Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Banwell, M.' 'Edwards, A. J.' 'Jolliffe, Katrina A.' 'Kemmler, Michael' _publ_contact_author_name 'Prof M Banwell' _publ_contact_author_address ; Prof M Banwell The Research School of Chemistry Australian National University Canberra ACT 0200 AUSTRALIA ; _publ_contact_author_email 'mgb@rsc.anu.edu.au' _publ_contact_author_fax ' australia + 2 6125 8114' _publ_contact_author_phone 'australia + 2 6125 8202' _journal_name_full 'Journal of the Chemical Society, Perkin Trans. 1' _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Waasmaier, D. & Kirfel, A. (1995). Acta Cryst. A51, 416-431. Coppens, P. (1970). In Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P.Huber, pp 255-270. Copenhagen: Munksgaard. Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699 Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; data_mbmk3z _database_code_CSD 160053 _audit_creation_method 'maXus + CRYSTALS_ver_12-03-99' _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'prism' _exptl_crystal_colour 'Colourless' _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment 'refU' # Submission details _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) maxus(Mackay et al., 1999) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 0.01443 _diffrn_orient_matrix_UB_12 0.03317 _diffrn_orient_matrix_UB_13 -0.06809 _diffrn_orient_matrix_UB_21 -0.09678 _diffrn_orient_matrix_UB_22 0.01736 _diffrn_orient_matrix_UB_23 -0.00467 _diffrn_orient_matrix_UB_31 0.02432 _diffrn_orient_matrix_UB_32 0.04939 _diffrn_orient_matrix_UB_33 0.04736 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.37 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 397.492 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,-Y,-Z' '-X+ 1/2,+Y+ 1/2,-Z+ 1/2' '+X+ 1/2,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_cell_setting 'Monoclinic' _chemical_formula_moiety 'C22 H23 N O4 S ' _chemical_formula_sum 'C22 H23 N O4 S ' _chemical_name_systematic ; ? ; _cell_length_a 9.9458(2) _cell_length_b 16.1368(4) _cell_length_c 12.0708(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.2552(13) _cell_angle_gamma 90.00 _cell_volume 1931.94(8) _diffrn_reflns_number 31879 _diffrn_reflns_theta_max 27.49 _cell_measurement_reflns_used 19451 _cell_measurement_theta_min 2.546 _cell_measurement_theta_max 27.485 _diffrn_measurement_method 'CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 -1 0.090 0 -1 1 0.080 1 0 0 0.200 -1 0 0 0.150 0 -2 -1 0.080 0 2 1 0.100 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.946 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_reflns_av_R_equivalents 0.049 _exptl_absorpt_coefficient_mu 0.196 _exptl_crystal_F_000 824 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' 'S ' 0.1100 0.1240 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International_Tables_Vol_IV_Table_2.2B' # Refinement statistics _reflns_d_resolution_low 1.99 _reflns_d_resolution_high 0.62 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _reflns_number_total 4414 _reflns_threshold_expression >3.00\s(I) _reflns_number_gt 3733 _refine_ls_number_reflns 3733 _refine_ls_number_parameters 270 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0291 _refine_ls_goodness_of_fit_ref 1.0315 _refine_ls_shift/su_max 0.000675 _refine_ls_structure_factor_coef F _refine_diff_density_min -0.45 _refine_diff_density_max 0.34 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 4 parameters, Carruthers & Watkin , 1979, -.254E-01-.802 -.394 -.417 ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type S8 0.74189(3) 0.22032(2) 0.82131(3) 0.0378 1.0000 Uani O19 0.8707(1) 0.00764(9) 1.42407(8) 0.0569 