# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_HEt2L _audit_creation_date 2012-11-20T09:39:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common ? _chemical_formula_moiety 'C20 H20 N2 O8 S' _chemical_formula_sum 'C20 H20 N2 O8 S' _chemical_formula_weight 448.44 _chemical_compound_source ? #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _space_group_IT_number 2 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5660(3) _cell_length_b 11.5600(4) _cell_length_c 12.2620(4) _cell_angle_alpha 74.727(2) _cell_angle_beta 76.510(2) _cell_angle_gamma 78.804(2) _cell_volume 995.93(6) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 13649 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.103 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'fine-focus sealed tube' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.0615877 _diffrn_orient_matrix_ub_12 0.068879 _diffrn_orient_matrix_ub_13 -0.0525463 _diffrn_orient_matrix_ub_21 -0.0246207 _diffrn_orient_matrix_ub_22 0.0418411 _diffrn_orient_matrix_ub_23 0.064875 _diffrn_orient_matrix_ub_31 0.1202161 _diffrn_orient_matrix_ub_32 -0.041355 _diffrn_orient_matrix_ub_33 0.0212695 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_unetI/netI 0.0399 _diffrn_reflns_number 17023 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 3488 _reflns_number_gt 2832 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0372P)^2^+0.3271P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0081(17) _refine_ls_number_reflns 3488 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.034 _refine_ls_wR_factor_ref 0.083 _refine_ls_wR_factor_gt 0.0765 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.02 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.216 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.046 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.5551(2) 0.22310(17) 0.12353(15) 0.0212(4) Uani 1 1 d . . . C2 C 0.6165(2) 0.10214(16) 0.16677(15) 0.0226(4) Uani 1 1 d . . . H2 H 0.6407 0.046 0.119 0.027 Uiso 1 1 calc R . . C3 C 0.6427(3) 0.06306(17) 0.28003(15) 0.0226(4) Uani 1 1 d . . . H3 H 0.6847 -0.0197 0.3101 0.027 Uiso 1 1 calc R . . C4 C 0.6067(2) 0.14661(16) 0.34895(14) 0.0201(4) Uani 1 1 d . . . C5 C 0.5372(2) 0.26719(16) 0.30659(15) 0.0221(4) Uani 1 1 d . . . H5 H 0.507 0.3226 0.3554 0.027 Uiso 1 1 calc R . . C6 C 0.5123(3) 0.30623(17) 0.19366(15) 0.0223(4) Uani 1 1 d . . . H6 H 0.4666 0.3884 0.1642 0.027 Uiso 1 1 calc R . . C7 C 0.7517(3) 0.01826(16) 0.50941(15) 0.0224(4) Uani 1 1 d . . . C8 C 0.7638(2) 0.02354(16) 0.63148(15) 0.0224(4) Uani 1 1 d . . . C9 C 0.8653(3) -0.08147(17) 0.80258(15) 0.0266(4) Uani 1 1 d . . . H9A H 0.7458 -0.0548 0.849 0.032 Uiso 1 1 calc R . . H9B H 0.952 -0.0255 0.7978 0.032 Uiso 1 1 calc R . . C10 C 0.9381(3) -0.20799(18) 0.85748(17) 0.0315(5) Uani 1 1 d . . . H10A H 0.8559(14) -0.2625(7) 0.8580(11) 0.047 Uiso 1 1 calc R . . H10B H 0.9474(18) -0.2119(3) 0.9356(10) 0.047 Uiso 1 1 calc R . . H10C H 1.0580(17) -0.2313(6) 0.8143(9) 0.047 Uiso 1 1 calc R . . C11 C 0.7648(2) 0.30184(16) -0.09351(14) 0.0200(4) Uani 1 1 d . . . C12 C 0.8674(3) 0.23111(17) -0.16740(16) 0.0248(4) Uani 1 1 d . . . H12 H 0.8179 0.167 -0.1794 0.03 Uiso 1 1 calc R . . C13 C 1.0434(3) 0.25395(17) -0.22429(16) 0.0257(4) Uani 1 1 d . . . H13 H 1.1143 0.2063 -0.276 0.031 Uiso 1 1 calc R . . C14 C 1.1141(2) 0.34716(16) -0.20460(15) 0.0211(4) Uani 1 1 d . . . C15 C 1.0089(3) 0.41833(17) -0.12982(15) 0.0232(4) Uani 1 1 d . . . H15 H 1.0584 0.4819 -0.1168 0.028 Uiso 1 1 calc R . . C16 C 0.8334(3) 0.39672(16) -0.07487(15) 0.0226(4) Uani 1 1 d . . . H16 H 0.7606 0.4458 -0.0251 0.027 Uiso 1 1 calc R . . C17 C 1.3988(3) 0.34494(16) -0.35356(15) 0.0230(4) Uani 1 1 d . . . C18 C 1.5830(3) 