# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 loop_ _publ_author_name 'Jon Antilla ' 'Yuxue Liang.' 'Jason A. Perman ' 'Emily B. Rowland ' 'Gerald B. Rowland ' _publ_contact_author ;Prof. Jon Antilla Department of Chemistry University of South Florida 4202 E Fowler AveBSF 305 CHE205A Tampa FL 33620 UNITED STATES OF AMERICA ; _publ_contact_author_email JANTILLA@CAS.USF.EDU data_clam1 _database_code_depnum_ccdc_archive 'CCDC 648156' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H19 Cl N2 O4' _chemical_formula_weight 386.82 _chemical_absolute_configuration R 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.565(10) _cell_length_b 12.021(8) _cell_length_c 9.812(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.81(2) _cell_angle_gamma 90.00 _cell_volume 1953(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1392 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 24.96 _exptl_crystal_description parallelepip _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.874 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2370 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0679 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2279 _reflns_number_gt 2028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1462P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(15) _refine_ls_number_reflns 2279 _refine_ls_number_parameters 250 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.1930 _refine_ls_wR_factor_gt 0.1869 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 4.142 _refine_ls_shift/su_mean 0.018 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 1.06417(11) 0.24711(15) 0.18602(19) 0.0547(6) Uani 1 1 d . . . O1 O 0.7036(2) -0.0155(3) 0.3351(4) 0.0338(10) Uani 1 1 d . . . O2 O 0.6622(2) 0.3290(3) 0.5215(4) 0.0292(9) Uani 1 1 d . . . O3 O 0.7400(2) 0.1115(3) 0.8036(3) 0.0347(10) Uani 1 1 d . . . O4 O 0.7809(2) -0.0690(3) 0.7814(3) 0.0332(10) Uani 1 1 d . . . N1 N 0.6999(3) 0.1534(3) 0.4505(4) 0.0267(11) Uani 1 1 d . . . N2 N 0.7853(3) 0.0433(4) 0.6030(4) 0.0289(12) Uani 1 1 d . . . H2 H 0.8024 -0.0160 0.5601 0.035 Uiso 1 1 calc R . . C1 C 0.7783(3) 0.1457(4) 0.5315(5) 0.0269(14) Uani 1 1 d . . . H1 H 0.778(3) 0.206(5) 0.602(6) 0.032 Uiso 1 1 calc . . . C2 C 0.8490(3) 0.1690(4) 0.4408(5) 0.0264(14) Uani 1 1 d . . . C3 C 0.8870(5) 0.0865(5) 0.3672(7) 0.0466(18) Uani 1 1 d . . . H3 H 0.8681 0.0119 0.3705 0.056 Uiso 1 1 calc R . . C4 C 0.9521(5) 0.1127(6) 0.2895(7) 0.0465(17) Uani 1 1 d . . . H4 H 0.9781 0.0557 0.2403 0.056 Uiso 1 1 calc R . . C5 C 0.9792(4) 