1.0000 Uani O21 0.67889(11) 0.03554(9) 1.51447(9) 0.0587 1.0000 Uani O25 0.8018(1) 0.19780(8) 0.72157(9) 0.0500 1.0000 Uani O26 0.77453(11) 0.29768(7) 0.87524(11) 0.0531 1.0000 Uani N1 0.7832(1) 0.14803(6) 0.91206(9) 0.0321 1.0000 Uani C2 0.74779(14) 0.16003(8) 1.02777(11) 0.0353 1.0000 Uani C3 0.65724(12) 0.08576(8) 1.0526(1) 0.0299 1.0000 Uani C4 0.74216(13) -0.05928(8) 1.00612(11) 0.0344 1.0000 Uani C5 0.81769(15) -0.11571(9) 0.93350(12) 0.0419 1.0000 Uani C6 0.85278(14) -0.07467(9) 0.82510(12) 0.0400 1.0000 Uani C7 0.88553(12) 0.01720(8) 0.84041(11) 0.0345 1.0000 Uani C9 0.56541(13) 0.21640(8) 0.79336(12) 0.0380 1.0000 Uani C10 0.51095(13) 0.17051(9) 0.70346(12) 0.0427 1.0000 Uani C11 0.37122(15) 0.1637(1) 0.68594(15) 0.0493 1.0000 Uani C12 0.28638(14) 0.2010(1) 0.75693(16) 0.0516 1.0000 Uani C13 0.13543(16) 0.19004(12) 0.7389(2) 0.0699 1.0000 Uani C14 0.34300(16) 0.2478(1) 0.84463(16) 0.0534 1.0000 Uani C15 0.48180(15) 0.25597(9) 0.86389(14) 0.0463 1.0000 Uani C16 0.65595(12) 0.06943(7) 1.1755(1) 0.0295 1.0000 Uani C17 0.77365(12) 0.04250(8) 1.2361(1) 0.0330 1.0000 Uani C18 0.76946(12) 0.03445(9) 1.3485(1) 0.0356 1.0000 Uani C20 0.82029(17) 0.02003(14) 1.53042(13) 0.0599 1.0000 Uani C22 0.65484(14) 0.05127(9) 1.40252(11) 0.0389 1.0000 Uani C23 0.53843(13) 0.0776(1) 1.34586(12) 0.0427 1.0000 Uani C24 0.54109(13) 0.08618(9) 1.23077(11) 0.0371 1.0000 Uani C31 0.71663(11) 0.01949(7) 0.98189(9) 0.0278 1.0000 Uani C71 0.76094(12) 0.06002(8) 0.8780(1) 0.0293 1.0000 Uani H21 0.83084(14) 0.16049(8) 1.07982(11) 0.050(3) 1.0000 Uiso H22 0.69762(14) 0.21323(8) 1.03497(11) 0.050(3) 1.0000 Uiso H31 0.55828(12) 0.09227(8) 1.0333(1) 0.047(4) 1.0000 Uiso H41 0.71005(13) -0.08223(8) 1.07644(11) 0.051(5) 1.0000 Uiso H51 0.90317(15) -0.13352(9) 0.97564(12) 0.049(3) 1.0000 Uiso H52 0.76031(15) -0.16540(9) 0.91490(12) 0.049(3) 1.0000 Uiso H61 0.93287(14) -0.10348(9) 0.79762(12) 0.047(3) 1.0000 Uiso H62 0.77426(14) -0.08039(9) 0.76890(12) 0.047(3) 1.0000 Uiso H71 0.96235(12) 0.02414(8) 0.89796(11) 0.047(3) 1.0000 Uiso H72 0.91042(12) 0.04150(8) 0.76852(11) 0.047(3) 1.0000 Uiso H101 0.57124(13) 0.14295(9) 0.65192(12) 0.050(5) 1.0000 Uiso H111 0.33160(15) 0.1313(1) 0.62087(15) 0.054(5) 1.0000 Uiso H131 0.09015(16) 0.22093(12) 0.7975(2) 0.113(6) 1.0000 Uiso H132 0.11261(16) 0.12981(12) 0.7430(2) 0.113(6) 1.0000 Uiso H133 0.10367(16) 0.21210(12) 0.6640(2) 0.113(6) 1.0000 Uiso H141 0.28242(16) 0.2762(1) 0.89517(16) 0.070(6) 1.0000 Uiso H151 0.52094(15) 0.28986(9) 0.92773(14) 0.057(5) 1.0000 Uiso H171 0.85730(12) 0.02947(8) 1.1984(1) 0.061(5) 1.0000 Uiso H201 0.86657(17) 0.06847(14) 1.56823(13) 0.076(4) 1.0000 Uiso H202 0.83666(17) -0.03073(14) 1.57700(13) 0.076(4) 1.0000 Uiso H231 0.45551(13) 0.0899(1) 1.38494(12) 0.061(5) 1.0000 Uiso H241 0.45765(13) 0.10510(9) 1.18666(11) 0.048(4) 1.0000 Uiso H711 0.69438(12) 0.05622(8) 0.8119(1) 0.048(4) 1.0000 Uiso 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 S8 0.03110(17) 0.03699(18) 0.04485(19) 0.01695(13) -0.00047(12) -0.00487(12) O19 0.0419(6) 0.100(1) 0.0284(5) 0.0045(5) -0.0002(4) 0.0188(6) O21 0.0508(6) 0.097(1) 0.0297(5) 0.0049(5) 0.0101(4) 0.0074(6) O25 0.0365(5) 0.0703(7) 0.0439(6) 0.0252(5) 0.0074(4) -0.0020(5) O26 0.0498(6) 0.0336(5) 0.0737(8) 0.0172(5) -0.0101(5) -0.0119(4) N1 0.0353(5) 0.0286(5) 0.0320(5) 0.0057(4) 0.0001(4) -0.0022(4) C2 0.0449(7) 0.0284(6) 0.0324(6) -0.0001(5) 0.0011(5) -0.0013(5) C3 0.0281(5) 0.0314(6) 0.0300(6) 0.0010(4) 0.0007(4) 0.0026(4) C4 0.0399(6) 0.0302(6) 0.0327(6) 0.0011(5) 0.0004(5) -0.0031(5) C5 0.0499(8) 0.0310(6) 0.0442(7) -0.0062(5) -0.0006(6) 0.0026(6) C6 0.0378(7) 0.0430(7) 0.0394(7) -0.0134(5) 0.0034(5) -0.0012(5) C7 0.0320(6) 