2) 0.6499(2) 0.0299(5) Uani 1 1 d . . . C20 C 0.2903(2) -0.2758(2) 0.19010(19) 0.0304(5) Uani 1 1 d . . . C21 C 0.3872(3) -0.3428(3) 0.0849(2) 0.0362(6) Uani 1 1 d . . . C1S C 0.8266(3) 0.6945(3) 0.2240(3) 0.0557(8) Uani 1 1 d . . . C2S C 0.7745(3) 0.6335(3) 0.1721(2) 0.0541(7) Uani 1 1 d . . . C3S C 0.8622(4) 0.5061(3) 0.1295(3) 0.0588(8) Uani 1 1 d . . . C4S C 1.0020(4) 0.4416(3) 0.1388(3) 0.0639(9) Uani 1 1 d . . . C5S C 1.0550(4) 0.5041(3) 0.1906(2) 0.0593(8) Uani 1 1 d . . . C6S C 0.9658(3) 0.6310(3) 0.2334(2) 0.0526(7) Uani 1 1 d . . . C7S C -0.0932(3) 0.9838(3) 0.0886(2) 0.0408(6) Uani 1 1 d . . . C8S C 0.0067(3) 0.8737(3) 0.0249(2) 0.0402(6) Uani 1 1 d . . . C9S C 0.0994(3) 0.8901(3) -0.0635(2) 0.0402(6) Uani 1 1 d . . . H1 H 0.396(2) -0.353(2) 0.3590(18) 0.030(6) Uiso 1 1 d . . . H2 H 0.480(2) -0.2546(19) 0.4534(17) 0.017(5) Uiso 1 1 d . . . H5 H 0.454(2) 0.123(2) 0.2464(17) 0.022(5) Uiso 1 1 d . . . H6 H 0.371(3) 0.220(2) 0.092(2) 0.045(7) Uiso 1 1 d . . . H7 H 0.265(3) 0.132(2) 0.004(2) 0.042(7) Uiso 1 1 d . . . H8 H 0.253(2) -0.061(2) 0.0755(18) 0.029(6) Uiso 1 1 d . . . H10 H 0.588(2) -0.0168(19) 0.3597(17) 0.020(5) Uiso 1 1 d . . . H11 H 0.443(2) 0.1690(19) 0.4510(16) 0.017(5) Uiso 1 1 d . . . H13 H 0.234(2) 0.330(2) 0.4033(18) 0.028(6) Uiso 1 1 d . . . H14 H -0.004(2) 0.425(2) 0.4167(16) 0.018(5) Uiso 1 1 d . . . H17 H 0.2287(19) 0.0104(19) 0.5805(15) 0.013(5) Uiso 1 1 d . . . H18A H -0.331(2) 0.432(2) 0.4453(17) 0.029(6) Uiso 1 1 d . . . H18B H -0.241(3) 0.510(3) 0.451(2) 0.050(8) Uiso 1 1 d . . . H18C H -0.189(2) 0.398(2) 0.358(2) 0.035(6) Uiso 1 1 d . . . H19A H 0.104(2) -0.107(2) 0.5928(19) 0.028(6) Uiso 1 1 d . . . H19B H -0.042(2) -0.075(2) 0.6798(17) 0.027(6) Uiso 1 1 d . . . H19C H 0.080(2) -0.0519(19) 0.7074(17) 0.020(5) Uiso 1 1 d . . . H20A H 0.273(2) -0.339(2) 0.2473(19) 0.034(6) Uiso 1 1 d . . . H20B H 0.194(3) -0.205(2) 0.1761(19) 0.039(6) Uiso 1 1 d . . . H21A H 0.348(2) -0.388(2) 0.0626(19) 0.033(6) Uiso 1 1 d . . . H21B H 0.399(3) -0.282(3) 0.031(2) 0.049(8) Uiso 1 1 d . . . H21C H 0.481(3) -0.406(2) 0.0956(19) 0.035(6) Uiso 1 1 d . . . H1S H 0.773(4) 0.784(3) 0.254(3) 0.086(11) Uiso 1 1 d . . . H2S H 0.676(3) 0.677(3) 0.163(2) 0.064(9) Uiso 1 1 d . . . H3S H 0.819(3) 0.464(3) 0.084(3) 0.087(11) Uiso 1 1 d . . . H4S H 1.064(4) 0.342(4) 0.106(3) 0.114(13) Uiso 1 1 d . . . H5S H 1.156(4) 0.462(3) 0.193(3) 0.078(10) Uiso 1 1 d . . . H6S H 1.003(3) 0.674(3) 0.271(3) 0.075(10) Uiso 1 1 d . . . H7S H -0.163(3) 0.971(2) 0.151(2) 0.050(7) Uiso 1 1 d . . . H8S H 0.015(3) 0.782(3) 0.040(2) 0.050(8) Uiso 1 1 d . . . H9S H 0.160(3) 0.813(3) -0.105(2) 0.054(8) 