0.2175(5) 0.2822(6) 0.0387(17) Uani 1 1 d . . . C6 C 0.9420(5) 0.3027(6) 0.3502(8) 0.056(2) Uani 1 1 d . . . H6 H 0.9606 0.3772 0.3437 0.068 Uiso 1 1 calc R . . C7 C 0.8760(4) 0.2760(6) 0.4291(8) 0.0476(18) Uani 1 1 d . . . H7 H 0.8492 0.3337 0.4759 0.057 Uiso 1 1 calc R . . C8 C 0.6699(4) 0.0707(4) 0.3607(5) 0.0265(13) Uani 1 1 d . . . C9 C 0.5915(3) 0.1162(5) 0.3061(5) 0.0272(12) Uani 1 1 d . . . C10 C 0.5354(4) 0.0685(5) 0.2106(5) 0.0369(15) Uani 1 1 d . . . H10 H 0.5442 -0.0022 0.1704 0.044 Uiso 1 1 calc R . . C11 C 0.4669(4) 0.1311(6) 0.1794(6) 0.0415(16) Uani 1 1 d . . . H11 H 0.4274 0.1016 0.1171 0.050 Uiso 1 1 calc R . . C12 C 0.4542(4) 0.2344(6) 0.2353(6) 0.0443(17) Uani 1 1 d . . . H12 H 0.4060 0.2736 0.2114 0.053 Uiso 1 1 calc R . . C13 C 0.5106(4) 0.2832(5) 0.3271(6) 0.0377(16) Uani 1 1 d . . . H13 H 0.5026 0.3551 0.3646 0.045 Uiso 1 1 calc R . . C14 C 0.5789(4) 0.2200(4) 0.3596(5) 0.0316(14) Uani 1 1 d . . . C15 C 0.6500(3) 0.2460(5) 0.4546(5) 0.0290(13) Uani 1 1 d . . . C16 C 0.7660(3) 0.0350(4) 0.7379(5) 0.0229(12) Uani 1 1 d . . . C17 C 0.7738(4) -0.0987(5) 0.9294(5) 0.0356(15) Uani 1 1 d . . . C18 C 0.8368(5) -0.0338(6) 1.0110(6) 0.0492(19) Uani 1 1 d . . . H18A H 0.8905 -0.0511 0.9778 0.074 Uiso 1 1 calc R . . H18B H 0.8343 -0.0543 1.1074 0.074 Uiso 1 1 calc R . . H18C H 0.8262 0.0460 1.0006 0.074 Uiso 1 1 calc R . . C19 C 0.7925(5) -0.2214(5) 0.9287(7) 0.0513(19) Uani 1 1 d . . . H19A H 0.7533 -0.2600 0.8686 0.077 Uiso 1 1 calc R . . H19B H 0.7893 -0.2509 1.0215 0.077 Uiso 1 1 calc R . . H19C H 0.8471 -0.2331 0.8956 0.077 Uiso 1 1 calc R . . C20 C 0.6898(4) -0.0769(7) 0.9780(6) 0.0498(19) Uani 1 1 d . . . H20A H 0.6805 0.0036 0.9823 0.075 Uiso 1 1 calc R . . H20B H 0.6842 -0.1092 1.0689 0.075 Uiso 1 1 calc R . . H20C H 0.6501 -0.1107 0.9145 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0518(11) 0.0672(11) 0.0463(10) 0.0047(8) 0.0185(8) -0.0105(9) O1 0.043(2) 0.040(2) 0.0177(18) -0.0049(16) -0.0038(18) 0.0042(18) O2 0.041(2) 0.029(2) 0.0172(18) -0.0002(15) 0.0018(17) -0.0015(17) O3 0.048(3) 0.044(2) 0.0124(17) -0.0001(17) 0.0047(18) 0.005(2) O4 0.052(3) 0.042(2) 0.0055(15) 0.0047(16) 0.0066(17) 0.0055(19) N1 0.026(2) 0.036(2) 0.019(2) 0.0005(19) -0.002(2) 0.0011(18) N2 0.041(3) 0.036(2) 0.0098(19) -0.0040(18) 0.000(2) 0.004(2) C1 0.031(3) 0.036(3) 0.013(2) -0.003(2) -0.005(3) 0.001(2) C2 0.035(3) 0.037(3) 0.007(2) 0.008(2) -0.007(3) -0.002(2) C3 0.067(5) 0.037(3) 0.036(3) 0.004(3) 0.010(4) -0.007(3) C4 0.058(4) 0.045(4) 0.037(3) 0.002(3) 0.019(4) -0.004(3) C5 