0.0413(7) 0.0304(6) -0.0042(5) 0.0039(5) -0.0025(5) C9 0.0318(6) 0.0343(6) 0.0479(8) 0.0152(5) 0.0018(5) 0.0000(5) C10 0.0350(7) 0.0444(7) 0.0477(8) 0.0128(6) -0.0036(6) 0.0001(6) C11 0.0382(7) 0.0463(8) 0.062(1) 0.0187(7) -0.0073(6) -0.0033(6) C12 0.0326(7) 0.0409(8) 0.0807(11) 0.0311(8) 0.0010(7) -0.0003(6) C13 0.0329(7) 0.0613(11) 0.1150(17) 0.0426(11) 0.0017(8) 0.0006(7) C14 0.0430(7) 0.0376(8) 0.0813(12) 0.0193(8) 0.0166(8) 0.0077(6) C15 0.0443(7) 0.0335(7) 0.0615(9) 0.0100(6) 0.0073(7) 0.0030(6) C16 0.0280(5) 0.0313(6) 0.0293(6) 0.0000(4) 0.0030(4) 0.0020(4) C17 0.0284(6) 0.0417(7) 0.0293(6) -0.0009(5) 0.0053(5) 0.0043(5) C18 0.0314(6) 0.0461(7) 0.0292(6) 0.0010(5) 0.0020(5) 0.0032(5) C20 0.0532(9) 0.0976(15) 0.0290(7) 0.0032(8) 0.0028(6) 0.0096(9) C22 0.0397(7) 0.0500(8) 0.0280(6) -0.0007(5) 0.0095(5) 0.0000(6) C23 0.0324(6) 0.0569(9) 0.0405(7) 0.0009(6) 0.0135(5) 0.0048(6) C24 0.0276(6) 0.0460(7) 0.0381(7) 0.0020(5) 0.0058(5) 0.0053(5) C31 0.0271(5) 0.0301(6) 0.0262(5) 0.0001(4) 0.0006(4) -0.0043(4) C71 0.0292(6) 0.0322(6) 0.0261(5) 0.0013(4) -0.0004(4) -0.0027(4) _refine_ls_extinction_coef 255.3(364) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S8 . O25 . 1.4295(12) yes S8 . O26 . 1.4340(12) yes S8 . N1 . 1.632(1) yes S8 . C9 . 1.7637(13) yes O19 . C18 . 1.3774(15) yes O19 . C20 . 1.4264(18) yes O21 . C20 . 1.4273(19) yes O21 . C22 . 1.3783(16) yes N1 . C2 . 1.4784(16) yes N1 . C71 . 1.4906(16) yes C2 . C3 . 1.5419(17) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C16 . 1.5072(17) yes C3 . C31 . 1.5154(16) yes C3 . H31 . 1.000 no C4 . C5 . 1.5032(19) yes C4 . C31 . 1.3246(17) yes C4 . H41 . 1.000 no C5 . C6 . 1.530(2) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C7 . 1.5262(18) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C71 . 1.5172(17) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C9 . C10 . 1.390(2) yes C9 . C15 . 1.389(2) yes C10 . C11 . 1.3944(19) yes C10 . H101 . 1.000 no C11 . C12 . 1.384(3) yes C11 . H111 . 1.000 no C12 . C13 . 1.511(2) yes C12 . C14 . 1.386(3) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C14 . C15 . 1.389(2) yes C14 . H141 . 1.000 no C15 . H151 . 1.000 no C16 . C17 . 1.4028(16) yes C16 . C24 . 1.3916(17) yes C17 . C18 . 1.3659(17) yes C17 . H171 . 1.000 no C18 . C22 . 1.3818(18) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C22 . C23 . 1.3678(19) yes C23 . C24 . 1.3984(19) yes C23 . H231 . 1.000 no C24 . H241 . 1.000 no C31 . C71 . 1.5089(16) yes C71 . H711 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O25 . S8 . O26 . 120.61(7) yes O25 . S8 . N1 . 106.47(6) yes O26 . S8 . N1 . 106.27(6) yes O25 . S8 . C9 . 107.52(7) yes O26 . S8 . C9 . 107.86(7) yes N1 . S8 . C9 . 107.48(6) yes C18 . O19 . C20 . 105.30(11) yes C20 . O21 . C22 . 105.20(11) yes S8 . N1 . C2 . 118.34(9) yes S8 . N1 . C71 . 118.10(8) yes C2 . N1 . C71 . 110.14(9) yes N1 . C2 . C3 . 105.41(9) yes N1 . C2 . H21 . 110.53(7) no C3 . C2 . H21 . 110.52(6) no N1 . C2 . H22 . 110.49(6) no C3 . C2 . H22 . 110.36(7) no H21 . C2 . H22 . 109.467 no C2 . C3 . C16 . 112.0(1) yes C2 . C3 . C31 . 100.44(9) yes C16 . C3 . C31 . 117.6(1) yes C2 . C3 . H31 . 116.87(7) no C16 . C3 . H31 . 99.65(6) no C31 . C3 . H31 . 111.15(6) no C5 . C4 . C31 . 123.26(12) yes C5 . C4 . H41 . 118.40(8) no C31 . C4 . H41 . 118.35(8) no C4 . C5 . C6 . 113.09(11) yes C4 . C5 . H51 . 108.68(7) no C6 . C5 . H51 . 108.68(8) no C4 . C5 . H52 . 108.37(8) no C6 . C5 . H52 . 108.52(7) no H51 . C5 . H52 . 109.467 no C5 . C6 . C7 . 112.16(11) yes C5 . C6 . H61 . 108.69(7) no C7 . C6 . H61 . 108.89(7) no C5 . C6 . H62 . 108.91(7) no C7 . C6 . H62 . 108.71(7) no H61 . C6 . H62 . 109.467 no C6 . C7 . C71 . 