# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Linda Shimizu' _publ_contact_author_email SHIMIZUL@MAIL.CHEM.SC.EDU _publ_section_title ; Manipulating the cavity of a porous material changes the photoreactivity of included guests ; loop_ _publ_author_name 'Linda Shimizu' 'Mahender B. Dewal' 'Fiaz Mohammed' 'Mark D Smith' 'Yuewen Xu.' 'Jun Yang.' # Attachment 'md01066.cif' data_md01066 _database_code_depnum_ccdc_archive 'CCDC 684399' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H50 N6 O4, 2(C H Cl3)' _chemical_formula_sum 'C46 H52 Cl6 N6 O4' _chemical_formula_weight 965.64 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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 11.4583(6) _cell_length_b 22.4576(12) _cell_length_c 9.6210(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.5050(10) _cell_angle_gamma 90.00 _cell_volume 2396.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 2163 _cell_measurement_theta_min 2.367 _cell_measurement_theta_max 18.811 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.407 _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 150(1) _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 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 19646 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 22.54 _reflns_number_total 3152 _reflns_number_gt 1978 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.625 (Bruker, 1998)' _computing_cell_refinement 'SAINT+ NT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT+ NT V6.22' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V6.1 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V6.1' _refine_special_details ; 30 C-Cl and Cl-Cl distances restraints used to model CHCl3 disorder. 023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 22.54 Deg. 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 22.54 Deg. RESPONSE: No high-angle X-ray diffraction observed due to the combined effects of small available crystal size and solvent disorder. 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^)+(0.0519P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3152 _refine_ls_number_parameters 307 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1148 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_restrained_S_all 0.913 _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 C1 C 0.2805(3) 0.31956(14) 0.2471(4) 0.0352(9) Uani 1 1 d . . . C2 C 0.2144(3) 0.28629(15) 0.4588(4) 0.0420(9) Uani 1 1 d . . . H2A H 0.1568 0.2528 0.4332 0.050 Uiso 1 1 calc R . . H2B H 0.2593 0.2816 0.5604 0.050 Uiso 1 1 calc R . . C3 C 0.0837(3) 0.34555(16) 0.2891(3) 0.0435(9) Uani 1 1 d . . . H3A H 0.0300 0.3106 0.2635 0.052 Uiso 1 1 calc R . . H3B H 0.0335 0.3820 0.2715 0.052 Uiso 1 1 calc R . . C4 C 0.4100(3) 0.25280(15) 0.4160(4) 0.0418(9) Uani 1 1 d . . . H4A H 0.4438 0.2449 0.3327 0.050 Uiso 1 1 calc R . . H4B H 0.3915 0.2139 0.4537 0.050 Uiso 1 1 calc R . . C5 C 0.5049(3) 0.28347(15) 0.5305(3) 0.0370(9) Uani 1 1 d . . . C6 C 0.6119(3) 0.25358(16) 0.5895(4) 0.0487(10) Uani 1 1 d . . . H6 H 0.6240 0.2148 0.5560 0.058 Uiso 1 1 calc R . . C7 C 0.7001(3) 0.27914(17) 0.6953(4) 0.0552(11) Uani 1 1 d . . . H7 H 0.7719 0.2575 0.7355 0.066 Uiso 1 1 calc R . . C8 C 0.6864(3) 0.33632(16) 0.7450(4) 0.0458(10) Uani 1 1 d . . . C9 C 0.5791(3) 0.36608(15) 0.6861(4) 0.0446(10) Uani 1 1 d . . . H9 H 0.5674 0.4051 0.7182 0.054 Uiso 1 1 calc R . . C10 C 0.4892(3) 0.33960(15) 0.5812(4) 0.0406(9) Uani 1 1 d . . . H10 H 0.4157 0.3603 0.5436 0.049 Uiso 1 1 calc R . . C11 C 0.7829(3) 0.36249(17) 0.8616(5) 0.0575(11) Uani 1 1 d . . . C12 C 0.7987(3) 0.42845(16) 0.8734(4) 0.0443(10) Uani 1 1 d . . . C13 C 0.8403(3) 0.45380(17) 1.0086(4) 0.0497(10) Uani 1 1 d . . . H13 H 0.8568 0.4292 1.0916 0.060 Uiso 1 1 calc R . . C14 C 0.8576(3) 0.51392(16) 1.0227(4) 0.0435(9) Uani 1 1 d . . . H14 H 0.8860 0.5305 1.1160 0.052 Uiso 1 1 calc R . . C15 C 0.8346(3) 0.55159(15) 0.9036(4) 0.0354(9) Uani 1 1 d . . . C16 C 0.7944(3) 0.52602(16) 0.7699(4) 0.0410(9) Uani 1 1 d . . . H16 H 0.7792 0.5505 0.6868 0.049 Uiso 1 1 calc R . . C17 C 0.7758(3) 0.46524(16) 