0.39303(16) -0.38164(15) 0.0232(4) Uani 1 1 d . . . C19 C 1.8697(3) 0.40071(18) -0.50789(17) 0.0284(4) Uani 1 1 d . . . H19A H 1.9308 0.3692 -0.4406 0.034 Uiso 1 1 calc R . . H19B H 1.8644 0.4899 -0.53 0.034 Uiso 1 1 calc R . . C20 C 1.9748(3) 0.34664(19) -0.60597(19) 0.0369(5) Uani 1 1 d . . . H20A H 1.9900(18) 0.2572(11) -0.5806(5) 0.055 Uiso 1 1 calc R . . H20B H 2.0970(17) 0.3740(11) -0.6321(9) 0.055 Uiso 1 1 calc R . . H20C H 1.9069(13) 0.3729(11) -0.6703(10) 0.055 Uiso 1 1 calc R . . O1 O 0.50178(18) 0.17304(12) -0.06082(11) 0.0273(3) Uani 1 1 d . . . O2 O 0.41886(17) 0.38570(11) -0.03912(10) 0.0242(3) Uani 1 1 d . . . O3 O 0.83814(19) -0.06253(12) 0.46394(11) 0.0300(3) Uani 1 1 d . . . O4 O 0.70657(19) 0.11291(12) 0.66920(11) 0.0294(3) Uani 1 1 d . . . O5 O 0.84262(18) -0.08051(11) 0.68699(10) 0.0250(3) Uani 1 1 d . . . O6 O 1.35862(18) 0.28964(13) -0.41409(11) 0.0315(3) Uani 1 1 d . . . O7 O 1.62465(19) 0.44787(12) -0.32203(11) 0.0297(3) Uani 1 1 d . . . O8 O 1.68437(17) 0.36823(12) -0.47859(10) 0.0259(3) Uani 1 1 d . . . N1 N 0.6377(2) 0.11489(14) 0.46287(13) 0.0221(4) Uani 1 1 d . . . N2 N 1.2927(2) 0.37510(14) -0.25755(13) 0.0232(4) Uani 1 1 d . . . S1 S 0.54038(6) 0.27196(4) -0.02347(4) 0.02129(14) Uani 1 1 d . . . H11 H 1.341(3) 0.4110(19) -0.2237(17) 0.027(6) Uiso 1 1 d . . . H22 H 0.589(3) 0.170(2) 0.501(2) 0.040(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 C1 0.0197(10) 0.0274(10) 0.0170(9) -0.0061(8) -0.0034(7) -0.0034(8) C2 0.0239(10) 0.0240(10) 0.0219(9) -0.0098(8) -0.0036(8) -0.0033(8) C3 0.0247(10) 0.0210(9) 0.0217(9) -0.0057(7) -0.0043(8) -0.0016(8) C4 0.0199(9) 0.0242(10) 0.0162(9) -0.0042(7) -0.0029(7) -0.0044(8) C5 0.0240(10) 0.0232(10) 0.0210(9) -0.0100(7) -0.0040(8) -0.0013(8) C6 0.0232(10) 0.0222(9) 0.0214(9) -0.0058(7) -0.0046(8) -0.0015(8) C7 0.0251(10) 0.0227(10) 0.0196(9) -0.0041(8) -0.0036(8) -0.0060(8) C8 0.0229(10) 0.0232(10) 0.0213(9) -0.0045(8) -0.0040(8) -0.0053(8) C9 0.0304(11) 0.0314(11) 0.0196(9) -0.0064(8) -0.0076(8) -0.0036(9) C10 0.0311(11) 0.0342(11) 0.0258(10) 0.0003(8) -0.0087(9) -0.0022(9) C11 0.0209(10) 0.0227(9) 0.0155(9) -0.0036(7) -0.0051(7) -0.0005(8) C12 0.0291(11) 0.0231(10) 0.0240(10) -0.0091(8) -0.0050(8) -0.0031(8) C13 0.0274(11) 0.0249(10) 0.0249(10) -0.0122(8) -0.0021(8) 0.0013(8) C14 0.0225(10) 0.0232(10) 0.0159(9) -0.0023(7) -0.0053(7) 0.0000(8) C15 0.0266(10) 0.0237(10) 0.0213(9) -0.0080(8) -0.0051(8) -0.0036(8) C16 0.0272(10) 0.0223(9) 0.0178(9) -0.0078(7) -0.0040(8) 0.0014(8) C17 0.0240(10) 0.0242(10) 0.0194(9) -0.0052(8) -0.0052(8) 0.0014(8) C18 0.0237(10) 0.0227(10) 0.0212(9) -0.0039(8) -0.0055(8) 0.0008(8) C19 0.0217(10) 0.0309(11) 0.0307(11) -0.0023(8) -0.0037(8) -0.0076(8) C20 0.0308(12) 0.0336(12) 0.0397(12) -0.0078(10) 0.0045(10) -0.0035(10) O1 0.0320(8) 0.0292(7) 0.0249(7) -0.0107(6) -0.0064(6) -0.0073(6) O2 0.0231(7) 0.0276(7) 0.0208(6) -0.0067(5) -0.0058(5) 0.0026(6) O3 0.0351(8) 0.0292(8) 0.0260(7) -0.0103(6) -0.0086(6) 0.0038(6) O4 0.0396(8) 0.0261(7) 0.0249(7) -0.0091(6) -0.0103(6) -0.0007(6) O5 0.0313(8) 0.0244(7) 0.0192(6) -0.0040(5) -0.0085(6) -0.0008(6) O6 0.0278(8) 0.0435(9) 0.0280(7) -0.0186(7) -0.0011(6) -0.0075(6) O7 0.0317(8) 0.0338(8) 0.0276(7) -0.0126(6) -0.0045(6) -0.0076(6) O8 0.0236(7) 0.0309(7) 0.0231(7) -0.0092(6) 0.0004(6) -0.0058(6) N1 0.0283(9) 0.0210(8) 0.0175(8) -0.0067(7) -0.0054(7) 0.0000(7) N2 0.0231(9) 0.0272(9) 0.0220(8) -0.0100(7) -0.0048(7) -0.0035(7) S1 0.0216(3) 0.0256(3) 0.0175(2) -0.00678(18) -0.00450(18) -0.00171(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C2 1.387(3) . ? C1 C6 1.397(2) . ? C1 S1 1.7645(17) . ? C2 C3 1.391(3) . ? C2 H2 0.95 . ? C3 C4 1.393(2) . ? C3 H3 0.95 . ? C4 C5 1.397(3) . ? C4 N1 1.411(2) . ? C5 C6 