107.9(1) yes C6 . C7 . H71 . 109.76(7) no C71 . C7 . H71 . 109.88(6) no C6 . C7 . H72 . 109.89(7) no C71 . C7 . H72 . 109.95(7) no H71 . C7 . H72 . 109.467 no S8 . C9 . C10 . 119.54(11) yes S8 . C9 . C15 . 119.93(12) yes C10 . C9 . C15 . 120.47(13) yes C9 . C10 . C11 . 119.11(15) yes C9 . C10 . H101 . 120.38(8) no C11 . C10 . H101 . 120.5(1) no C10 . C11 . C12 . 121.23(16) yes C10 . C11 . H111 . 119.4(1) no C12 . C11 . H111 . 119.40(9) no C11 . C12 . C13 . 120.29(17) yes C11 . C12 . C14 . 118.56(13) yes C13 . C12 . C14 . 121.15(17) yes C12 . C13 . H131 . 109.51(12) no C12 . C13 . H132 . 109.47(9) no H131 . C13 . H132 . 109.476 no C12 . C13 . H133 . 109.4(1) no H131 . C13 . H133 . 109.476 no H132 . C13 . H133 . 109.476 no C12 . C14 . C15 . 121.47(16) yes C12 . C14 . H141 . 119.13(9) no C15 . C14 . H141 . 119.39(11) no C9 . C15 . C14 . 119.12(16) yes C9 . C15 . H151 . 120.48(9) no C14 . C15 . H151 . 120.40(11) no C3 . C16 . C17 . 120.0(1) yes C3 . C16 . C24 . 120.34(11) yes C17 . C16 . C24 . 119.52(11) yes C16 . C17 . C18 . 117.50(11) yes C16 . C17 . H171 . 121.18(7) no C18 . C17 . H171 . 121.32(7) no O19 . C18 . C17 . 127.81(12) yes O19 . C18 . C22 . 109.69(11) yes C17 . C18 . C22 . 122.48(12) yes O19 . C20 . O21 . 108.16(12) yes O19 . C20 . H201 . 109.9(1) no O21 . C20 . H201 . 109.89(11) no O19 . C20 . H202 . 109.7(1) no O21 . C20 . H202 . 109.7(1) no H201 . C20 . H202 . 109.467 no O21 . C22 . C18 . 109.73(12) yes O21 . C22 . C23 . 128.77(13) yes C18 . C22 . C23 . 121.48(12) yes C22 . C23 . C24 . 116.73(12) yes C22 . C23 . H231 . 121.54(8) no C24 . C23 . H231 . 121.73(7) no C16 . C24 . C23 . 122.27(12) yes C16 . C24 . H241 . 118.83(7) no C23 . C24 . H241 . 118.89(7) no C3 . C31 . C4 . 128.99(11) yes C3 . C31 . C71 . 108.2(1) yes C4 . C31 . C71 . 122.44(11) yes N1 . C71 . C7 . 114.1(1) yes N1 . C71 . C31 . 103.32(9) yes C7 . C71 . C31 . 110.3(1) yes N1 . C71 . H711 . 110.77(6) no C7 . C71 . H711 . 103.92(6) no C31 . C71 . H711 . 114.80(6) no # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_mbkj1z _database_code_CSD 160054 _audit_creation_method 'maXus + CRYSTALS_ver_12-03-99' _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'Prism' _exptl_crystal_colour 'Colourless' _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment 'mixed' # Submission details _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 0.00424 _diffrn_orient_matrix_UB_12 0.03131 _diffrn_orient_matrix_UB_13 0.06546 _diffrn_orient_matrix_UB_21 -0.10645 _diffrn_orient_matrix_UB_22 0.00221 _diffrn_orient_matrix_UB_23 -0.01718 _diffrn_orient_matrix_UB_31 -0.00391 _diffrn_orient_matrix_UB_32 -0.02631 _diffrn_orient_matrix_UB_33 0.07646 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 457.545 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,-Y,-Z' '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_cell_setting 'Monoclinic' _chemical_formula_moiety 'C24 H27 N O6 S ' _chemical_formula_sum 'C24 H27 N O6 S ' _chemical_name_systematic ; ? ; _cell_length_a 9.51220(10) _cell_length_b 24.4129(3) _cell_length_c 9.93130(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.5571(6) _cell_angle_gamma 90.00 _cell_volume 2274.24(4) _diffrn_reflns_number 42162 _diffrn_reflns_theta_max 27.48 _cell_measurement_reflns_used 43893 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _diffrn_measurement_method 'CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.050 0 -1 0 0.030 0 0 -1 0.170 0 0 1 0.120 -1 0 0 0.080 1 0 0 0.100 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.955 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_reflns_av_R_equivalents 0.050 _exptl_absorpt_coefficient_mu 0.18 _exptl_crystal_F_000 