0.7546(4) 0.0441(9) Uani 1 1 d . . . H17 H 0.7469 0.4486 0.6615 0.053 Uiso 1 1 calc R . . C18 C 0.8551(3) 0.61756(15) 0.9264(3) 0.0416(9) Uani 1 1 d . . . H18A H 0.8047 0.6319 0.9895 0.050 Uiso 1 1 calc R . . H18B H 0.9404 0.6240 0.9779 0.050 Uiso 1 1 calc R . . C19 C 0.0760(3) 0.35456(16) 0.5455(4) 0.0458(10) Uani 1 1 d . . . C20 C 0.1633(4) 0.3522(2) 0.6951(4) 0.0774(14) Uani 1 1 d . . . H20A H 0.1947 0.3117 0.7147 0.116 Uiso 1 1 calc R . . H20B H 0.1206 0.3637 0.7674 0.116 Uiso 1 1 calc R . . H20C H 0.2303 0.3798 0.6989 0.116 Uiso 1 1 calc R . . C21 C 0.0250(3) 0.41808(15) 0.5207(4) 0.0509(10) Uani 1 1 d . . . H21A H 0.0912 0.4464 0.5267 0.076 Uiso 1 1 calc R . . H21B H -0.0178 0.4277 0.5942 0.076 Uiso 1 1 calc R . . H21C H -0.0310 0.4206 0.4255 0.076 Uiso 1 1 calc R . . C22 C -0.0260(4) 0.30866(18) 0.5344(5) 0.0781(14) Uani 1 1 d . . . H22A H -0.0805 0.3102 0.4381 0.117 Uiso 1 1 calc R . . H22B H -0.0711 0.3179 0.6059 0.117 Uiso 1 1 calc R . . H22C H 0.0087 0.2687 0.5523 0.117 Uiso 1 1 calc R . . N1 N 0.2983(2) 0.28565(12) 0.3664(3) 0.0373(7) Uani 1 1 d . . . N2 N 0.1714(2) 0.34649(12) 0.2025(3) 0.0380(7) Uani 1 1 d . . . N3 N 0.1497(2) 0.34243(12) 0.4396(3) 0.0368(7) Uani 1 1 d . . . O1 O 0.3582(2) 0.32430(10) 0.1781(2) 0.0466(7) Uani 1 1 d . . . O2 O 0.8498(2) 0.33030(12) 0.9504(3) 0.0890(11) Uani 1 1 d . . . C23A C 0.435(2) 0.5853(4) 0.7344(10) 0.0598(15) Uani 0.50 1 d PD A 1 H23A H 0.4995 0.6152 0.7343 0.072 Uiso 0.50 1 calc PR A 1 Cl1A Cl 0.296(4) 0.6180(16) 0.6605(14) 0.0862(19) Uani 0.50 1 d PD A 1 Cl2A Cl 0.4547(5) 0.5248(3) 0.6310(7) 0.0908(14) Uani 0.50 1 d PD A 1 Cl3A Cl 0.4463(8) 0.5630(4) 0.9091(9) 0.167(4) Uani 0.50 1 d PD A 1 C23B C 0.438(2) 0.5882(4) 0.7609(9) 0.0598(15) Uani 0.50 1 d PD B 2 H23B H 0.5057 0.6135 0.7468 0.072 Uiso 0.50 1 calc PR B 2 Cl1B Cl 0.303(4) 0.6231(16) 0.6803(14) 0.0862(19) Uani 0.50 1 d PD B 2 Cl2B Cl 0.4447(9) 0.5199(4) 0.6799(9) 0.186(5) Uani 0.50 1 d PD B 2 Cl3B Cl 0.4540(5) 0.5787(3) 0.9427(7) 0.0751(12) Uani 0.50 1 d PD B 2 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 0.038(2) 0.032(2) 0.035(2) -0.0092(18) 0.009(2) -0.0062(18) C2 0.045(2) 0.036(2) 0.045(2) 0.0049(18) 0.0119(19) 0.0050(18) C3 0.048(2) 0.045(2) 0.035(2) 0.0043(18) 0.0040(19) 0.0017(18) C4 0.043(2) 0.035(2) 0.047(2) -0.0014(18) 0.0111(19) 0.0042(18) C5 0.032(2) 0.035(2) 0.044(2) 0.0051(18) 0.0097(18) 0.0018(17) C6 0.042(2) 0.031(2) 0.069(3) 0.001(2) 0.006(2) 0.0023(19) C7 0.038(2) 0.037(3) 0.085(3) 0.016(2) 0.003(2) 0.0043(19) C8 0.035(2) 0.034(2) 0.063(3) 0.012(2) 0.001(2) -0.0056(19) C9 0.043(2) 0.035(2) 0.051(2) 0.0046(19) 0.005(2) -0.0015(19) C10 0.031(2) 0.037(2) 0.051(2) 0.0013(19) 0.0050(18) 0.0003(17) C11 0.042(2) 0.039(3) 0.081(3) 0.015(2) -0.004(2) -0.006(2) C12 0.029(2) 0.040(2) 0.058(3) 0.008(2) -0.0004(19) -0.0031(17) C13 0.040(2) 0.052(3) 0.050(3) 0.020(2) -0.001(2) -0.0064(19) C14 0.043(2) 0.049(3) 0.034(2) 0.0069(19) 0.0017(18) -0.0011(19) C15 0.032(2) 0.040(2) 0.033(2) 0.0044(18) 0.0066(17) -0.0025(17) C16 0.044(2) 0.041(2) 0.034(2) 0.0062(18) 0.0013(18) -0.0053(18) C17 0.042(2) 0.040(2) 0.045(2) -0.001(2) 0.0017(18) -0.0079(18) C18 0.051(2) 0.043(2) 0.028(2) 0.0010(18) 0.0031(18) 0.0008(18) C19 0.053(2) 0.042(2) 0.048(2) 0.0038(19) 0.023(2) 0.0082(19) C20 0.117(4) 0.092(4) 0.025(2) 0.002(2) 0.020(2) 0.043(3) C21 0.057(2) 0.048(3) 0.051(2) 0.0051(19) 0.018(2) 0.014(2) C22 0.074(3) 0.063(3) 0.112(4) 0.013(3) 0.051(3) 0.000(2) N1 0.0423(18) 0.0358(17) 0.0339(17) 0.0038(15) 0.0095(15) 0.0029(14) N2 0.0416(19) 0.0403(18) 0.0304(17) 0.0019(14) 0.0060(15) 0.0015(15) N3 0.0410(17) 0.0335(18) 0.0331(17) 0.0020(13) 0.0043(14) 0.0006(14) O1 0.0489(16) 0.0501(17) 0.0440(15) -0.0046(12) 0.0176(13) -0.0035(12) O2 0.067(2) 0.0439(18) 0.122(3) 0.0243(17) -0.0403(19) -0.0113(15) C23A 0.050(3) 0.060(3) 0.069(4) 0.009(3) 0.016(4) -0.004(2) Cl1A 0.068(3) 0.083(4) 0.099(3) -0.007(3) 0.007(4) 0.019(4) Cl2A 0.074(2) 0.065(3) 0.125(3) 0.009(2) 0.008(2) 0.0268(18) Cl3A 0.177(6) 0.220(9) 0.100(5) 0.061(5) 0.029(4) -0.037(5) C23B 0.050(3) 0.060(3) 0.069(4) 0.009(3) 0.016(4) -0.004(2) Cl1B 0.068(3) 