0.039(4) 0.052(4) 0.025(3) 0.007(3) -0.002(3) -0.006(3) C6 0.069(5) 0.039(4) 0.062(5) -0.006(3) 0.021(4) -0.013(3) C7 0.051(4) 0.043(4) 0.050(5) -0.002(3) 0.013(4) -0.006(3) C8 0.037(3) 0.027(3) 0.015(2) 0.003(2) 0.002(2) -0.004(2) C9 0.035(3) 0.037(3) 0.010(2) -0.002(2) 0.001(2) 0.000(2) C10 0.043(4) 0.047(3) 0.020(3) -0.003(3) -0.006(3) -0.006(3) C11 0.038(3) 0.064(4) 0.021(3) -0.005(3) -0.008(3) -0.002(3) C12 0.040(3) 0.069(4) 0.024(3) 0.006(3) -0.008(3) 0.013(3) C13 0.043(3) 0.051(3) 0.019(3) 0.004(2) -0.001(3) 0.011(3) C14 0.038(3) 0.043(3) 0.015(3) 0.003(2) 0.002(3) -0.002(2) C15 0.037(3) 0.038(3) 0.012(2) 0.010(2) 0.004(2) -0.005(3) C16 0.025(3) 0.037(3) 0.006(2) 0.000(2) 0.001(2) -0.003(2) C17 0.051(4) 0.047(3) 0.010(2) 0.007(2) 0.003(3) 0.005(3) C18 0.066(4) 0.058(4) 0.023(3) 0.006(3) -0.010(3) 0.007(3) C19 0.083(5) 0.048(4) 0.022(3) 0.016(3) 0.006(4) 0.008(3) C20 0.053(4) 0.075(5) 0.022(3) 0.017(3) 0.007(3) 0.004(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 Cl1 C5 1.755(8) . ? O1 C8 1.207(7) . ? O2 C15 1.208(7) . ? O3 C16 1.211(6) . ? O4 C16 1.341(6) . ? O4 C17 1.503(6) . ? N1 C15 1.388(7) . ? N1 C8 1.408(6) . ? N1 C1 1.505(6) . ? N2 C16 1.375(7) . ? N2 C1 1.419(7) . ? C1 C2 1.519(8) . ? C2 C7 1.367(9) . ? C2 C3 1.391(9) . ? C3 C4 1.376(10) . ? C4 C5 1.341(9) . ? C5 C6 1.379(10) . ? C6 C7 1.397(11) . ? C8 C9 1.493(7) . ? C9 C14 1.373(8) . ? C9 C10 1.420(7) . ? C10 C11 1.387(9) . ? C11 C12 1.377(9) . ? C12 C13 1.406(8) . ? C13 C14 1.392(8) . ? C14 C15 1.510(7) . ? C17 C19 1.507(9) . ? C17 C20 1.509(10) . ? C17 C18 1.511(8) . ? 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 C16 O4 C17 120.7(4) . . ? C15 N1 C8 112.6(4) . . ? C15 N1 C1 122.6(4) . . ? C8 N1 C1 124.7(4) . . ? C16 N2 C1 121.4(5) . . ? N2 C1 N1 111.7(4) . . ? N2 C1 C2 113.4(5) . . ? N1 C1 C2 110.3(4) . . ? C7 C2 C3 118.2(6) . . ? C7 C2 C1 118.9(6) . . ? C3 C2 C1 122.9(5) . . ? C4 C3 C2 120.0(6) . . ? C5 C4 C3 121.0(7) . . ? C4 C5 C6 121.1(7) . . ? C4 C5 Cl1 119.7(6) . . ? C6 C5 Cl1 119.2(5) . . ? C5 C6 C7 117.8(7) . . ? C2 C7 C6 121.8(7) . . ? O1 C8 N1 125.4(4) . . ? O1 C8 C9 129.9(4) . . ? N1 C8 C9 104.6(4) . . ? C14 C9 C10 121.1(5) . . ? C14 C9 C8 109.6(4) . . ? C10 C9 C8 129.3(5) . . ? C11 C10 C9 116.1(6) . . ? C12 C11 C10 122.4(5) . . ? C11 C12 C13 121.6(5) . . ? C14 C13 C12 116.0(6) . . ? C9 C14 C13 122.7(5) . . ? C9 C14 C15 107.4(4) . . ? C13 C14 C15 129.9(5) . . ? O2 C15 N1 126.0(4) . . ? O2 C15 C14 128.3(5) . . ? N1 C15 C14 105.7(4) . . ? O3 C16 O4 127.1(5) . . ? O3 C16 N2 123.7(4) . . ? O4 C16 N2 