969 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' 'S ' 0.1100 0.1240 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International_Tables_Vol_IV_Table_2.2B' # Refinement statistics _reflns_d_resolution_low 1.66 _reflns_d_resolution_high 0.62 _reflns_limit_h_max 12 _reflns_limit_h_min -12 _reflns_limit_k_max 31 _reflns_limit_k_min 0 _reflns_limit_l_max 12 _reflns_limit_l_min 0 _refine_ls_matrix_type full _reflns_number_total 5323 _reflns_number_gt 3319 _refine_ls_number_reflns 3319 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_parameters 283 _refine_ls_R_factor_gt 0.0688 _refine_ls_wR_factor_ref 0.0746 _refine_ls_goodness_of_fit_ref 1.0311 _refine_ls_shift/su_max 0.000678 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 5 parameters, Carruthers & Watkin , 1979, 1.16 0.634 0.858 -.180E-010.173 ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 _refine_diff_density_min -1.28 _refine_diff_density_max 1.58 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type S20 0.70204(8) 0.25199(3) 0.14053(7) 0.0357 1.0000 Uani O3 0.8797(3) 0.07456(14) -0.0662(3) 0.0665 1.0000 Uani O4 0.6897(2) 0.0444(1) 0.0180(2) 0.0428 1.0000 Uani O21 0.6316(3) 0.3042(1) 0.1303(3) 0.0496 1.0000 Uani O22 0.6897(3) 0.21690(11) 0.0223(2) 0.0504 1.0000 Uani O33 0.2136(2) 0.1542(1) 0.5054(2) 0.0446 1.0000 Uani O35 0.0364(2) 0.1149(1) 0.3480(2) 0.0420 1.0000 Uani N19 0.6392(2) 0.2184(1) 0.2570(3) 0.0338 1.0000 Uani C1 0.7577(4) 0.06000(14) -0.0844(4) 0.0459 1.0000 Uani C2 0.6619(6) 0.0578(2) -0.2191(4) 0.0682 1.0000 Uani C11 0.7716(3) 0.04815(14) 0.1560(3) 0.0423 1.0000 Uani C12 0.6662(3) 0.06301(13) 0.2492(3) 0.0364 1.0000 Uani C13 0.6508(4) 0.03209(15) 0.3535(4) 0.0489 1.0000 Uani C17 0.5917(3) 0.11779(12) 0.2184(3) 0.0325 1.0000 Uani C18 0.6900(3) 0.16245(12) 0.2926(3) 0.0331 1.0000 Uani C23 0.8856(3) 0.26390(13) 0.1965(3) 0.0338 1.0000 Uani C24 0.9881(3) 0.23141(14) 0.1520(3) 0.0388 1.0000 Uani C25 1.1311(3) 0.24210(13) 0.1964(3) 0.0422 1.0000 Uani C26 1.1738(3) 0.28512(14) 0.2869(3) 0.0410 1.0000 Uani C27 1.3289(4) 0.29600(19) 0.3356(5) 0.0585 1.0000 Uani C28 1.0691(3) 0.31673(14) 0.3316(3) 0.0415 1.0000 Uani C29 0.9257(3) 0.30670(13) 0.2870(3) 0.0385 1.0000 Uani C30 0.4415(3) 0.11796(12) 0.2523(3) 0.0319 1.0000 Uani C31 0.4094(3) 0.13915(13) 0.3745(3) 0.0333 1.0000 Uani C32 0.2698(3) 0.13623(12) 0.3943(3) 0.0320 1.0000 Uani C34 0.0634(3) 0.15077(17) 0.4641(4) 0.0467 1.0000 Uani C36 0.1643(3) 0.11257(12) 0.3000(3) 0.0333 1.0000 Uani C37 0.1925(3) 0.09120(14) 0.1798(3) 0.0384 1.0000 Uani C38 0.3337(3) 0.09474(13) 0.1581(3) 0.0375 1.0000 Uani C140 0.7032(18) -0.0277(5) 0.3722(11) 0.0688(9) 0.3179(9) Uiso C141 0.7310(7) -0.0204(3) 0.3941(7) 0.0688(9) 0.6821(9) Uiso C150 0.7746(14) -0.0447(4) 0.2499(12) 0.0688(9) 0.3179(9) Uiso C151 0.8698(6) -0.0206(2) 0.3374(6) 0.0688(9) 0.6821(9) Uiso C160 0.8655(8) 0.0026(5) 0.2112(15) 0.0688(9) 0.3179(9) Uiso C161 0.8395(7) -0.0094(3) 0.1837(6) 0.0688(9) 0.6821(9) Uiso H21 0.7152(6) 0.0697(2) -0.2928(4) 0.0840 1.0000 Uiso H22 0.6274(6) 0.0194(2) -0.2370(4) 0.0840 1.0000 Uiso H23 0.5786(6) 0.0827(2) -0.2178(4) 0.0840 1.0000 Uiso H111 0.8458(3) 0.07754(14) 0.1647(3) 0.0475 1.0000 Uiso H131 0.5822(4) 0.04525(15) 0.4125(4) 0.0573 1.0000 Uiso H171 0.5752(3) 0.12632(12) 0.1185(3) 0.0401 1.0000 Uiso H181 0.7869(3) 0.15819(12) 0.2673(3) 0.0400 1.0000 Uiso H182 0.6961(3) 0.15676(12) 0.3932(3) 0.0400 1.0000 Uiso H241 0.9587(3) 0.20077(14) 0.0866(3) 0.0464 1.0000 Uiso H251 1.2052(3) 0.21891(13) 0.1635(3) 0.0473 1.0000 Uiso H271 1.3376(4) 0.32788(19) 0.3996(5) 0.0647 1.0000 Uiso H272 1.3772(4) 0.30483(19) 0.2562(5) 0.0647 1.0000 Uiso H273 1.3748(4) 0.26311(19) 0.3844(5) 0.0647 