0.083(4) 0.099(3) -0.007(3) 0.007(4) 0.019(4) Cl2B 0.213(7) 0.119(6) 0.215(8) -0.063(6) 0.033(5) 0.076(5) Cl3B 0.059(2) 0.086(2) 0.080(3) 0.034(2) 0.0184(18) 0.0035(17) _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 O1 1.241(4) . ? C1 N1 1.350(4) . ? C1 N2 1.358(4) . ? C2 N3 1.451(4) . ? C2 N1 1.463(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.458(4) . ? C3 N3 1.458(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.451(4) . ? C4 C5 1.506(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.380(4) . ? C5 C6 1.388(4) . ? C6 C7 1.368(5) . ? C6 H6 0.9500 . ? C7 C8 1.393(5) . ? C7 H7 0.9500 . ? C8 C9 1.389(4) . ? C8 C11 1.485(5) . ? C9 C10 1.383(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 O2 1.230(4) . ? C11 C12 1.493(5) . ? C12 C17 1.382(5) . ? C12 C13 1.390(5) . ? C13 C14 1.366(5) . ? C13 H13 0.9500 . ? C14 C15 1.395(4) . ? C14 H14 0.9500 . ? C15 C16 1.379(4) . ? C15 C18 1.507(4) . ? C16 C17 1.384(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 N2 1.447(4) 3_666 ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 N3 1.502(4) . ? C19 C20 1.535(5) . ? C19 C21 1.538(5) . ? C19 C22 1.542(5) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N2 C18 1.447(4) 3_666 ? C23A Cl3A 1.726(5) . ? C23A Cl1A 1.732(5) . ? C23A Cl2A 1.733(5) . ? C23A H23A 1.0000 . ? C23B Cl3B 1.725(5) . ? C23B Cl1B 1.731(5) . ? C23B Cl2B 1.732(5) . ? C23B H23B 1.0000 . ? 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 C1 N1 121.9(3) . . ? O1 C1 N2 121.3(3) . . ? N1 C1 N2 116.8(3) . . ? N3 C2 N1 108.9(3) . . ? N3 C2 H2A 109.9 . . ? N1 C2 H2A 109.9 . . ? N3 C2 H2B 109.9 . . ? N1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? N2 C3 N3 107.9(3) . . ? N2 C3 H3A 110.1 . . ? N3 C3 H3A 110.1 . . ? N2 C3 H3B 110.1 . . ? N3 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? N1 C4 C5 115.1(3) . . ? N1 C4 H4A 108.5 . . ? C5 C4 H4A 108.5 . . ? N1 C4 H4B 108.5 . . ? C5 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? C10 C5 C6 118.5(3) . . ? C10 C5 C4 122.8(3) . . ? C6 C5 C4 118.7(3) . . ? C7 C6 C5 120.9(3) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 121.1(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 117.9(3) . . ? C9 C8 C11 122.2(3) . . ? C7 C8 C11 119.9(3) . . ? C10 C9 C8 120.8(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C5 C10 C9 120.8(3) . . ? C5 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? O2 C11 C8 120.6(3) . . ? O2 C11 C12 119.2(3) . . ? C8 C11 C12 120.2(3) . . ? C17 C12 C13 118.6(3) . . ? C17 C12 C11 122.4(4) . . ? C13 C12 C11 119.0(3) . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 121.6(3) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C16 C15 C14 117.7(3) . . ? C16 C15 C18 123.3(3) . . ? C14 C15 C18 119.1(3) . . ? C15 C16 C17 121.1(3) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C12 C17 C16 120.6(3) . . ? C12 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? N2 C18 C15 115.6(3) 3_666 . ? N2 C18 H18A 108.4 3_666 . ? C15 C18 H18A 108.4 . . ? N2 C18 H18B 108.4 3_666 . ? C15 C18 H18B 108.4 . . ? H18A C18 H18B 107.4 . . ? N3 C19 C20 106.6(3) . . ? N3 C19 C21 108.7(3) . . ? C20 C19 C21 108.1(3) . . ? N3 C19 C22 112.2(3) . . ? C20 C19 C22 110.3(3) . . ? C21 C19 C22 110.9(3) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C1 N1 C4 119.9(3) . . ? C1 N1 C2 121.9(3) . . ? C4 N1 C2 117.7(3) . . ? C1 N2 C18 119.9(3) . 3_666 ? C1 N2 C3 121.7(3) . . ? C18 N2 C3 118.1(3) 3_666 . ? C2 N3 C3 106.8(3) . . ? C2 N3 C19 115.3(3) . . ? C3 N3 C19 115.1(3) . . ? Cl3A C23A Cl1A 111.2(5) . . ? Cl3A C23A Cl2A 110.0(4) . . ? Cl1A C23A Cl2A 109.6(4) . . ? Cl3A C23A H23A 108.6 . . ? Cl1A C23A H23A 108.7 . . ? Cl2A C23A H23A 108.6 . . ? Cl3B C23B Cl1B 111.6(5) . . ? Cl3B C23B Cl2B 109.9(4) . . ? Cl1B C23B Cl2B 109.6(4) . . ? Cl3B C23B H23B 108.6 . . ? Cl1B C23B H23B 108.6 . . ? Cl2B C23B H23B 108.6 . . ? 