109.2(5) . . ? O4 C17 C19 101.9(5) . . ? O4 C17 C20 111.4(4) . . ? C19 C17 C20 111.3(6) . . ? O4 C17 C18 108.4(5) . . ? C19 C17 C18 111.7(5) . . ? C20 C17 C18 111.7(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N2 C1 N1 -97.1(5) . . . . ? C16 N2 C1 C2 137.5(5) . . . . ? C15 N1 C1 N2 131.7(5) . . . . ? C8 N1 C1 N2 -49.9(7) . . . . ? C15 N1 C1 C2 -101.2(6) . . . . ? C8 N1 C1 C2 77.3(6) . . . . ? N2 C1 C2 C7 -143.1(5) . . . . ? N1 C1 C2 C7 90.7(5) . . . . ? N2 C1 C2 C3 37.7(5) . . . . ? N1 C1 C2 C3 -88.5(5) . . . . ? C7 C2 C3 C4 2.5(8) . . . . ? C1 C2 C3 C4 -178.3(5) . . . . ? C2 C3 C4 C5 -0.7(9) . . . . ? C3 C4 C5 C6 -1.2(9) . . . . ? C3 C4 C5 Cl1 178.1(5) . . . . ? C4 C5 C6 C7 1.2(9) . . . . ? Cl1 C5 C6 C7 -178.2(5) . . . . ? C3 C2 C7 C6 -2.5(8) . . . . ? C1 C2 C7 C6 178.3(5) . . . . ? C5 C6 C7 C2 0.7(10) . . . . ? C15 N1 C8 O1 177.0(6) . . . . ? C1 N1 C8 O1 -1.6(9) . . . . ? C15 N1 C8 C9 -1.6(6) . . . . ? C1 N1 C8 C9 179.8(5) . . . . ? O1 C8 C9 C14 -177.1(6) . . . . ? N1 C8 C9 C14 1.4(6) . . . . ? O1 C8 C9 C10 1.0(11) . . . . ? N1 C8 C9 C10 179.5(6) . . . . ? C14 C9 C10 C11 -2.2(9) . . . . ? C8 C9 C10 C11 179.9(6) . . . . ? C9 C10 C11 C12 1.1(10) . . . . ? C10 C11 C12 C13 0.6(11) . . . . ? C11 C12 C13 C14 -1.2(10) . . . . ? C10 C9 C14 C13 1.7(9) . . . . ? C8 C9 C14 C13 180.0(5) . . . . ? C10 C9 C14 C15 -179.0(5) . . . . ? C8 C9 C14 C15 -0.7(6) . . . . ? C12 C13 C14 C9 0.1(9) . . . . ? C12 C13 C14 C15 -179.1(6) . . . . ? C8 N1 C15 O2 -178.9(5) . . . . ? C1 N1 C15 O2 -0.3(9) . . . . ? C8 N1 C15 C14 1.2(6) . . . . ? C1 N1 C15 C14 179.8(5) . . . . ? C9 C14 C15 O2 179.8(6) . . . . ? C13 C14 C15 O2 -0.9(10) . . . . ? C9 C14 C15 N1 -0.3(6) . . . . ? C13 C14 C15 N1 179.0(6) . . . . ? C17 O4 C16 O3 -6.5(8) . . . . ? C17 O4 C16 N2 173.3(4) . . . . ? C1 N2 C16 O3 2.1(8) . . . . ? C1 N2 C16 O4 -177.7(4) . . . . ? C16 O4 C17 C19 178.0(5) . . . . ? C16 O4 C17 C20 59.3(7) . . . . ? C16 O4 C17 C18 -64.1(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O2 0.88 2.12 2.992(6) 172.5 4_646 _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.874 _refine_diff_density_max 0.516 _refine_diff_density_min -0.816 _refine_diff_density_rms 0.111 data_clam1 _database_code_depnum_ccdc_archive 'CCDC 656233' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H19 Cl N2 O4' _chemical_formula_weight 386.82 _chemical_absolute_configuration R 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.534(6) _cell_length_b 12.015(4) _cell_length_c 9.785(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.860(6) _cell_angle_gamma 