1.0000 Uiso H281 1.0981(3) 0.34713(14) 0.3979(3) 0.0476 1.0000 Uiso H291 0.8513(3) 0.33024(13) 0.3182(3) 0.0501 1.0000 Uiso H311 0.4851(3) 0.15554(13) 0.4449(3) 0.0361 1.0000 Uiso H341 0.0224(3) 0.18782(17) 0.4389(4) 0.0548 1.0000 Uiso H342 0.0187(3) 0.13534(17) 0.5402(4) 0.0548 1.0000 Uiso H371 0.1158(3) 0.07397(14) 0.1119(3) 0.0461 1.0000 Uiso H381 0.3587(3) 0.08026(13) 0.0709(3) 0.0432 1.0000 Uiso H1 0.6423(2) 0.2385(1) 0.3283(3) 0.085(17) 1.0000 Uiso H160 0.9324(8) 0.0150(5) 0.2941(15) 0.0827(9) 0.3179(9) Uiso H161 0.9213(8) -0.0100(5) 0.1401(15) 0.0827(9) 0.3179(9) Uiso H162 0.9305(7) -0.0110(3) 0.1459(6) 0.0844(9) 0.6821(9) Uiso H163 0.7719(7) -0.0377(3) 0.1381(6) 0.0844(9) 0.6821(9) Uiso H150 0.8363(14) -0.0775(4) 0.2753(12) 0.0827(9) 0.3179(9) Uiso H151 0.6994(14) -0.0539(4) 0.1702(12) 0.0827(9) 0.3179(9) Uiso H152 0.9352(6) 0.0083(2) 0.3835(6) 0.0844(9) 0.6821(9) Uiso H153 0.9162(6) -0.0573(2) 0.3539(6) 0.0844(9) 0.6821(9) Uiso H140 0.7735(18) -0.0311(5) 0.4586(11) 0.0827(9) 0.3179(9) Uiso H141 0.6197(18) -0.0520(5) 0.3769(11) 0.0827(9) 0.3179(9) Uiso H142 0.7530(7) -0.0225(3) 0.4960(7) 0.0844(9) 0.6821(9) Uiso H143 0.6713(7) -0.0525(3) 0.3579(7) 0.0844(9) 0.6821(9) Uiso 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 S20 0.0324(3) 0.0430(4) 0.0309(3) 0.0071(3) 0.0027(2) -0.0004(3) O3 0.0540(16) 0.082(2) 0.0684(18) 0.0118(16) 0.0237(13) -0.0045(15) O4 0.0398(12) 0.0477(13) 0.0423(12) -0.010(1) 0.0106(9) -0.006(1) O21 0.0412(12) 0.0476(14) 0.0571(14) 0.0209(11) 0.000(1) 0.003(1) O22 0.0487(13) 0.0672(17) 0.0347(12) -0.0013(11) 0.005(1) -0.0063(12) O33 0.0366(11) 0.0629(15) 0.0358(11) -0.012(1) 0.0104(9) 0.004(1) O35 0.026(1) 0.0507(13) 0.0507(13) -0.009(1) 0.0109(9) -0.0023(9) N19 0.0301(12) 0.0342(13) 0.0376(13) 0.0026(11) 0.007(1) -0.000(1) C1 0.0488(19) 0.0406(17) 0.0511(19) -0.0017(14) 0.0165(15) 0.0002(15) C2 0.087(3) 0.070(3) 0.047(2) -0.002(2) 0.011(2) -0.006(2) C11 0.0333(15) 0.0489(18) 0.0449(17) -0.0076(14) 0.0073(13) 0.0064(13) C12 0.0305(14) 0.0379(16) 0.0411(16) -0.0059(13) 0.0064(12) 0.0000(12) C13 0.055(2) 0.0438(18) 0.0512(19) 0.0062(15) 0.0176(16) 0.0087(16) C17 0.0302(13) 0.0370(15) 0.0308(14) 0.0004(11) 0.0063(11) 0.0013(11) C18 0.0268(13) 0.0355(15) 0.0375(15) 0.0053(12) 0.0062(11) 0.0032(11) C23 0.0312(13) 0.0394(15) 0.0309(14) 0.0069(12) 0.0062(11) -0.0022(12) C24 0.0416(16) 0.0399(16) 0.0358(15) 0.0036(13) 0.0092(13) -0.0021(13) C25 0.0394(15) 0.0419(18) 0.0485(18) 0.0078(14) 0.0164(13) 0.0076(13) C26 0.0364(16) 0.0450(18) 0.0430(17) 0.0085(14) 0.0105(13) -0.0020(13) C27 0.0341(17) 0.069(2) 0.072(3) -0.000(2) 0.0072(16) -0.0049(16) C28 0.0413(16) 0.0461(18) 0.0387(16) -0.0033(14) 0.0108(13) -0.0073(14) C29 0.0359(15) 0.0429(17) 0.0384(15) 0.0019(13) 0.0113(12) -0.0010(13) C30 0.0265(13) 0.0326(14) 0.0366(14) 0.0002(11) 0.0051(11) 0.0013(11) C31 0.0260(13) 0.0394(15) 0.0333(14) -0.0045(12) 0.0016(11) -0.0023(11) C32 0.0309(14) 0.0351(15) 0.0301(13) -0.0030(11) 0.0051(11) 0.0036(11) C34 0.0360(16) 0.066(2) 0.0405(17) -0.0070(16) 0.0133(13) 0.0055(15) C36 0.0252(12) 0.0330(14) 0.0416(15) -0.0039(12) 0.0055(11) 0.0002(11) C37 0.0302(14) 0.0447(17) 0.0390(16) -0.0114(13) 0.0021(12) -0.0039(12) C38 0.0380(15) 0.0419(17) 0.0328(15) -0.0090(12) 0.0062(12) 0.0003(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S20 . O21 . 1.435(3) yes S20 . O22 . 1.442(3) yes S20 . N19 . 1.612(2) yes S20 . C23 . 1.766(3) yes O3 . C1 . 1.198(5) yes O4 . C1 . 1.348(4) yes O4 . C11 . 1.462(4) yes O33 . C32 . 1.376(3) yes O33 . C34 . 1.422(4) yes O35 . C34 . 1.437(4) yes O35 . C36 . 1.380(3) yes N19 . C18 . 1.473(4) yes N19 . H1 . 0.858 no C1 . C2 . 1.489(6) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C2 . H23 . 