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 N1 C4 C5 C10 -2.4(5) . . . . ? N1 C4 C5 C6 176.4(3) . . . . ? C10 C5 C6 C7 -0.2(5) . . . . ? C4 C5 C6 C7 -179.0(3) . . . . ? C5 C6 C7 C8 -1.3(6) . . . . ? C6 C7 C8 C9 1.5(6) . . . . ? C6 C7 C8 C11 179.0(3) . . . . ? C7 C8 C9 C10 -0.2(5) . . . . ? C11 C8 C9 C10 -177.6(3) . . . . ? C6 C5 C10 C9 1.5(5) . . . . ? C4 C5 C10 C9 -179.7(3) . . . . ? C8 C9 C10 C5 -1.3(5) . . . . ? C9 C8 C11 O2 149.7(4) . . . . ? C7 C8 C11 O2 -27.7(6) . . . . ? C9 C8 C11 C12 -29.4(5) . . . . ? C7 C8 C11 C12 153.1(4) . . . . ? O2 C11 C12 C17 147.5(4) . . . . ? C8 C11 C12 C17 -33.3(5) . . . . ? O2 C11 C12 C13 -31.2(5) . . . . ? C8 C11 C12 C13 148.0(4) . . . . ? C17 C12 C13 C14 0.2(5) . . . . ? C11 C12 C13 C14 178.9(3) . . . . ? C12 C13 C14 C15 -0.1(5) . . . . ? C13 C14 C15 C16 -0.5(5) . . . . ? C13 C14 C15 C18 179.8(3) . . . . ? C14 C15 C16 C17 1.0(5) . . . . ? C18 C15 C16 C17 -179.3(3) . . . . ? C13 C12 C17 C16 0.3(5) . . . . ? C11 C12 C17 C16 -178.4(3) . . . . ? C15 C16 C17 C12 -0.9(5) . . . . ? C16 C15 C18 N2 0.5(5) . . . 3_666 ? C14 C15 C18 N2 -179.7(3) . . . 3_666 ? O1 C1 N1 C4 -0.9(5) . . . . ? N2 C1 N1 C4 176.5(3) . . . . ? O1 C1 N1 C2 171.5(3) . . . . ? N2 C1 N1 C2 -11.1(4) . . . . ? C5 C4 N1 C1 95.8(4) . . . . ? C5 C4 N1 C2 -76.9(4) . . . . ? N3 C2 N1 C1 -24.1(4) . . . . ? N3 C2 N1 C4 148.5(3) . . . . ? O1 C1 N2 C18 -1.2(5) . . . 3_666 ? N1 C1 N2 C18 -178.6(3) . . . 3_666 ? O1 C1 N2 C3 -174.5(3) . . . . ? N1 C1 N2 C3 8.1(4) . . . . ? N3 C3 N2 C1 29.5(4) . . . . ? N3 C3 N2 C18 -143.9(3) . . . 3_666 ? N1 C2 N3 C3 61.0(3) . . . . ? N1 C2 N3 C19 -169.7(3) . . . . ? N2 C3 N3 C2 -63.4(3) . . . . ? N2 C3 N3 C19 167.1(3) . . . . ? C20 C19 N3 C2 57.7(4) . . . . ? C21 C19 N3 C2 173.9(3) . . . . ? C22 C19 N3 C2 -63.1(4) . . . . ? C20 C19 N3 C3 -177.2(3) . . . . ? C21 C19 N3 C3 -60.9(4) . . . . ? C22 C19 N3 C3 62.1(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.54 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.277 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.041 # Attachment 'md2007m.cif' data_md2007m _database_code_depnum_ccdc_archive 'CCDC 684400' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H28 N4 O4, C2 H6 O S' _chemical_formula_sum 'C34 H34 N4 O5 S' _chemical_formula_weight 610.71 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' S S 0.1246 0.1234 '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 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.4680(6) _cell_length_b 23.0549(15) _cell_length_c 13.3023(9) _cell_angle_alpha 90.00 _cell_angle_beta 92.765(2) _cell_angle_gamma 90.00 _cell_volume 2900.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 2019 _cell_measurement_theta_min 3.062 _cell_measurement_theta_max 23.592 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 0.163 _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 150(1) _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 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 21351 _diffrn_reflns_av_R_equivalents 0.0801 _diffrn_reflns_av_sigmaI/netI 0.0665 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 22.54 _reflns_number_total 3813 _reflns_number_gt 2456 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.625 (Bruker, 1998)' _computing_cell_refinement 'SAINT+ NT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT+ NT V6.22' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V6.1 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V6.1' _refine_special_details ; 023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 22.54 Deg. 027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 22.54 Deg. RESPONSE: No high-angle diffration observed due to the combined effects of crystal size and solvent disorder. 