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 0.0273(3) 0.0260(3) 0.0347(3) 0.0027(2) -0.0086(2) -0.0144(2) O11 0.0304(8) 0.0256(8) 0.0516(11) 0.0044(7) -0.0080(7) -0.0094(7) O12 0.0411(9) 0.0443(10) 0.0502(11) 0.0102(8) -0.0130(8) -0.0308(8) O13 0.0511(11) 0.0354(9) 0.0429(11) -0.0054(8) 0.0018(8) -0.0176(8) O14 0.0600(12) 0.0461(10) 0.0650(12) 0.0184(9) -0.0403(10) -0.0351(9) O1 0.0174(7) 0.0300(8) 0.0381(9) 0.0036(7) -0.0104(6) -0.0065(6) O2 0.0213(7) 0.0278(8) 0.0337(9) 0.0028(6) -0.0068(6) -0.0120(6) N1 0.0199(8) 0.0227(8) 0.0246(9) -0.0027(7) -0.0079(7) -0.0100(7) C1 0.0219(10) 0.0236(10) 0.0252(11) -0.0006(8) -0.0055(8) -0.0115(8) C2 0.0210(10) 0.0248(10) 0.0206(11) 0.0008(8) -0.0078(8) -0.0096(8) C3 0.0145(9) 0.0220(9) 0.0221(10) -0.0036(8) -0.0046(7) -0.0068(8) C4 0.0175(9) 0.0225(10) 0.0220(10) -0.0035(8) -0.0053(7) -0.0071(8) C5 0.0283(11) 0.0247(10) 0.0307(12) -0.0001(9) -0.0123(9) -0.0133(9) C6 0.0410(13) 0.0251(11) 0.0349(13) 0.0046(10) -0.0144(10) -0.0163(10) C7 0.0450(14) 0.0309(12) 0.0314(13) 0.0052(10) -0.0219(11) -0.0152(11) C8 0.0346(12) 0.0266(11) 0.0321(12) -0.0005(9) -0.0180(10) -0.0123(10) C9 0.0202(9) 0.0228(10) 0.0260(11) -0.0030(8) -0.0071(8) -0.0088(8) C10 0.0162(9) 0.0200(9) 0.0228(10) -0.0001(8) -0.0072(8) -0.0077(8) C11 0.0206(9) 0.0201(10) 0.0236(11) -0.0001(8) -0.0079(8) -0.0108(8) C12 0.0201(9) 0.0216(9) 0.0229(10) -0.0041(8) -0.0082(8) -0.0083(8) C13 0.0237(10) 0.0224(10) 0.0264(11) 0.0022(8) -0.0082(8) -0.0112(9) C14 0.0252(10) 0.0202(10) 0.0341(12) 0.0040(9) -0.0125(9) -0.0080(9) C15 0.0189(10) 0.0247(10) 0.0273(11) -0.0052(8) -0.0067(8) -0.0054(8) C16 0.0227(10) 0.0258(10) 0.0233(11) -0.0030(8) -0.0056(8) -0.0127(9) C17 0.0198(10) 0.0196(10) 0.0253(11) -0.0002(8) -0.0094(8) -0.0063(8) C18 0.0243(12) 0.0378(14) 0.0369(15) 0.0024(11) -0.0131(10) -0.0071(10) C19 0.0329(12) 0.0324(12) 0.0304(13) 0.0047(10) -0.0101(10) -0.0194(10) C20 0.0345(12) 0.0313(12) 0.0342(13) -0.0026(10) -0.0148(10) -0.0185(11) C21 0.0454(15) 0.0297(13) 0.0339(14) -0.0043(11) -0.0150(11) -0.0139(12) C1S 0.0501(17) 0.0479(17) 0.0601(19) -0.0140(14) 0.0124(14) -0.0229(14) C2S 0.0429(16) 0.0646(19) 0.0526(18) -0.0024(15) 0.0051(13) -0.0293(15) C3S 0.065(2) 0.071(2) 0.0499(18) -0.0125(15) 0.0031(14) -0.0424(18) C4S 0.064(2) 0.0433(17) 0.065(2) -0.0056(15) -0.0008(16) -0.0138(16) C5S 0.0498(18) 0.066(2) 0.0478(18) 0.0090(15) -0.0106(14) -0.0172(16) C6S 0.064(2) 0.0612(19) 0.0380(16) -0.0056(14) -0.0032(13) -0.0356(17) C7S 0.0372(14) 0.0564(16) 0.0302(14) -0.0006(12) -0.0132(11) -0.0200(13) C8S 0.0421(14) 0.0472(15) 0.0348(14) 0.0002(12) -0.0195(11) -0.0184(12) C9S 0.0375(13) 0.0481(15) 