1.000 no C11 . C12 . 1.518(4) yes C11 . C160 . 1.473(12) yes C11 . C161 . 1.551(7) yes C11 . H111 . 1.000 no C12 . C13 . 1.309(5) yes C12 . C17 . 1.521(4) yes C13 . C140 . 1.543(12) yes C13 . C141 . 1.511(8) yes C13 . H131 . 1.000 no C17 . C18 . 1.542(4) yes C17 . C30 . 1.521(4) yes C17 . H171 . 1.000 no C18 . H181 . 1.000 no C18 . H182 . 1.000 no C23 . C24 . 1.385(5) yes C23 . C29 . 1.389(5) yes C24 . C25 . 1.384(5) yes C24 . H241 . 1.000 no C25 . C26 . 1.398(5) yes C25 . H251 . 1.000 no C26 . C27 . 1.498(5) yes C26 . C28 . 1.390(5) yes C27 . H271 . 1.000 no C27 . H272 . 1.000 no C27 . H273 . 1.000 no C28 . C29 . 1.384(4) yes C28 . H281 . 1.000 no C29 . H291 . 1.000 no C30 . C31 . 1.398(4) yes C30 . C38 . 1.389(4) yes C31 . C32 . 1.376(4) yes C31 . H311 . 1.000 no C32 . C36 . 1.380(4) yes C34 . H341 . 1.000 no C34 . H342 . 1.000 no C36 . C37 . 1.370(4) yes C37 . C38 . 1.398(4) yes C37 . H371 . 1.000 no C38 . H381 . 1.000 no C140 . C141 . 0.360(19) yes C140 . C150 . 1.544(13) yes C140 . C151 . 1.686(17) yes C140 . H140 . 1.000 no C140 . H141 . 1.000 no C140 . H142 . 1.248(16) no C140 . H143 . 0.683(16) no C141 . C150 . 1.665(15) yes C141 . C151 . 1.519(8) yes C141 . H140 . 0.746(15) no C141 . H142 . 1.000 no C141 . H143 . 1.000 no C150 . C151 . 1.289(13) yes C150 . C160 . 1.529(14) yes C150 . C161 . 1.300(14) yes C150 . H163 . 1.120(14) no C150 . H150 . 1.000 no C150 . H151 . 1.000 no C151 . C160 . 1.370(15) yes C151 . C161 . 1.530(8) yes C151 . H160 . 1.174(13) no C151 . H152 . 1.000 no C151 . H153 . 1.000 no C160 . C161 . 0.446(15) yes C160 . H160 . 1.000 no C160 . H161 . 1.000 no C160 . H162 . 1.023(14) no C161 . H161 . 0.952(13) no C161 . H162 . 1.000 no C161 . H163 . 1.000 no H161 . H162 . 0.099(14) no H140 . H142 . 0.494(18) no H141 . H143 . 0.555(19) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O21 . S20 . O22 . 119.73(15) yes O21 . S20 . N19 . 106.13(14) yes O22 . S20 . N19 . 107.00(14) yes O21 . S20 . C23 . 107.55(15) yes O22 . S20 . C23 . 107.25(15) yes N19 . S20 . C23 . 108.84(13) yes C1 . O4 . C11 . 116.2(3) yes C32 . O33 . C34 . 104.8(2) yes C34 . O35 . C36 . 104.6(2) yes S20 . N19 . C18 . 119.9(2) yes S20 . N19 . H1 . 109.6(1) no C18 . N19 . H1 . 111.55(16) no O3 . C1 . O4 . 123.0(3) yes O3 . C1 . C2 . 125.3(4) yes O4 . C1 . C2 . 111.7(3) yes C1 . C2 . H21 . 109.8(2) no C1 . C2 . H22 . 109.1(2) no H21 . C2 . H22 . 109.475 no C1 . C2 . H23 . 109.5(2) no H21 . C2 . H23 . 109.476 no H22 . C2 . H23 . 109.476 no O4 . C11 . C12 . 106.5(2) yes O4 . C11 . C160 . 119.8(6) yes C12 . C11 . C160 . 111.9(6) yes O4 . C11 . C161 . 104.5(3) yes C12 . C11 . C161 . 113.9(3) yes C160 . C11 . C161 . 16.7(6) yes O4 . C11 . H111 . 112.63(17) no C12 . C11 . H111 . 107.72(18) no C160 . C11 . H111 . 97.7(4) no C161 . C11 . H111 . 111.5(3) no C11 . C12 . C13 . 121.1(3) yes C11 . C12 . C17 . 114.8(3) yes C13 . C12 . C17 . 123.9(3) yes C12 . C13 . C140 . 124.4(5) yes C12 . C13 . C141 . 125.6(4) yes C140 . C13 . C141 . 13.5(7) yes C12 . C13 . H131 . 116.6(2) no C140 . C13 . H131 . 117.5(4) no C141 . C13 . H131 . 117.8(3) no C12 . C17 . C18 . 107.5(2) yes C12 . C17 . C30 . 112.4(2) yes C18 . C17 . C30 . 114.2(2) yes C12 . C17 . H171 . 111.97(16) no C18 . C17 . H171 . 108.03(15) no C30 . C17 . H171 . 102.78(15) no N19 . C18 . C17 . 113.1(2) yes N19 . C18 . H181 . 108.41(14) no C17 . C18 . H181 . 108.49(15) no N19 . C18 . H182 . 109.34(16) no C17 . C18 . H182 . 108.01(15) no H181 . C18 . H182 . 109.468 no S20 . C23 . C24 . 121.1(2) yes S20 . C23 . C29 . 118.6(2) yes C24 . C23 . C29 . 120.3(3) yes C23 . C24 . C25 . 119.8(3) yes C23 . C24 . H241 . 120.03(18) no C25 . C24 . H241 . 