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^)+(0.0951P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3813 _refine_ls_number_parameters 413 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1044 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.1907 _refine_ls_wR_factor_gt 0.1722 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.6570(5) 0.5149(2) 0.8827(3) 0.0291(11) Uani 1 1 d . . . C2 C 0.6391(5) 0.62122(18) 0.8722(3) 0.0347(12) Uani 1 1 d . . . H2A H 0.7434 0.6194 0.8814 0.042 Uiso 1 1 calc R . . H2B H 0.6049 0.6486 0.9230 0.042 Uiso 1 1 calc R . . C3 C 0.6017(4) 0.64517(18) 0.7693(3) 0.0289(11) Uani 1 1 d . . . C4 C 0.6027(4) 0.70470(19) 0.7536(3) 0.0315(11) Uani 1 1 d . . . H4A H 0.6297 0.7296 0.8081 0.038 Uiso 1 1 calc R . . C5 C 0.5655(4) 0.72846(18) 0.6613(3) 0.0320(11) Uani 1 1 d . . . H5 H 0.5663 0.7694 0.6530 0.038 Uiso 1 1 calc R . . C6 C 0.5266(4) 0.69296(18) 0.5798(3) 0.0279(11) Uani 1 1 d . . . C7 C 0.5284(4) 0.63309(18) 0.5947(3) 0.0284(11) Uani 1 1 d . . . H7 H 0.5050 0.6080 0.5398 0.034 Uiso 1 1 calc R . . C8 C 0.5639(4) 0.60970(18) 0.6889(3) 0.0318(11) Uani 1 1 d . . . H8 H 0.5621 0.5688 0.6980 0.038 Uiso 1 1 calc R . . C9 C 0.4702(4) 0.7199(2) 0.4851(3) 0.0310(11) Uani 1 1 d . . . C10 C 0.4439(4) 0.68364(18) 0.3925(3) 0.0307(11) Uani 1 1 d . . . C11 C 0.3196(5) 0.69301(18) 0.3352(3) 0.0311(11) Uani 1 1 d . . . H11 H 0.2537 0.7210 0.3565 0.037 Uiso 1 1 calc R . . C12 C 0.2906(5) 0.66236(18) 0.2482(3) 0.0320(11) Uani 1 1 d . . . H12 H 0.2029 0.6682 0.2119 0.038 Uiso 1 1 calc R . . C13 C 0.3867(5) 0.62310(19) 0.2122(3) 0.0310(11) Uani 1 1 d . . . C14 C 0.5132(4) 0.61422(18) 0.2689(3) 0.0287(11) Uani 1 1 d . . . H14 H 0.5808 0.5875 0.2458 0.034 Uiso 1 1 calc R . . C15 C 0.5413(5) 0.64355(18) 0.3577(3) 0.0311(11) Uani 1 1 d . . . H15 H 0.6273 0.6366 0.3956 0.037 Uiso 1 1 calc R . . C16 C 0.3567(5) 0.59161(19) 0.1143(3) 0.0401(12) Uani 1 1 d . . . H16A H 0.2529 0.5885 0.1027 0.048 Uiso 1 1 calc R . . H16B H 0.3926 0.6155 0.0592 0.048 Uiso 1 1 calc R . . N1 N 0.5835(4) 0.46556(17) 0.8925(3) 0.0421(11) Uani 1 1 d . . . H1 H 0.4930 0.4684 0.9037 0.051 Uiso 1 1 calc R . . N2 N 0.5819(4) 0.56413(17) 0.8918(3) 0.0416(10) Uani 1 1 d . . . H2 H 0.4942 0.5615 0.9104 0.050 Uiso 1 1 calc R . . O1 O 0.7872(4) 0.51503(14) 0.8714(2) 0.0442(9) Uani 1 1 d . . . O2 O 0.4383(4) 0.77161(13) 0.4827(2) 0.0455(9) Uani 1 1 d . . . C17 C 0.1568(5) 0.5105(2) 0.8823(3) 0.0297(11) Uani 1 1 d . . . C18 C 0.1339(5) 0.40475(19) 0.8929(3) 0.0349(12) Uani 1 1 d . . . H18A H 0.0908 0.3818 0.9463 0.042 Uiso 1 1 calc R . . H18B H 0.2370 0.4064 0.9089 0.042 Uiso 1 1 calc R . . C19 C 0.1090(4) 0.37357(18) 0.7943(3) 0.0287(11) Uani 1 1 d . . . C20 C 0.1187(4) 0.31332(19) 0.7906(3) 0.0335(12) Uani 1 1 d . . . H20 H 0.1435 0.2924 0.8504 0.040 Uiso 1 1 calc R . . C21 C 0.0931(4) 0.28363(18) 0.7019(3) 0.0313(11) Uani 1 1 d . . . H21 H 0.1005 0.2425 0.7014 0.038 Uiso 1 1 calc R . . C22 C 0.0567(4) 0.31257(17) 0.6135(3) 0.0277(11) Uani 1 1 d . . . C23 C 0.0463(4) 0.37257(18) 0.6167(3) 0.0279(11) Uani 1 1 d . . . H23 H 0.0210 0.3933 0.5568 0.033 Uiso 1 1 calc R . . C24 C 0.0721(4) 0.40253(18) 0.7054(3) 0.0283(11) Uani 1 1 d . . . H24 H 0.0645 0.4436 0.7057 0.034 Uiso 1 1 calc R . . C25 C 0.0183(5) 0.2784(2) 0.5216(3) 0.0345(12) Uani 1 1 d . . . C26 C -0.0228(5) 0.30869(18) 0.4250(3) 0.0309(11) Uani 1 1 d . . . C27 C -0.1496(5) 0.29319(18) 0.3744(3) 0.0336(11) Uani 1 1 d . . . H27 H -0.2085 0.2646 0.4023 0.040 Uiso 1 1 calc R . . C28 C -0.1899(5) 0.31906(18) 0.2842(3) 0.0342(12) Uani 1 1 d . . . H28 H -0.2782 0.3090 0.2519 0.041 Uiso 1 1 calc R . . C29 C -0.1045(5) 0.35954(18) 0.2395(3) 0.0297(11) Uani 1 1 d . . . C30 C 0.0228(5) 0.37471(19) 0.2890(3) 0.0309(11) Uani 1 1 d . . . H30 H 0.0829 0.4023 0.2597 0.037 Uiso 1 1 calc R . . C31 C 0.0621(5) 0.34990(18) 0.3805(3) 0.0313(11) Uani 1 1 d . . . H31 H 0.1488 0.3611 0.4139 0.038 Uiso 1 1 calc R . . C32 C -0.1506(5) 0.38367(19) 0.1384(3) 0.0363(12) Uani 1 1 d . . . H32A H -0.1273 0.3551 0.0862 0.044 Uiso 1 1 calc R . . H32B H -0.2547 0.3882 0.1357 0.044 Uiso 1 1 calc R . . N3 N 0.0878(4) 0.56086(17) 0.8870(3) 0.0446(11) Uani 1 1 d . . . H3 H 0.0002 0.5605 0.9063 0.054 Uiso 1 1 calc R . . N4 N 0.0786(4) 0.46255(17) 0.8953(3) 0.0411(10) Uani 1 1 d . . . H4 H -0.0118 0.4670 0.9060 0.049 Uiso 1 1 calc R . . O3 O 0.2875(4) 0.50714(13) 0.8711(2) 0.0421(9) Uani 1 1 d . . . O4 O 0.0117(4) 0.22554(14) 0.5252(2) 0.0545(11) Uani 1 1 d . . . S1 S 0.2966(3) 0.48871(11) 0.51230(19) 0.0351(7) Uani 0.50 1 d P A 1 C33 C 0.2372(15) 0.5397(6) 0.5981(9) 0.040(4) Uiso 0.50 1 d P A 1 H33A H 0.2785 0.5311 0.6654 0.060 Uiso 0.50 1 calc PR A 1 H33B H 0.1339 0.5379 0.5991 0.060 Uiso 0.50 1 calc PR A 1 H33C H 0.2660 0.5786 0.5778 0.060 Uiso 0.50 1 calc PR A 1 C34 C 0.2261(17) 0.5229(6) 0.4010(11) 0.052(5) Uiso 0.50 1 d P A 1 H34A H 0.2628 0.5626 0.3974 0.078 Uiso 0.50 1 calc PR A 1 H34B H 0.1227 0.5240 0.4022 0.078 Uiso 0.50 1 calc PR A 1 H34C H 0.2539 0.5010 0.3420 0.078 Uiso 0.50 1 calc PR A 1 O5 O 0.4550(6) 0.4965(3) 0.5119(7) 0.048(2) Uani 0.50 1 d P . 