90.00 _cell_volume 1942.7(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2998 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 25.22 _exptl_crystal_description parallelepip _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.060 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4683 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.1074 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.25 _reflns_number_total 3258 _reflns_number_gt 2520 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1191P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.13(11) _refine_ls_number_reflns 3258 _refine_ls_number_parameters 247 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.1688 _refine_ls_wR_factor_gt 0.1554 _refine_ls_goodness_of_fit_ref 0.848 _refine_ls_restrained_S_all 0.848 _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 C1 C 0.2223(2) 0.6296(3) 0.9677(4) 0.0227(8) Uani 1 1 d . . . H1 H 0.2247 0.6962 0.9004 0.034 Uiso 1 1 d R . . N11 N 0.29993(19) 0.6366(3) 1.0490(3) 0.0231(7) Uani 1 1 d . . . O11 O 0.33768(16) 0.8122(2) 0.9780(3) 0.0268(6) Uani 1 1 d . . . O12 O 0.29675(17) 0.4682(2) 1.1644(3) 0.0307(7) Uani 1 1 d . . . C11 C 0.3506(2) 0.7307(4) 1.0456(4) 0.0227(8) Uani 1 1 d . . . C12 C 0.4210(2) 0.7036(3) 1.1400(4) 0.0277(9) Uani 1 1 d . . . C13 C 0.4892(3) 0.7665(4) 1.1727(4) 0.0349(11) Uani 1 1 d . . . H13 H 0.4974 0.8381 1.1344 0.042 Uiso 1 1 calc R . . C14 C 0.5454(3) 0.7186(4) 1.2652(4) 0.0393(11) Uani 1 1 d . . . H14 H 0.5931 0.7588 1.2902 0.047 Uiso 1 1 calc R . . C15 C 0.5334(3) 0.6154(5) 1.3208(4) 0.0409(12) Uani 1 1 d . . . H15 H 0.5732 0.5858 1.3829 0.049 Uiso 1 1 calc R . . C16 C 0.4645(2) 0.5529(4) 1.2887(4) 0.0328(10) Uani 1 1 d . . . H16 H 0.4558 0.4821 1.3289 0.039 Uiso 1 1 calc R . . C17 C 0.4088(2) 0.5988(4) 1.1950(4) 0.0255(9) Uani 1 1 d . . . C18 C 0.3295(2) 0.5547(3) 1.1390(4) 0.0236(8) Uani 1 1 d . . . N21 N 0.2145(2) 0.5273(3) 0.8969(3) 0.0250(8) Uani 1 1 d . . . H21 H 0.2050 0.4630 0.9534 0.038 Uiso 1 1 d R . . O21 O 0.25997(17) 0.5953(3) 0.6960(3) 0.0323(7) Uani 1 1 d . . . O22 O 0.21936(17) 0.4148(2) 0.7185(3) 0.0306(7) Uani 1 1 d . . . C21 C 0.2344(2) 0.5187(3) 0.7619(4) 0.0229(9) Uani 1 1 d . . . C22 C 0.2257(3) 0.3853(4) 0.5726(4) 0.0342(10) Uani 1 1 d . . . C23 C 0.1631(3) 0.4504(4) 0.4881(5) 0.0449(12) Uani 1 1 d . . . H23A H 0.1088 0.4322 0.5187 0.067 Uiso 1 1 calc R . . H23B H 0.1672 0.4307 0.3914 0.067 Uiso 1 1 calc R . . H23C H 0.1729 0.5303 0.4998 0.067 Uiso 1 1 calc R . . C24 C 0.3100(3) 0.4074(5) 0.5218(5) 