0.0312(14) -0.0048(12) -0.0148(11) -0.0126(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 Cl1 O14 1.4334(17) . ? Cl1 O12 1.4337(15) . ? Cl1 O11 1.4405(15) . ? Cl1 O13 1.4424(17) . ? O1 C15 1.370(2) . ? O1 C18 1.441(3) . ? O2 C16 1.377(2) . ? O2 C19 1.431(3) . ? N1 C1 1.327(2) . ? N1 C9 1.397(2) . ? N1 C20 1.496(2) . ? C1 C2 1.393(3) . ? C2 C3 1.371(3) . ? C3 C4 1.435(3) . ? C3 C10 1.504(3) . ? C4 C9 1.419(3) . ? C4 C5 1.421(3) . ? C5 C6 1.369(3) . ? C6 C7 1.401(3) . ? C7 C8 1.367(3) . ? C8 C9 1.408(3) . ? C10 C11 1.552(3) 2_656 ? C10 C11 1.587(3) . ? C11 C12 1.507(3) . ? C11 C10 1.552(3) 2_656 ? C12 C13 1.389(3) . ? C12 C17 1.405(3) . ? C13 C14 1.387(3) . ? C14 C15 1.380(3) . ? C15 C16 1.411(3) . ? C16 C17 1.390(3) . ? C20 C21 1.505(3) . ? C1S C2S 1.371(4) . ? C1S C6S 1.376(4) . ? C2S C3S 1.377(4) . ? C3S C4S 1.381(4) . ? C4S C5S 1.391(5) . ? C5S C6S 1.376(4) . ? C7S C8S 1.383(3) . ? C7S C9S 1.387(4) 2_575 ? C8S C9S 1.382(4) . ? C9S C7S 1.387(4) 2_575 ? 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 O14 Cl1 O12 110.18(10) . . ? O14 Cl1 O11 109.70(10) . . ? O12 Cl1 O11 110.48(9) . . ? O14 Cl1 O13 108.84(11) . . ? O12 Cl1 O13 109.20(10) . . ? O11 Cl1 O13 108.41(10) . . ? C15 O1 C18 115.86(17) . . ? C16 O2 C19 116.35(16) . . ? C1 N1 C9 120.59(16) . . ? C1 N1 C20 118.89(17) . . ? C9 N1 C20 120.51(16) . . ? N1 C1 C2 122.08(19) . . ? C3 C2 C1 121.17(19) . . ? C2 C3 C4 117.47(17) . . ? C2 C3 C10 123.27(17) . . ? C4 C3 C10 119.25(16) . . ? C9 C4 C5 117.66(18) . . ? C9 C4 C3 120.04(17) . . ? C5 C4 C3 122.29(17) . . ? C6 C5 C4 120.8(2) . . ? C5 C6 C7 120.3(2) . . ? C8 C7 C6 121.0(2) . . ? C7 C8 C9 119.5(2) . . ? N1 C9 C8 120.78(18) . . ? N1 C9 C4 118.61(17) . . ? C8 C9 C4 120.60(18) . . ? C3 C10 C11 120.07(16) . 2_656 ? C3 C10 C11 118.70(15) . . ? C11 C10 C11 90.83(14) 2_656 . ? C12 C11 C10 117.24(16) . 2_656 ? C12 C11 C10 119.96(15) . . ? C10 C11 C10 89.17(14) 2_656 . ? C13 C12 C17 118.37(18) . . ? C13 C12 C11 119.68(18) . . ? C17 C12 C11 121.93(17) . . ? C14 C13 C12 121.22(19) . . ? C15 C14 C13 120.64(19) . . ? O1 C15 C14 124.67(18) . . ? O1 C15 C16 116.13(18) . . ? C14 C15 C16 119.19(18) . . ? O2 C16 C17 124.77(18) . . ? O2 C16 C15 115.38(17) . . ? C17 C16 C15 119.85(18) . . ? C16 C17 C12 120.72(18) . . ? N1 C20 C21 112.66(19) . . ? C2S C1S C6S 121.1(3) . . ? C1S C2S C3S 119.7(3) . . ? C2S C3S C4S 119.6(3) . . ? C3S C4S C5S 120.6(3) . . ? C6S C5S C4S 119.1(3) . . ? C1S C6S C5S 119.9(3) . . ? C8S C7S C9S 119.8(2) . 2_575 ? C9S C8S C7S 119.8(3) . . ? C8S C9S C7S 120.4(2) . 2_575 ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.343 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.055