1.384(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 O3 1.216(2) . ? C7 N1 1.355(2) . ? C7 C8 1.539(2) . ? C8 O4 1.205(2) . ? C8 O5 1.321(2) . ? C9 O5 1.464(2) . ? C9 C10 1.496(3) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 H10A 0.9653 . ? C10 H10B 0.9653 . ? C10 H10C 0.9653 . ? C11 C12 1.381(3) . ? C11 C16 1.390(3) . ? C11 S1 1.7692(18) . ? C12 C13 1.391(3) . ? C12 H12 0.95 . ? C13 C14 1.388(3) . ? C13 H13 0.95 . ? C14 C15 1.398(3) . ? C14 N2 1.415(2) . ? C15 C16 1.379(3) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C17 O6 1.218(2) . ? C17 N2 1.349(2) . ? C17 C18 1.532(3) . ? C18 O7 1.210(2) . ? C18 O8 1.324(2) . ? C19 O8 1.461(2) . ? C19 C20 1.492(3) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 H20A 0.9902 . ? C20 H20B 0.9902 . ? C20 H20C 0.9902 . ? O1 S1 1.4390(13) . ? O2 S1 1.4460(13) . ? N1 H22 0.87(2) . ? N2 H11 0.84(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 C2 C1 C6 120.82(16) . . ? C2 C1 S1 118.88(14) . . ? C6 C1 S1 120.25(14) . . ? C1 C2 C3 120.04(17) . . ? C1 C2 H2 120 . . ? C3 C2 H2 120 . . ? C2 C3 C4 119.27(17) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 120.44(16) . . ? C3 C4 N1 122.52(16) . . ? C5 C4 N1 117.04(16) . . ? C6 C5 C4 120.21(16) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 119.11(17) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? O3 C7 N1 126.90(17) . . ? O3 C7 C8 122.37(17) . . ? N1 C7 C8 110.72(15) . . ? O4 C8 O5 125.79(17) . . ? O4 C8 C7 122.70(17) . . ? O5 C8 C7 111.51(15) . . ? O5 C9 C10 107.98(15) . . ? O5 C9 H9A 110.1 . . ? C10 C9 H9A 110.1 . . ? O5 C9 H9B 110.1 . . ? C10 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 121.27(17) . . ? C12 C11 S1 119.01(14) . . ? C16 C11 S1 119.72(13) . . ? C11 C12 C13 119.91(17) . . ? C11 C12 H12 120 . . ? C13 C12 H12 120 . . ? C14 C13 C12 119.16(17) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 120.43(17) . . ? C13 C14 N2 122.73(16) . . ? C15 C14 N2 116.83(16) . . ? C16 C15 C14 120.30(17) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C11 118.90(16) . . ? C15 C16 H16 120.6 . . ? C11 C16 H16 120.6 . . ? O6 C17 N2 126.83(18) . . ? O6 C17 C18 122.32(16) . . ? N2 C17 C18 110.84(15) . . ? O7 C18 O8 126.05(17) . . ? O7 C18 C17 122.91(16) . . ? O8 C18 C17 111.03(15) . . ? O8 C19 C20 108.17(16) . . ? O8 C19 H19A 110.1 . . ? C20 C19 H19A 110.1 . . ? O8 C19 H19B 110.1 . . ? C20 C19 H19B 110.1 . . ? H19A C19 H19B 108.4 . . ? 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 . . ? C8 O5 C9 114.83(14) . . ? C18 O8 C19 115.38(14) . . ? C7 N1 C4 126.71(16) . . ? C7 N1 H22 119.0(15) . . ? C4 N1 H22 113.7(15) . . ? C17 N2 C14 127.53(16) . . ? C17 N2 H11 115.7(14) . . ? C14 N2 H11 116.7(14) . . ? O1 S1 O2 118.95(8) . . ? O1 S1 C1 108.71(8) . . ? O2 S1 C1 108.29(8) . . ? O1 S1 C11 108.31(8) . . ? O2 S1 C11 107.67(8) . . ? C1 S1 C11 103.88(8) . . ? 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 C6 C1 C2 C3 -2.4(3) . . . . ? S1 C1 C2 C3 175.14(14) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C2 C3 C4 C5 2.8(3) . . . . ? C2 C3 C4 N1 -177.11(16) . . . . ? C3 C4 C5 C6 -3.3(3) . . . . ? N1 C4 C5 C6 176.67(16) . . . . ? C4 C5 C6 C1 0.9(3) . . . . ? C2 C1 C6 C5 2.0(3) . . . . ? S1 C1 C6 C5 -175.53(14) . . . . ? O3 C7 C8 O4 166.08(18) . . . . ? N1 C7 C8 O4 -12.7(2) . . . . ? O3 C7 C8 O5 -14.2(2) . . . . ? N1 C7 C8 O5 167.05(15) . . . . ? C16 C11 C12 C13 0.3(3) . . . . ? S1 C11 C12 C13 179.30(14) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C12 C13 C14 C15 -0.9(3) . . . . ? C12 C13 C14 N2 179.00(17) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? N2 C14 C15 C16 -179.99(16) . . . . ? C14 C15 C16 C11 1.2(3) . . . . ? C12 C11 C16 C15 -1.3(3) . . . . ? S1 C11 C16 C15 179.73(13) . . . . ? O6 C17 C18 O7 -179.85(18) . . . . ? N2 C17 C18 O7 