0.0466(13) Uani 1 1 d . . . H24A H 0.3186 0.4878 0.5144 0.070 Uiso 1 1 calc R . . H24B H 0.3155 0.3729 0.4318 0.070 Uiso 1 1 calc R . . H24C H 0.3503 0.3757 0.5863 0.070 Uiso 1 1 calc R . . C25 C 0.2067(4) 0.2628(4) 0.5713(5) 0.0474(13) Uani 1 1 d . . . H25A H 0.2440 0.2240 0.6350 0.071 Uiso 1 1 calc R . . H25B H 0.2129 0.2333 0.4789 0.071 Uiso 1 1 calc R . . H25C H 0.1510 0.2513 0.5993 0.071 Uiso 1 1 calc R . . C31 C 0.1510(2) 0.6530(3) 1.0595(4) 0.0228(9) Uani 1 1 d . . . C32 C 0.1133(3) 0.5713(4) 1.1312(5) 0.0440(12) Uani 1 1 d . . . H32 H 0.1326 0.4969 1.1270 0.053 Uiso 1 1 calc R . . C33 C 0.0478(3) 0.5955(4) 1.2096(5) 0.0450(12) Uani 1 1 d . . . H33 H 0.0216 0.5378 1.2576 0.054 Uiso 1 1 calc R . . C34 C 0.0205(3) 0.7021(4) 1.2183(4) 0.0341(11) Uani 1 1 d . . . C35 C 0.0588(3) 0.7860(5) 1.1498(6) 0.0554(15) Uani 1 1 d . . . H35 H 0.0404 0.8606 1.1562 0.066 Uiso 1 1 calc R . . C36 C 0.1246(3) 0.7603(4) 1.0713(6) 0.0441(12) Uani 1 1 d . . . H36 H 0.1517 0.8181 1.0249 0.053 Uiso 1 1 calc R . . Cl31 Cl -0.06413(7) 0.73083(11) 1.31444(14) 0.0514(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0162(19) 0.027(2) 0.0245(18) 0.0035(16) -0.0070(15) 0.0001(15) N11 0.0171(17) 0.0254(19) 0.0265(16) -0.0005(14) -0.0048(13) -0.0018(13) O11 0.0257(14) 0.0241(16) 0.0303(14) -0.0003(13) -0.0014(11) 0.0002(12) O12 0.0332(17) 0.0269(17) 0.0315(15) 0.0050(12) -0.0072(12) -0.0035(13) C11 0.0213(18) 0.026(2) 0.0213(18) -0.0060(18) 0.0028(14) 0.0013(17) C12 0.022(2) 0.035(3) 0.0254(19) -0.0064(18) -0.0017(16) 0.0026(17) C13 0.027(2) 0.046(3) 0.031(2) -0.0057(19) -0.0034(18) -0.0071(19) C14 0.026(2) 0.059(3) 0.032(2) -0.007(2) -0.0065(17) -0.007(2) C15 0.024(2) 0.065(3) 0.033(2) 0.002(2) -0.0099(18) 0.007(2) C16 0.026(2) 0.044(3) 0.029(2) 0.0014(19) -0.0017(17) 0.0039(19) C17 0.022(2) 0.034(2) 0.0208(18) -0.0041(16) -0.0017(15) 0.0034(17) C18 0.023(2) 0.024(2) 0.0231(18) -0.0019(16) 0.0004(15) 0.0038(16) N21 0.0234(18) 0.0301(19) 0.0214(16) 0.0008(14) -0.0030(13) -0.0020(14) O21 0.0346(16) 0.0371(18) 0.0253(14) 0.0007(13) 0.0008(12) -0.0042(14) O22 0.0358(16) 0.0339(18) 0.0223(13) -0.0059(12) 0.0019(12) -0.0046(13) C21 0.0141(19) 0.031(2) 0.0232(19) 0.0001(17) -0.0037(15) 0.0014(16) C22 0.035(2) 0.044(3) 0.023(2) -0.0101(18) 0.0021(18) -0.003(2) C23 0.046(3) 0.051(3) 0.036(2) -0.006(2) -0.011(2) -0.004(2) C24 0.035(3) 0.070(4) 0.035(2) -0.014(3) 0.006(2) -0.003(2) C25 0.069(3) 0.043(3) 0.031(2) -0.013(2) 0.004(2) -0.009(2) C31 0.023(2) 0.025(2) 0.0197(18) -0.0044(15) -0.0082(15) 0.0001(16) C32 0.046(3) 