1 S2 S 0.2029(3) 0.48825(11) 0.49052(19) 0.0372(7) Uani 0.50 1 d P B 2 C35 C 0.2719(16) 0.5268(6) 0.5989(10) 0.053(5) Uiso 0.50 1 d P B 2 H35A H 0.2379 0.5670 0.5961 0.080 Uiso 0.50 1 calc PR B 2 H35B H 0.3754 0.5265 0.5999 0.080 Uiso 0.50 1 calc PR B 2 H35C H 0.2400 0.5081 0.6599 0.080 Uiso 0.50 1 calc PR B 2 C36 C 0.2585(15) 0.5334(6) 0.3955(9) 0.037(4) Uiso 0.50 1 d P B 2 H36A H 0.2013 0.5260 0.3335 0.055 Uiso 0.50 1 calc PR B 2 H36B H 0.3582 0.5257 0.3839 0.055 Uiso 0.50 1 calc PR B 2 H36C H 0.2475 0.5740 0.4156 0.055 Uiso 0.50 1 calc PR B 2 O6 O 0.0456(5) 0.4961(3) 0.4909(7) 0.050(2) Uani 0.50 1 d P . 2 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 0.026(3) 0.041(3) 0.021(2) -0.001(2) 0.000(2) 0.000(3) C2 0.038(3) 0.032(3) 0.033(3) -0.005(2) -0.006(2) 0.003(2) C3 0.022(3) 0.029(3) 0.036(3) -0.008(2) 0.002(2) 0.000(2) C4 0.029(3) 0.030(3) 0.035(3) -0.011(2) 0.000(2) 0.000(2) C5 0.037(3) 0.018(2) 0.042(3) -0.004(2) 0.005(2) -0.001(2) C6 0.024(3) 0.024(3) 0.036(3) 0.000(2) 0.006(2) -0.006(2) C7 0.028(3) 0.026(3) 0.032(3) -0.005(2) 0.000(2) -0.003(2) C8 0.036(3) 0.022(2) 0.037(3) -0.002(2) -0.005(2) 0.001(2) C9 0.027(3) 0.030(3) 0.037(3) -0.002(2) 0.008(2) -0.006(2) C10 0.027(3) 0.032(3) 0.033(3) 0.008(2) 0.004(2) 0.002(2) C11 0.029(3) 0.024(3) 0.040(3) 0.009(2) 0.005(2) 0.005(2) C12 0.022(3) 0.031(3) 0.042(3) 0.015(2) -0.003(2) 0.001(2) C13 0.031(3) 0.028(3) 0.033(3) 0.010(2) -0.002(2) -0.002(2) C14 0.025(3) 0.028(2) 0.033(3) 0.004(2) 0.000(2) 0.000(2) C15 0.031(3) 0.033(3) 0.029(3) 0.006(2) -0.003(2) -0.003(2) C16 0.044(3) 0.036(3) 0.040(3) 0.008(2) -0.009(2) 0.002(2) N1 0.034(2) 0.046(3) 0.046(3) -0.001(2) -0.0017(19) 0.000(2) N2 0.038(3) 0.045(3) 0.042(2) 0.0019(19) 0.0010(19) 0.007(2) O1 0.033(2) 0.051(2) 0.049(2) 0.0009(17) 0.0006(16) 0.0014(17) O2 0.065(2) 0.0235(19) 0.048(2) 0.0054(15) 0.0078(17) 0.0066(17) C17 0.030(3) 0.036(3) 0.023(2) -0.002(2) -0.001(2) -0.005(3) C18 0.037(3) 0.033(3) 0.033(3) 0.008(2) -0.008(2) -0.006(2) C19 0.025(3) 0.028(3) 0.033(3) 0.006(2) 0.000(2) -0.003(2) C20 0.029(3) 0.033(3) 0.039(3) 0.014(2) -0.003(2) 0.001(2) C21 0.033(3) 0.020(2) 0.040(3) 0.003(2) -0.001(2) 0.000(2) C22 0.024(3) 0.024(3) 0.035(3) 0.000(2) 0.005(2) -0.002(2) C23 0.025(3) 0.030(3) 0.029(2) 0.004(2) -0.0028(19) 0.000(2) C24 0.031(3) 0.024(2) 0.029(3) 0.003(2) -0.004(2) 0.002(2) C25 0.035(3) 0.028(3) 0.042(3) -0.001(2) 0.012(2) -0.001(2) C26 0.039(3) 0.024(3) 0.030(3) -0.004(2) 0.007(2) -0.003(2) C27 0.036(3) 0.023(3) 0.043(3) -0.005(2) 0.011(2) -0.006(2) C28 0.028(3) 0.031(3) 0.043(3) -0.011(2) -0.004(2) -0.002(2) C29 0.028(3) 0.025(3) 0.036(3) -0.008(2) 0.001(2) 0.004(2) C30 0.032(3) 0.032(3) 0.028(3) 0.000(2) 0.001(2) -0.001(2) C31 0.027(3) 0.034(3) 0.033(3) -0.006(2) -0.001(2) -0.004(2) C32 0.039(3) 0.030(3) 0.038(3) -0.004(2) -0.012(2) -0.002(2) N3 0.042(3) 0.046(3) 0.046(3) 0.000(2) -0.001(2) 0.006(2) N4 0.035(2) 0.048(3) 0.039(2) -0.0016(19) -0.0008(19) 0.002(2) O3 0.033(2) 0.044(2) 0.049(2) 0.0007(16) -0.0020(16) 0.0012(16) O4 0.094(3) 0.028(2) 0.042(2) 0.0004(16) 0.0088(19) -0.0064(19) S1 0.0330(19) 0.0277(14) 0.0438(16) -0.0002(11) -0.0057(13) 0.0020(14) O5 0.028(7) 0.039(4) 0.076(6) -0.016(4) -0.003(5) -0.003(5) S2 0.038(2) 0.0304(15) 0.0419(16) 0.0041(11) -0.0064(14) -0.0014(14) O6 0.013(5) 0.055(4) 0.082(5) 0.018(4) 0.001(5) -0.007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.250(5) . ? C1 N1 1.343(6) . ? C1 N2 1.348(6) . ? C2 N2 1.452(5) . ? C2 C3 1.503(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.379(6) . ? C3 C4 1.388(6) . ? C4 C5 1.375(6) . ? C4 H4A 0.9500 . ? C5 C6 1.394(6) . ? C5 H5 0.9500 . ? C6 C7 1.394(6) . ? C6 C9 1.482(6) . ? C7 C8 1.390(6) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 