1.6(3) . . . . ? O6 C17 C18 O8 1.3(2) . . . . ? N2 C17 C18 O8 -177.25(15) . . . . ? O4 C8 O5 C9 -2.4(3) . . . . ? C7 C8 O5 C9 177.91(14) . . . . ? C10 C9 O5 C8 174.36(16) . . . . ? O7 C18 O8 C19 6.4(3) . . . . ? C17 C18 O8 C19 -174.76(14) . . . . ? C20 C19 O8 C18 169.70(16) . . . . ? O3 C7 N1 C4 -5.2(3) . . . . ? C8 C7 N1 C4 173.46(16) . . . . ? C3 C4 N1 C7 21.5(3) . . . . ? C5 C4 N1 C7 -158.43(17) . . . . ? O6 C17 N2 C14 1.6(3) . . . . ? C18 C17 N2 C14 179.99(16) . . . . ? C13 C14 N2 C17 20.0(3) . . . . ? C15 C14 N2 C17 -160.06(18) . . . . ? C2 C1 S1 O1 30.30(17) . . . . ? C6 C1 S1 O1 -152.14(14) . . . . ? C2 C1 S1 O2 160.85(14) . . . . ? C6 C1 S1 O2 -21.59(17) . . . . ? C2 C1 S1 C11 -84.88(16) . . . . ? C6 C1 S1 C11 92.68(16) . . . . ? C12 C11 S1 O1 -1.07(17) . . . . ? C16 C11 S1 O1 177.90(14) . . . . ? C12 C11 S1 O2 -130.91(15) . . . . ? C16 C11 S1 O2 48.07(16) . . . . ? C12 C11 S1 C1 114.38(15) . . . . ? C16 C11 S1 C1 -66.64(16) . . . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 949943' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_H4L _audit_update_record ; 2013-07-12 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 N2 O8 S, 2(H2 O)' _chemical_formula_sum 'C16 H16 N2 O10 S' _chemical_formula_weight 428.37 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 orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 10.4318(6) _cell_length_b 16.6580(10) _cell_length_c 10.1656(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1766.51(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1341 _cell_measurement_theta_min 4.1494 _cell_measurement_theta_max 29.3153 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76424 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4627 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1865 _reflns_number_gt 1046 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _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^)+(0.0335P)^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_number_reflns 1865 _refine_ls_number_parameters 149 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0750 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 0.803 _refine_ls_restrained_S_all 0.802 _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 O5 O 0.07420(15) 0.42377(9) 0.44339(13) 0.0494(4) Uani 1 1 d . . . O3 O -0.04617(16) 0.42154(9) 0.12377(14) 0.0546(5) Uani 1 1 d . . . C7 C -0.0355(2) 0.44296(14) 0.2381(2) 0.0383(6) Uani 1 1 d . . . C8 C 0.0639(2) 0.40518(13) 0.3296(2) 0.0371(5) Uani 1 1 d . . . O4 O 0.13258(15) 0.35105(9) 0.26867(12) 0.0488(4) Uani 1 1 d . . . H4 H 0.1847 0.3317 0.3200 0.073 Uiso 1 1 calc R . . O2W O 0.9983(2) 0.2500 0.0488(2) 0.0534(7) Uani 1 2 d SD . . O1W O 0.2464(2) 0.2500 0.4284(2) 0.0444(6) Uani 1 2 d SD . . H7 H 0.210(2) 0.2500 0.5011(17) 0.078(14) Uiso 1 2 d SD . . H8 H 0.3255(10) 0.2500 0.440(2) 0.055(11) Uiso 1 2 d SD . . H9 H 1.024(3) 0.2886(12) 0.095(2) 0.108(12) Uiso 1 1 d D . . S1 S -0.44445(7) 0.7500 0.07991(7) 0.0373(2) Uani 1 2 d S . . N1 N -0.10571(16) 0.49963(10) 0.29871(14) 0.0373(4) Uani 1 1 d . . . H1 H -0.0954 0.5040 0.3823 0.045 Uiso 1 1 calc R . . O2 O -0.56838(19) 0.7500 0.14255(18) 0.0470(6) Uani 1 2 d S . . O1 O -0.4368(2) 0.7500 -0.06144(16) 0.0437(6) Uani 1 2 d S . . C4 C -0.1943(2) 0.55264(12) 0.24029(17) 0.0314(5) Uani 1 1 d . . . C2 C -0.2638(2) 0.63319(14) 0.06072(18) 0.0377(5) Uani 1 1 d . . . H2 H -0.2561 0.6493 -0.0265 0.045 Uiso 1 1 calc R . . C1 C -0.35589(18) 0.66775(12) 0.13961(17) 0.0310(5) Uani 1 1 d . . . C3 C -0.1831(2) 0.57497(13) 0.10993(18) 0.0364(5) Uani 1 1 d . . . H3 H -0.1220 0.5510 0.0561 0.044 Uiso 1 1 calc R . . C5 C -0.28838(19) 0.58581(13) 0.31921(18) 0.0363(5) Uani 1 1 d . . . H5 H -0.2968 0.5692 0.4061 0.044 Uiso 1 1 calc R . . C6 C -0.3696(2) 0.64351(12) 0.26924(18) 0.0361(5) Uani 1 1 d . . . H6 H -0.4330 0.6659 0.3220 0.043 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 O5 0.0590(11) 0.0505(10) 0.0387(8) -0.0066(8) -0.0097(7) 0.0103(9) O3 0.0695(12) 0.0557(11) 0.0388(8) -0.0088(8) -0.0076(8) 0.0175(10) C7 0.0410(14) 0.0396(14) 0.0344(12) -0.0005(12) -0.0003(10) -0.0029(12) C8 0.0363(12) 0.0352(13) 0.0398(12) 0.0005(11) 0.0031(10) -0.0018(12) O4 0.0505(9) 0.0529(11) 0.0429(8) -0.0010(8) 0.0010(7) 0.0182(9) O2W 0.0448(14) 0.0591(18) 0.0565(15) 0.000 -0.0049(12) 0.000 O1W 0.0279(12) 0.0548(16) 0.0505(14) 0.000 0.0001(11) 0.000 S1 0.0330(4) 0.0380(5) 0.0409(5) 0.000 -0.0074(4) 0.000 N1 0.0448(10) 0.0393(11) 0.0278(8) -0.0022(9) -0.0014(8) 0.0081(10) O2 0.0283(12) 0.0535(15) 0.0593(13) 0.000 -0.0027(10) 0.000 O1 0.0498(13) 0.0469(13) 0.0344(11) 0.000 -0.0123(10) 0.000 C4 0.0339(11) 0.0281(12) 0.0323(11) 0.0002(11) -0.0060(9) -0.0014(11) C2 0.0407(13) 0.0421(14) 0.0302(10) 0.0032(10) -0.0029(9) -0.0017(12) C1 0.0297(11) 0.0301(12) 0.0332(11) -0.0001(10) -0.0058(9) -0.0044(11) C3 0.0379(12) 0.0378(14) 0.0334(11) -0.0052(10) 0.0009(9) 0.0042(11) C5 0.0398(13) 0.0385(14) 0.0305(11) 0.0054(10) 0.0029(9) -0.0002(12) C6 0.0316(11) 0.0390(14) 0.0377(11) -0.0033(11) 0.0023(10) -0.0012(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 O5 C8 1.202(2) . ? O3 C7 1.221(2) . ? C7 N1 1.344(2) . ? C7 C8 1.529(3) . ? C8 O4 1.307(2) . ? O4 H4 0.8200 . ? O2W H9 0.838(10) . ? O1W H7 0.833(10) . ? O1W H8 0.833(10) . ? S1 O1 1.4392(17) . ? S1 O2 1.441(2) . ? S1 C1 1.760(2) . ? S1 C1 1.760(2) 7_575 ? N1 C4 1.410(2) . ? N1 H1 0.8600 . ? C4 C3 1.381(2) . ? C4 C5 1.383(3) . ? C2 C1 1.377(3) . ? C2 C3 1.378(3) . ? C2 H2 0.9300 . ? C1 C6 1.386(2) . ? C3 H3 0.9300 . ? C5 C6 1.378(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? 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 O3 C7 N1 126.3(2) . . ? O3 C7 C8 121.4(2) . . ? N1 C7 C8 112.32(17) . . ? O5 C8 O4 125.8(2) . . ? O5 C8 C7 122.7(2) . . ? O4 C8 C7 111.55(18) . . ? C8 O4 H4 109.5 . . ? H7 O1W H8 109(2) . . ? O1 S1 O2 119.40(13) . . ? O1 S1 C1 108.37(9) . . ? O2 S1 C1 108.57(8) . . ? O1 S1 C1 108.37(9) . 7_575 ? O2 S1 C1 108.57(8) . 7_575 ? C1 S1 C1 102.21(13) . 7_575 ? C7 N1 C4 127.16(15) . . ? C7 N1 H1 116.4 . . ? C4 N1 H1 116.4 . . ? C3 C4 C5 120.6(2) . . ? C3 C4 N1 121.16(18) . . ? C5 C4 N1 118.11(16) . . ? C1 C2 C3 120.58(18) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C1 C6 120.27(19) . . ? C2 C1 S1 119.38(15) . . ? C6 C1 S1 120.03(16) . . ? C2 C3 C4 119.08(19) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C6 C5 C4 120.07(18) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 119.35(19) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.176 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 949944' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_CaH2L _audit_creation_date 2013-06-14T22:50:16-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H16 Ca1 N2 O11 S1' _chemical_formula_sum 'C16 H16 Ca N2 O11 S' _chemical_formula_weight 484.45 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.876(3) _cell_length_b 23.562(5) _cell_length_c 12.514(3) _cell_angle_alpha 90 _cell_angle_beta 117.77(3) _cell_angle_gamma 90 _cell_volume 4142.0(14) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4238 _cell_measurement_theta_min 3.6835 _cell_measurement_theta_max 62.2762 _cell_measurement_wavelength 1.5418 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.36 (release 16-03-2009 CrysAlis171 .NET) (compiled Mar 16 2009,17:39:00) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.6862 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10.4186 _diffrn_orient_matrix_ub_11 -0.1044442827 _diffrn_orient_matrix_ub_12 -0.0148067073 _diffrn_orient_matrix_ub_13 -0.0892084405 _diffrn_orient_matrix_ub_21 -0.0144668631 _diffrn_orient_matrix_ub_22 -0.0241632806 _diffrn_orient_matrix_ub_23 0.1060107001 _diffrn_orient_matrix_ub_31 -0.0313656015 _diffrn_orient_matrix_ub_32 0.0602818097 _diffrn_orient_matrix_ub_33 0.020294026 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_unetI/netI 0.0368 _diffrn_reflns_number 9686 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 61.86 _diffrn_reflns_theta_full 61.86 _diffrn_measured_fraction_theta_full 0.963 _diffrn_measured_fraction_theta_max 0.963 _reflns_number_total 3135 _reflns_number_gt 2406 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.36 (release 16-03-2009 CrysAlis171 .NET) (compiled Mar 16 2009,17:39:00) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.36 (release 16-03-2009 CrysAlis171 .NET) (compiled Mar 16 2009,17:39:00) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.36 (release 16-03-2009 CrysAlis171 .NET) (compiled Mar 16 2009,17:39:00) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0803P)^2^+9.1589P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3135 _refine_ls_number_parameters 294 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.067 _refine_ls_R_factor_gt 0.05 _refine_ls_wR_factor_ref 0.1436 _refine_ls_wR_factor_gt 0.1346 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 2.083 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.558 _refine_diff_density_min -0.93 _refine_diff_density_rms 0.072 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.3641 1.2855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C14 C 0.0419(6) 0.5738(4) 0.1219(9) 0.045(2) Uani 1 1 d . A . H14 H 0.0713 0.5602 0.2007 0.054 Uiso 1 1 calc R . . C9 C 0.0886(6) 0.6140(4) 0.0857(9) 0.048(3) Uani 1 1 d . . . C10 C 0.0479(7) 0.6343(5) -0.0320(10) 0.060(3) Uani 1 1 d . A . H10 H 0.0794 0.661 -0.0551 0.072 Uiso 1 1 calc R . . C13 C -0.0491(6) 0.5540(4) 0.0401(8) 0.041(2) Uani 1 1 d . . . H13 H -0.0811 0.5279 0.0638 0.049 Uiso 1 1 calc R A . C12 C -0.0901(6) 0.5748(4) -0.0778(8) 0.042(2) Uani 1 1 d . A . C11 C -0.0406(7) 0.6140(5) -0.1140(9) 0.059(3) Uani 1 1 d . . . H11 H -0.0678 0.6261 -0.1938 0.071 Uiso 1 1 calc R A . N2 N -0.1814(5) 0.5582(3) -0.1683(6) 0.0412(19) Uani 1 1 d . . . H2 H -0.1923 0.5638 -0.2415 0.049 Uiso 1 1 calc R A . C15 C -0.2537(5) 0.5347(3) -0.1552(7) 0.0285(18) Uani 1 1 d . A . O5 O -0.4198(4) 0.5193(2) -0.2697(4) 0.0271(12) Uani 1 1 d . . . O4 O -0.2522(4) 0.5209(2) -0.0583(5) 0.0326(13) Uani 1 1 d . . . C16 C -0.3447(6) 0.5278(3) -0.2786(7) 0.0276(18) Uani 1 1 d . . . O6 O -0.3327(4) 0.5313(2) -0.3707(5) 0.0341(13) Uani 1 1 d . . . Ca Ca -0.08309(11) 1.00424(6) 0.57367(13) 0.0237(5) Uani 1 1 d . . . S1A S 0.1991(3) 0.6437(3) 0.1860(7) 0.0367(14) Uani 0.773(19) 1 d P A 3 O1A O 0.2564(7) 0.5973(5) 0.2621(11) 0.043(3) Uani 0.773(19) 1 d P A 3 O2A O 0.2366(8) 0.6782(5) 0.1198(11) 0.041(3) Uani 0.773(19) 1 d P A 3 S1B S 0.2028(14) 0.6299(9) 0.224(2) 0.0367(14) Uani 0.227(19) 1 d P A 4 O1B O 0.248(3) 0.5815(16) 0.304(4) 0.043(3) Uani 0.227(19) 1 d P A 4 O2B O 0.251(3) 0.6583(19) 0.163(4) 0.041(3) Uani 0.227(19) 1 d P A 4 O2 O 0.0239(4) 0.8491(2) 0.6195(5) 0.0394(15) Uani 1 1 d D . . O3 O 0.1044(4) 0.8907(2) 0.4126(5) 0.0333(13) Uani 1 1 d . . . O1 O 0.0248(4) 0.9369(2) 0.5416(5) 0.0277(12) Uani 1 1 d . . . C2 C 0.0826(5) 0.8587(3) 0.4742(7) 0.0266(17) Uani 1 1 d . . . N1 N 0.0893(5) 0.8009(3) 0.4781(6) 0.0317(16) Uani 1 1 d . . . H1 H 0.074 0.7842 0.5276 0.038 Uiso 1 1 calc RD . . C8 C 0.1375(6) 0.7071(3) 0.4460(9) 0.039(2) Uani 1 1 d . . . H8 H 0.1319 0.6942 0.5127 0.046 Uiso 1 1 calc R . . C3 C 0.1187(5) 0.7646(3) 0.4103(7) 0.0312(19) Uani 1 1 d . A . C7 C 0.1645(6) 0.6696(4) 0.3806(9) 0.044(2) Uani 1 1 d . A . H7 H 0.1775 0.6317 0.4036 0.052 Uiso 1 1 calc R . . C1 C 0.0398(6) 0.8838(3) 0.5532(7) 0.0281(17) Uani 1 1 d . . . C6 C 0.1714(6) 0.6899(4) 0.2807(8) 0.040(2) Uani 1 1 d . . . C4 C 0.1272(6) 0.7845(4) 0.3102(8) 0.038(2) Uani 1 1 d . . . H4 H 0.1156 0.8224 0.2876 0.045 Uiso 1 1 calc R A . C5 C 0.1533(6) 0.7464(4) 0.2441(9) 0.045(2) Uani 1 1 d . A . H5 H 0.1584 0.7588 0.1769 0.054 Uiso 1 1 calc R . . O1W O -0.1194(4) 0.9104(2) 0.6216(5) 0.0352(14) Uani 1 1 d . . . H2W1 H -0.0782 0.8906 0.6336 0.053 Uiso 1 1 d R . . H1W1 H -0.1426 0.8973 0.6797 0.053 Uiso 1 1 d R . . O2W O -0.2600(5) 0.8561(3) 0.3834(6) 0.065(2) Uani 1 1 d . . . H1W2 H -0.2202 0.8723 0.4494 0.097 Uiso 1 1 d R . . H2W2 H -0.2262 0.8427 0.3515 0.097 Uiso 1 1 d R . . O3W1 O -0.3975(15) 0.7634(5) 0.2745(8) 0.256(14) Uani 0.88(4) 1 d PD B 1 H131 H -0.3421 0.7584 0.3375 0.384 Uiso 0.88(4) 1 d PRD B 1 H231 H -0.3955 0.743 0.2188 0.384 Uiso 0.88(4) 1 d PRD B 1 O3W2 O -0.544(10) 0.754(4) 0.254(19) 0.256(14) Uani 0.12(4) 1 d P . 2 H132 H -0.6052 0.7597 0.2181 0.384 Uiso 0.12(4) 1 d PR B 2 H232 H -0.5381 0.7192 0.2809 0.384 Uiso 0.12(4) 1 d PR 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 C14 0.035(5) 0.049(6) 0.040(6) -0.018(4) 0.008(4) 0.005(4) C9 0.028(5) 0.057(6) 0.058(7) -0.034(5) 0.019(5) -0.007(4) C10 0.039(6) 0.097(9) 0.050(7) -0.030(6) 0.026(5) -0.031(6) C13 0.036(5) 0.044(5) 0.038(5) -0.016(4) 0.013(4) -0.004(4) C12 0.035(5) 0.059(6) 0.033(5) -0.021(4) 0.017(4) -0.016(4) C11 0.047(6) 0.096(8) 0.042(6) -0.018(6) 0.028(5) -0.031(6) N2 0.034(4) 0.069(5) 0.024(4) -0.010(3) 0.016(3) -0.021(4) C15 0.028(4) 0.033(4) 0.026(4) -0.004(3) 0.014(4) 0.000(3) O5 0.025(3) 0.039(3) 0.020(3) -0.001(2) 0.013(2) -0.002(2) O4 0.031(3) 0.046(3) 0.021(3) 0.001(2) 0.012(3) -0.002(3) C16 0.031(4) 0.029(4) 0.022(4) 0.000(3) 0.011(4) -0.001(3) O6 0.036(3) 0.049(3) 0.019(3) -0.002(3) 0.015(3) -0.007(3) Ca 0.0250(8) 0.0297(9) 0.0182(8) -0.0010(6) 0.0115(6) 0.0000(6) S1A 0.0260(13) 0.043(3) 0.037(3) -0.015(2) 0.011(2) 0.0025(16) O1A 0.032(4) 0.042(6) 0.048(7) -0.011(5) 0.012(4) 0.006(4) O2A 0.030(5) 0.054(7) 0.046(7) -0.017(5) 0.022(6) -0.007(5) S1B 0.0260(13) 0.043(3) 0.037(3) -0.015(2) 0.011(2) 0.0025(16) O1B 0.032(4) 0.042(6) 0.048(7) -0.011(5) 0.012(4) 0.006(4) O2B 0.030(5) 0.054(7) 0.046(7) -0.017(5) 0.022(6) -0.007(5) O2 0.051(4) 0.034(3) 0.044(4) 0.007(3) 0.032(3) 0.005(3) O3 0.041(3) 0.031(3) 0.034(3) 0.001(2) 0.023(3) 0.005(3) O1 0.032(3) 0.027(3) 0.029(3) 0.002(2) 0.018(3) 0.002(2) C2 0.023(4) 0.030(4) 0.022(4) -0.002(3) 0.006(3) 0.000(3) N1 0.035(4) 0.029(4) 0.034(4) -0.003(3) 0.018(3) -0.001(3) C8 0.028(5) 0.034(5) 0.052(6) -0.008(4) 0.017(4) -0.006(4) C3 0.021(4) 0.034(5) 0.032(5) -0.008(4) 0.007(4) 0.001(3) C7 0.030(5) 0.029(5) 0.064(7) -0.015(4) 0.015(5) -0.003(4) C1 0.028(4) 0.030(4) 0.026(4) 0.000(3) 0.012(4) -0.001(3) C6 0.023(5) 0.048(5) 0.042(5) -0.018(4) 0.009(4) -0.001(4) C4 0.034(5) 0.042(5) 0.033(5) -0.005(4) 0.012(4) 0.008(4) C5 0.038(5) 0.051(6) 0.041(5) -0.013(4) 0.014(4) 0.004(4) O1W 0.035(3) 0.040(3) 0.036(3) 0.007(3) 0.022(3) 0.001(3) O2W 0.071(5) 0.079(5) 0.039(4) -0.009(4) 0.021(4) -0.024(4) O3W1 0.101(16) 0.048(7) 0.39(3) -0.016(11) -0.078(15) 0.019(8) O3W2 0.101(16) 0.048(7) 0.39(3) -0.016(11) -0.078(15) 0.019(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C14 C9 1.402(14) . ? C14 C13 1.405(12) . ? C9 C10 1.389(15) . ? C9 S1A 1.759(10) . ? C9 S1B 1.87(2) . ? C10 C11 1.383(13) . ? C13 C12 1.395(13) . ? C12 C11 1.416(13) . ? C12 N2 1.417(11) . ? N2 C15 1.351(10) . ? C15 O4 1.246(9) . ? C15 C16 1.556(11) . ? O5 C16 1.264(9) . ? O5 Ca 2.440(5) 3_444 ? O5 Ca 2.458(5) 4_445 ? O4 Ca 2.561(5) 4_445 ? C16 O6 1.255(9) . ? O6 Ca 2.403(6) 7_465 ? Ca O6 2.403(6) 7_465 ? Ca O1W 2.429(5) . ? Ca