0.034(3) 0.053(3) 0.001(2) 0.013(2) 0.003(2) C33 0.042(3) 0.040(3) 0.053(3) 0.001(2) 0.020(2) -0.001(2) C34 0.023(2) 0.043(3) 0.036(2) -0.002(2) 0.0002(18) 0.0051(19) C35 0.052(3) 0.034(3) 0.081(4) 0.007(3) 0.023(3) 0.012(2) C36 0.037(3) 0.037(3) 0.058(3) 0.007(2) 0.015(2) 0.002(2) Cl31 0.0336(6) 0.0617(9) 0.0600(8) -0.0034(6) 0.0186(5) 0.0095(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N21 1.415(5) . ? C1 N11 1.490(4) . ? C1 C31 1.531(6) . ? C1 H1 1.0370 . ? N11 C18 1.398(5) . ? N11 C11 1.408(5) . ? O11 C11 1.197(5) . ? O12 C18 1.202(5) . ? C11 C12 1.499(5) . ? C12 C17 1.386(6) . ? C12 C13 1.387(6) . ? C13 C14 1.399(6) . ? C13 H13 0.9500 . ? C14 C15 1.371(7) . ? C14 H14 0.9500 . ? C15 C16 1.393(7) . ? C15 H15 0.9500 . ? C16 C17 1.392(6) . ? C16 H16 0.9500 . ? C17 C18 1.501(6) . ? N21 C21 1.375(5) . ? N21 H21 0.9655 . ? O21 C21 1.208(5) . ? O22 C21 1.339(5) . ? O22 C22 1.478(5) . ? C22 C25 1.505(7) . ? C22 C24 1.518(6) . ? C22 C23 1.521(7) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C31 C36 1.367(7) . ? C31 C32 1.369(6) . ? C32 C33 1.379(7) . ? C32 H32 0.9500 . ? C33 C34 1.362(7) . ? C33 H33 0.9500 . ? C34 C35 1.375(7) . ? C34 Cl31 1.746(4) . ? C35 C36 1.386(7) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N21 C1 N11 111.9(3) . . ? N21 C1 C31 112.8(3) . . ? N11 C1 C31 110.0(3) . . ? N21 C1 H1 111.3 . . ? N11 C1 H1 104.2 . . ? C31 C1 H1 106.0 . . ? C18 N11 C11 112.6(3) . . ? C18 N11 C1 125.0(3) . . ? C11 N11 C1 122.4(3) . . ? O11 C11 N11 125.1(3) . . ? O11 C11 C12 129.8(4) . . ? N11 C11 C12 105.2(3) . . ? C17 C12 C13 122.2(4) . . ? C17 C12 C11 108.5(3) . . ? C13 C12 C11 129.3(4) . . ? C12 C13 C14 116.3(4) . . ? C12 C13 H13 121.8 . . ? C14 C13 H13 121.8 . . ? C15 C14 C13 121.7(4) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C14 C15 C16 121.8(4) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C17 C16 C15 116.9(4) . . ? C17 C16 H16 121.5 . . ? C15 C16 H16 121.5 . . ? C12 C17 C16 121.0(4) . . ? C12 C17 C18 108.4(3) . . ? C16 C17 C18 130.6(4) . . ? O12 C18 N11 126.0(4) . . ? O12 C18 C17 128.6(4) . . ? N11 C18 C17 105.4(3) . . ? C21 N21 C1 121.0(3) . . ? C21 N21 H21 122.5 . . ? C1 N21 H21 115.4 . . ? C21 O22 C22 120.8(3) . . ? O21 C21 O22 127.3(3) . . ? O21 C21 N21 123.6(4) . . ? O22 C21 N21 109.1(3) . . ? O22 C22 C25 102.8(4) . . ? O22 C22 C24 111.7(3) . . ? C25 C22 C24 111.2(5) . . ? O22 C22 C23 109.5(4) . . ? C25 C22 C23 111.1(4) . . ? C24 C22 C23 110.4(4) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C36 C31 C32 118.7(4) . . ? C36 C31 C1 118.5(4) . . ? C32 