O2 1.229(5) . ? C9 C10 1.499(6) . ? C10 C11 1.388(6) . ? C10 C15 1.401(6) . ? C11 C12 1.373(6) . ? C11 H11 0.9500 . ? C12 C13 1.385(6) . ? C12 H12 0.9500 . ? C13 C14 1.400(6) . ? C13 C16 1.506(6) . ? C14 C15 1.375(6) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 N1 1.439(6) 3_666 ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? N1 C16 1.439(6) 3_666 ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? C17 O3 1.256(5) . ? C17 N3 1.334(6) . ? C17 N4 1.347(6) . ? C18 N4 1.433(5) . ? C18 C19 1.504(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.388(5) . ? C19 C20 1.393(6) . ? C20 C21 1.376(6) . ? C20 H20 0.9500 . ? C21 C22 1.381(6) . ? C21 H21 0.9500 . ? C22 C23 1.388(5) . ? C22 C25 1.484(6) . ? C23 C24 1.379(5) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 O4 1.222(5) . ? C25 C26 1.497(6) . ? C26 C27 1.394(6) . ? C26 C31 1.395(6) . ? C27 C28 1.378(6) . ? C27 H27 0.9500 . ? C28 C29 1.388(6) . ? C28 H28 0.9500 . ? C29 C30 1.390(6) . ? C29 C32 1.501(6) . ? C30 C31 1.380(6) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 N3 1.456(5) 3_566 ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? N3 C32 1.456(5) 3_566 ? N3 H3 0.8800 . ? N4 H4 0.8800 . ? S1 O5 1.511(6) . ? S1 C33 1.750(12) . ? S1 C34 1.779(14) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? O5 O5 0.937(11) 3_666 ? S2 O6 1.500(6) . ? S2 C36 1.739(13) . ? S2 C35 1.790(14) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? O6 O6 0.927(11) 3_566 ? 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 C1 N1 122.2(4) . . ? O1 C1 N2 122.5(4) . . ? N1 C1 N2 115.3(4) . . ? N2 C2 C3 115.0(3) . . ? N2 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? N2 C2 H2B 108.5 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C8 C3 C4 118.2(4) . . ? C8 C3 C2 122.0(4) . . ? C4 C3 C2 119.8(4) . . ? C5 C4 C3 121.6(4) . . ? C5 C4 H4A 119.2 . . ? C3 C4 H4A 119.2 . . ? C4 C5 C6 120.5(4) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C7 118.0(4) . . ? C5 C6 C9 119.1(4) . . ? C7 C6 C9 122.5(4) . . ? C8 C7 C6 120.9(4) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C3 C8 C7 120.7(4) . . ? C3 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? O2 C9 C6 120.4(4) . . ? O2 C9 C10 119.3(4) . . ? C6 C9 C10 120.2(4) . . ? C11 C10 C15 118.4(4) . . ? C11 C10 C9 117.8(4) . . ? C15 C10 C9 123.6(4) . . ? C12 C11 C10 120.8(4) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 121.4(4) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C12 C13 C14 117.9(4) . . ? C12 C13 C16 121.0(4) . . ? C14 C13 C16 121.1(4) . . ? C15 C14 C13 121.1(4) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C10 120.3(4) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? N1 C16 C13 115.9(4) 3_666 . ? N1 C16 H16A 108.3 3_666 . ? C13 C16 H16A 108.3 . . ? N1 C16 H16B 108.3 3_666 . ? C13 C16 H16B 108.3 . . ? H16A C16 H16B 107.4 . . ? C1 N1 C16 124.2(4) . 3_666 ? C1 N1 H1 117.9 . . ? C16 N1 H1 117.9 3_666 . ? C1 N2 C2 123.0(4) . . ? C1 N2 H2 118.5 . . ? C2 N2 H2 118.5 . . ? O3 C17 N3 123.2(4) . . ? O3 C17 N4 121.0(4) . . ? N3 C17 N4 115.8(4) . . ? N4 C18 C19 115.0(3) . . ? N4 C18 H18A 108.5 . . ? C19 C18 H18A 108.5 . . ? N4 C18 H18B 108.5 . . ? C19 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C24 C19 C20 117.6(4) . . ? C24 C19 C18 122.4(4) . . ? C20 C19 C18 120.0(4) . . ? C21 C20 C19 121.1(4) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C20 C21 C22 121.1(4) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C21 C22 C23 118.1(4) . . ? C21 C22 C25 119.1(4) . . ? C23 C22 C25 122.6(4) . . ? C24 C23 C22 121.0(4) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C19 121.0(4) . . ? C23 C24 H24 119.5 . . ? C19 C24 H24 119.5 . . ? O4 C25 C22 120.5(4) . . ? O4 C25 C26 119.1(4) . . ? C22 C25 C26 120.2(4) . . ? C27 C26 C31 118.1(4) . . ? C27 C26 C25 118.5(4) . . ? C31 C26 C25 123.4(4) . . ? C28 C27 C26 120.4(4) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C29 121.5(4) . . ? C27 C28 H28 119.3 . . ? C29 C28 H28 119.3 . . ? C28 C29 C30 118.4(4) . . ? C28 C29 C32 118.9(4) . . ? C30 C29 C32 122.7(4) . . ? C31 C30 C29 120.3(4) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C30 C31 C26 121.3(4) . . ? C30 C31 H31 119.4 . . ? C26 C31 H31 119.4 . . ? N3 C32 C29 115.4(3) 3_566 . ? N3 C32 H32A 108.4 3_566 . ? C29 C32 H32A 108.4 . . ? N3 C32 H32B 108.4 3_566 . ? C29 C32 H32B 108.4 . . ? H32A C32 H32B 107.5 . . ? C17 N3 C32 123.2(4) . 