O5 2.440(5) 3_556 ? Ca O5 2.458(5) 4_455 ? Ca O1 2.470(5) 5_576 ? Ca O1 2.500(5) . ? Ca O3 2.515(5) 5_576 ? Ca O4 2.561(5) 4_455 ? Ca Ca 3.864(3) 5_576 ? Ca Ca 3.948(3) 2_556 ? S1A O1A 1.458(10) . ? S1A O2A 1.469(10) . ? S1A C6 1.807(10) . ? S1B O1B 1.47(4) . ? S1B O2B 1.48(4) . ? S1B C6 1.75(2) . ? O2 C1 1.270(9) . ? O3 C2 1.238(9) . ? O3 Ca 2.515(5) 5_576 ? O1 C1 1.271(9) . ? O1 Ca 2.470(5) 5_576 ? C2 N1 1.367(10) . ? C2 C1 1.553(11) . ? N1 C3 1.426(10) . ? C8 C7 1.400(12) . ? C8 C3 1.416(12) . ? C3 C4 1.402(12) . ? C7 C6 1.392(13) . ? C6 C5 1.392(13) . ? C4 C5 1.407(12) . ? O3W2 O3W2 1.4(4) 2_455 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 C14 C13 120.5(9) . . ? C10 C9 C14 121.4(8) . . ? C10 C9 S1A 115.9(8) . . ? C14 C9 S1A 122.7(9) . . ? C10 C9 S1B 133.2(11) . . ? C14 C9 S1B 105.4(10) . . ? S1A C9 S1B 17.4(6) . . ? C11 C10 C9 118.5(10) . . ? C12 C13 C14 117.9(9) . . ? C13 C12 C11 120.8(8) . . ? C13 C12 N2 123.2(8) . . ? C11 C12 N2 116.0(8) . . ? C10 C11 C12 120.8(10) . . ? C15 N2 C12 128.8(7) . . ? O4 C15 N2 126.4(7) . . ? O4 C15 C16 121.7(7) . . ? N2 C15 C16 111.8(6) . . ? C16 O5 Ca 130.2(5) . 3_444 ? C16 O5 Ca 122.1(5) . 4_445 ? Ca O5 Ca 107.41(19) 3_444 4_445 ? C15 O4 Ca 114.3(5) . 4_445 ? O6 C16 O5 130.1(7) . . ? O6 C16 C15 115.9(7) . . ? O5 C16 C15 114.0(6) . . ? C16 O6 Ca 134.4(5) . 7_465 ? O6 Ca O1W 82.23(19) 7_465 . ? O6 Ca O5 139.42(18) 7_465 3_556 ? O1W Ca O5 102.70(19) . 3_556 ? O6 Ca O5 147.93(18) 7_465 4_455 ? O1W Ca O5 77.35(18) . 4_455 ? O5 Ca O5 70.05(19) 3_556 4_455 ? O6 Ca O1 75.75(18) 7_465 5_576 ? O1W Ca O1 148.38(18) . 5_576 ? O5 Ca O1 80.82(18) 3_556 5_576 ? O5 Ca O1 131.61(18) 4_455 5_576 ? O6 Ca O1 72.24(19) 7_465 . ? O1W Ca O1 73.85(17) . . ? O5 Ca O1 70.74(17) 3_556 . ? O5 Ca O1 123.80(18) 4_455 . ? O1 Ca O1 77.95(18) 5_576 . ? O6 Ca O3 112.87(19) 7_465 5_576 ? O1W Ca O3 145.43(19) . 5_576 ? O5 Ca O3 85.91(18) 3_556 5_576 ? O5 Ca O3 74.34(17) 4_455 5_576 ? O1 Ca O3 65.60(17) 5_576 5_576 ? O1 Ca O3 139.43(18) . 5_576 ? O6 Ca O4 85.87(19) 7_465 4_455 ? O1W Ca O4 78.82(18) . 4_455 ? O5 Ca O4 134.71(17) 3_556 4_455 ? O5 Ca O4 66.18(17) 4_455 4_455 ? O1 Ca O4 121.16(18) 5_576 4_455 ? O1 Ca O4 146.82(18) . 4_455 ? O3 Ca O4 71.88(18) 5_576 4_455 ? O6 Ca Ca 69.23(13) 7_465 5_576 ? O1W Ca Ca 111.37(14) . 5_576 ? O5 Ca Ca 71.61(12) 3_556 5_576 ? O5 Ca Ca 141.67(14) 4_455 5_576 ? O1 Ca Ca 39.25(12) 5_576 5_576 ? O1 Ca Ca 38.70(12) . 5_576 ? O3 Ca Ca 103.14(13) 5_576 5_576 ? O4 Ca Ca 150.72(14) 4_455 5_576 ? O6 Ca Ca 159.13(14) 7_465 2_556 ? O1W Ca Ca 80.55(14) . 2_556 ? O5 Ca Ca 36.45(12) 3_556 2_556 ? O5 Ca Ca 36.14(12) 4_455 2_556 ? O1 Ca Ca 114.56(14) 5_576 2_556 ? O1 Ca Ca 91.63(13) . 2_556 ? O3 Ca Ca 87.98(13) 5_576 2_556 ? O4 Ca Ca 102.18(13) 4_455 2_556 ? Ca Ca Ca 106.51(7) 5_576 2_556 ? O1A S1A O2A 119.3(6) . . ? O1A S1A C9 106.1(6) . . ? O2A S1A C9 110.4(6) . . ? O1A S1A C6 107.0(6) . . ? O2A S1A C6 108.8(6) . . ? C9 S1A C6 104.0(4) . . ? O1B S1B O2B 120(2) . . ? O1B S1B C6 119.6(17) . . ? O2B S1B C6 99(2) . . ? O1B S1B C9 116(2) . . ? O2B S1B C9 96.9(19) . . ? C6 S1B C9 101.5(11) . . ? C2 O3 Ca 118.1(5) . 5_576 ? C1 O1 Ca 121.3(5) . 5_576 ? C1 O1 Ca 135.4(5) . . ? Ca O1 Ca 102.05(18) 5_576 . ? O3 C2 N1 126.1(7) . . ? O3 C2 C1 119.9(6) . . ? N1 C2 C1 114.0(7) . . ? C2 N1 C3 128.2(7) . . ? C7 C8 C3 119.9(9) . . ? C4 C3 C8 120.5(7) . . ? C4 C3 N1 121.7(7) . . ? C8 C3 N1 117.8(7) . . ? C6 C7 C8 118.8(8) . . ? O2 C1 O1 128.7(7) . . ? O2 C1 C2 116.8(6) . . ? O1 C1 C2 114.5(6) . . ? C7 C6 C5 122.3(8) . . ? C7 C6 S1B 103.8(10) . . ? C5 C6 S1B 133.9(11) . . ? C7 C6 S1A 121.8(7) . . ? C5 C6 S1A 115.9(8) . . ? S1B C6 S1A 18.0(6) . . ? C3 C4 C5 119.3(8) . . ? C6 C5 C4 119.3(9) . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 949945'