C31 C1 122.8(4) . . ? C31 C32 C33 120.9(5) . . ? C31 C32 H32 119.6 . . ? C33 C32 H32 119.6 . . ? C34 C33 C32 120.1(5) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 120.0(4) . . ? C33 C34 Cl31 119.5(4) . . ? C35 C34 Cl31 120.5(4) . . ? C34 C35 C36 119.3(5) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 120.4 . . ? C31 C36 C35 121.0(5) . . ? C31 C36 H36 119.5 . . ? C35 C36 H36 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N21 C1 N11 C18 -49.5(5) . . . . ? C31 C1 N11 C18 76.7(4) . . . . ? N21 C1 N11 C11 132.6(3) . . . . ? C31 C1 N11 C11 -101.1(4) . . . . ? C18 N11 C11 O11 -179.0(3) . . . . ? C1 N11 C11 O11 -0.8(6) . . . . ? C18 N11 C11 C12 2.1(4) . . . . ? C1 N11 C11 C12 -179.8(3) . . . . ? O11 C11 C12 C17 -179.8(4) . . . . ? N11 C11 C12 C17 -0.9(4) . . . . ? O11 C11 C12 C13 0.0(7) . . . . ? N11 C11 C12 C13 178.9(4) . . . . ? C17 C12 C13 C14 -0.2(6) . . . . ? C11 C12 C13 C14 180.0(4) . . . . ? C12 C13 C14 C15 -0.3(7) . . . . ? C13 C14 C15 C16 -0.3(7) . . . . ? C14 C15 C16 C17 1.4(7) . . . . ? C13 C12 C17 C16 1.3(6) . . . . ? C11 C12 C17 C16 -178.9(3) . . . . ? C13 C12 C17 C18 179.7(4) . . . . ? C11 C12 C17 C18 -0.5(4) . . . . ? C15 C16 C17 C12 -1.8(6) . . . . ? C15 C16 C17 C18 -179.8(4) . . . . ? C11 N11 C18 O12 177.4(4) . . . . ? C1 N11 C18 O12 -0.6(6) . . . . ? C11 N11 C18 C17 -2.3(4) . . . . ? C1 N11 C18 C17 179.6(3) . . . . ? C12 C17 C18 O12 -178.1(4) . . . . ? C16 C17 C18 O12 0.1(7) . . . . ? C12 C17 C18 N11 1.7(4) . . . . ? C16 C17 C18 N11 179.9(4) . . . . ? N11 C1 N21 C21 -96.9(4) . . . . ? C31 C1 N21 C21 138.4(3) . . . . ? C22 O22 C21 O21 -6.2(6) . . . . ? C22 O22 C21 N21 172.5(3) . . . . ? C1 N21 C21 O21 0.6(6) . . . . ? C1 N21 C21 O22 -178.2(3) . . . . ? C21 O22 C22 C25 178.3(4) . . . . ? C21 O22 C22 C24 59.0(5) . . . . ? C21 O22 C22 C23 -63.5(5) . . . . ? N21 C1 C31 C36 -143.5(4) . . . . ? N11 C1 C31 C36 90.7(4) . . . . ? N21 C1 C31 C32 37.3(5) . . . . ? N11 C1 C31 C32 -88.5(4) . . . . ? C36 C31 C32 C33 2.7(7) . . . . ? C1 C31 C32 C33 -178.1(4) . . . . ? C31 C32 C33 C34 -1.1(8) . . . . ? C32 C33 C34 C35 -0.6(8) . . . . ? C32 C33 C34 Cl31 178.4(4) . . . . ? C33 C34 C35 C36 0.7(8) . . . . ? Cl31 C34 C35 C36 -178.3(4) . . . . ? C32 C31 C36 C35 -2.6(7) . . . . ? C1 C31 C36 C35 178.1(4) . . . . ? C34 C35 C36 C31 1.0(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N21 H21 O11 0.97 2.07 2.999(4) 162.1 4_547 N21 H21 O12 0.97 2.52 2.995(4) 110.1 . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.434 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.078