3_566 ? C17 N3 H3 118.4 . . ? C32 N3 H3 118.4 3_566 . ? C17 N4 C18 123.9(4) . . ? C17 N4 H4 118.1 . . ? C18 N4 H4 118.1 . . ? O5 S1 C33 105.8(6) . . ? O5 S1 C34 106.1(6) . . ? C33 S1 C34 97.2(7) . . ? S1 C33 H33A 109.5 . . ? S1 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? S1 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? S1 C34 H34A 109.5 . . ? S1 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? S1 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O5 O5 S1 160.0(14) 3_666 . ? O6 S2 C36 105.4(6) . . ? O6 S2 C35 105.2(6) . . ? C36 S2 C35 100.2(7) . . ? S2 C35 H35A 109.5 . . ? S2 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? S2 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? S2 C36 H36A 109.5 . . ? S2 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? S2 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O6 O6 S2 164.3(14) 3_566 . ? 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 N2 C2 C3 C8 -23.0(6) . . . . ? N2 C2 C3 C4 156.0(4) . . . . ? C8 C3 C4 C5 0.8(7) . . . . ? C2 C3 C4 C5 -178.2(4) . . . . ? C3 C4 C5 C6 -0.6(7) . . . . ? C4 C5 C6 C7 -0.8(6) . . . . ? C4 C5 C6 C9 172.5(4) . . . . ? C5 C6 C7 C8 1.9(6) . . . . ? C9 C6 C7 C8 -171.1(4) . . . . ? C4 C3 C8 C7 0.3(6) . . . . ? C2 C3 C8 C7 179.3(4) . . . . ? C6 C7 C8 C3 -1.7(7) . . . . ? C5 C6 C9 O2 -10.8(6) . . . . ? C7 C6 C9 O2 162.1(4) . . . . ? C5 C6 C9 C10 172.7(4) . . . . ? C7 C6 C9 C10 -14.4(6) . . . . ? O2 C9 C10 C11 -39.6(6) . . . . ? C6 C9 C10 C11 137.0(4) . . . . ? O2 C9 C10 C15 136.4(5) . . . . ? C6 C9 C10 C15 -47.1(6) . . . . ? C15 C10 C11 C12 2.1(6) . . . . ? C9 C10 C11 C12 178.3(4) . . . . ? C10 C11 C12 C13 -3.0(6) . . . . ? C11 C12 C13 C14 1.9(6) . . . . ? C11 C12 C13 C16 -177.3(4) . . . . ? C12 C13 C14 C15 0.0(6) . . . . ? C16 C13 C14 C15 179.2(4) . . . . ? C13 C14 C15 C10 -0.8(6) . . . . ? C11 C10 C15 C14 -0.3(6) . . . . ? C9 C10 C15 C14 -176.2(4) . . . . ? C12 C13 C16 N1 -149.2(4) . . . 3_666 ? C14 C13 C16 N1 31.7(6) . . . 3_666 ? O1 C1 N1 C16 -3.4(6) . . . 3_666 ? N2 C1 N1 C16 -179.8(4) . . . 3_666 ? O1 C1 N2 C2 10.8(6) . . . . ? N1 C1 N2 C2 -172.8(4) . . . . ? C3 C2 N2 C1 97.6(5) . . . . ? N4 C18 C19 C24 17.2(6) . . . . ? N4 C18 C19 C20 -160.9(4) . . . . ? C24 C19 C20 C21 0.2(6) . . . . ? C18 C19 C20 C21 178.4(4) . . . . ? C19 C20 C21 C22 -0.1(7) . . . . ? C20 C21 C22 C23 -0.2(6) . . . . ? C20 C21 C22 C25 -174.9(4) . . . . ? C21 C22 C23 C24 0.3(6) . . . . ? C25 C22 C23 C24 174.8(4) . . . . ? C22 C23 C24 C19 -0.1(6) . . . . ? C20 C19 C24 C23 -0.1(6) . . . . ? C18 C19 C24 C23 -178.3(4) . . . . ? C21 C22 C25 O4 3.8(7) . . . . ? C23 C22 C25 O4 -170.7(4) . . . . ? C21 C22 C25 C26 179.5(4) . . . . ? C23 C22 C25 C26 5.0(6) . . . . ? O4 C25 C26 C27 48.1(6) . . . . ? C22 C25 C26 C27 -127.7(4) . . . . ? O4 C25 C26 C31 -129.1(5) . . . . ? C22 C25 C26 C31 55.1(6) . . . . ? C31 C26 C27 C28 -1.3(6) . . . . ? C25 C26 C27 C28 -178.6(4) . . . . ? C26 C27 C28 C29 2.1(7) . . . . ? C27 C28 C29 C30 -1.4(6) . . . . ? C27 C28 C29 C32 176.6(4) . . . . ? C28 C29 C30 C31 -0.1(6) . . . . ? C32 C29 C30 C31 -178.0(4) . . . . ? C29 C30 C31 C26 0.9(6) . . . . ? C27 C26 C31 C30 -0.2(6) . . . . ? C25 C26 C31 C30 177.0(4) . . . . ? C28 C29 C32 N3 158.4(4) . . . 3_566 ? C30 C29 C32 N3 -23.7(6) . . . 3_566 ? O3 C17 N3 C32 11.4(6) . . . 3_566 ? N4 C17 N3 C32 -171.7(4) . . . 3_566 ? O3 C17 N4 C18 -3.1(6) . . . . ? N3 C17 N4 C18 180.0(4) . . . . ? C19 C18 N4 C17 -98.3(5) . . . . ? 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 N1 H1 O3 0.88 2.17 2.963(5) 150 . N2 H2 O3 0.88 2.36 3.082(5) 139 . N3 H3 O1 0.88 2.30 3.034(5) 141 1_455 N4 H4 O1 0.88 2.23 3.015(5) 148 1_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.54 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.610 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.060