120.1(2) no C24 . C25 . C26 . 120.8(3) yes C24 . C25 . H251 . 119.9(2) no C26 . C25 . H251 . 119.36(18) no C25 . C26 . C27 . 120.4(3) yes C25 . C26 . C28 . 118.4(3) yes C27 . C26 . C28 . 121.2(3) yes C26 . C27 . H271 . 108.5(2) no C26 . C27 . H272 . 109.9(2) no H271 . C27 . H272 . 109.476 no C26 . C27 . H273 . 110.0(2) no H271 . C27 . H273 . 109.476 no H272 . C27 . H273 . 109.476 no C26 . C28 . C29 . 121.3(3) yes C26 . C28 . H281 . 119.22(19) no C29 . C28 . H281 . 119.47(19) no C23 . C29 . C28 . 119.4(3) yes C23 . C29 . H291 . 120.02(18) no C28 . C29 . H291 . 120.61(19) no C17 . C30 . C31 . 122.8(2) yes C17 . C30 . C38 . 117.7(3) yes C31 . C30 . C38 . 119.5(3) yes C30 . C31 . C32 . 117.4(3) yes C30 . C31 . H311 . 121.27(16) no C32 . C31 . H311 . 121.36(17) no O33 . C32 . C31 . 127.6(3) yes O33 . C32 . C36 . 110.0(2) yes C31 . C32 . C36 . 122.3(3) yes O33 . C34 . O35 . 107.7(2) yes O33 . C34 . H341 . 110.48(19) no O35 . C34 . H341 . 109.93(18) no O33 . C34 . H342 . 109.65(18) no O35 . C34 . H342 . 109.56(18) no H341 . C34 . H342 . 109.466 no O35 . C36 . C32 . 109.4(3) yes O35 . C36 . C37 . 128.9(3) yes C32 . C36 . C37 . 121.7(3) yes C36 . C37 . C38 . 116.3(3) yes C36 . C37 . H371 . 121.44(17) no C38 . C37 . H371 . 122.27(17) no C30 . C38 . C37 . 122.9(3) yes C30 . C38 . H381 . 118.17(17) no C37 . C38 . H381 . 118.98(17) no C13 . C140 . C141 . 78.2(26) yes C13 . C140 . C150 . 109.6(2) yes C141 . C140 . C150 . 103.4(31) yes C13 . C140 . C151 . 100.0(7) yes C141 . C140 . C151 . 56.7(28) yes C150 . C140 . C151 . 46.8(6) yes C13 . C140 . H140 . 109.9(6) no C141 . C140 . H140 . 37.4(17) no C150 . C140 . H140 . 109.5(7) no C151 . C140 . H140 . 70.5(5) no C13 . C140 . H141 . 109.0(6) no C141 . C140 . H141 . 140.9(19) no C150 . C140 . H141 . 109.4(6) no C151 . C140 . H141 . 148.4(5) no H140 . C140 . H141 . 109.467 no C13 . C140 . H142 . 94.9(10) no C141 . C140 . H142 . 40.2(14) no C150 . C140 . H142 . 131.1(15) no C151 . C140 . H142 . 88.6(11) no H140 . C140 . H142 . 22.1(9) no C13 . C140 . H143 . 133.8(22) no C141 . C140 . H143 . 145.2(32) no C150 . C140 . H143 . 80.5(16) no C151 . C140 . H143 . 116.6(19) no H140 . C140 . H143 . 108.3(12) no H141 . C140 . H142 . 100.9(7) no H141 . C140 . H143 . 32.0(17) no H142 . C140 . H143 . 112.2(11) no C13 . C141 . C140 . 88.3(27) yes C13 . C141 . C150 . 105.0(5) yes C140 . C141 . C150 . 64.4(27) yes C13 . C141 . C151 . 109.62(19) yes C140 . C141 . C151 . 111.8(30) yes C150 . C141 . C151 . 47.5(5) yes C13 . C141 . H140 . 134.9(16) no C140 . C141 . H140 . 125.6(24) no C150 . C141 . H140 . 115.9(16) no C151 . C141 . H140 . 86.4(15) no C13 . C141 . H142 . 109.0(3) no C140 . C141 . H142 . 126.4(17) no C150 . C141 . H142 . 144.3(5) no C151 . C141 . H142 . 109.1(3) no H140 . C141 . H142 . 28.4(15) no C13 . C141 . H143 . 109.7(3) no C140 . C141 . H143 . 22.9(21) no C150 . C141 . H143 . 67.6(4) no C151 . C141 . H143 . 109.9(3) no H140 . C141 . H143 . 103.1(12) no H142 . C141 . H143 . 109.467 no C140 . C150 . C141 . 12.2(7) yes C140 . C150 . C151 . 72.4(8) yes C141 . C150 . C151 . 60.3(6) yes C140 . C150 . C160 . 109.6(2) yes C141 . C150 . C160 . 100.3(5) yes C151 . C150 . C160 . 57.4(6) yes C140 . C150 . C161 . 121.8(6) yes C141 . C150 . C161 . 113.9(7) yes C151 . C150 . C161 . 72.4(7) yes C160 . C150 . C161 . 15.6(7) yes C140 . C150 . H163 . 143.1(10) no C141 . C150 . H163 . 146.2(10) no C151 . C150 . H163 . 119.8(11) no C160 . C150 . H163 . 63.7(9) no C161 . C150 . H163 . 48.1(6) no C140 . C150 . H150 . 109.5(5) no C141 . C150 . H150 . 106.7(5) no C151 . C150 . H150 . 83.0(6) no C160 . C150 . H150 . 109.6(4) no C161 . C150 . H150 . 110.5(6) no C140 . C150 . H151 . 109.5(7) no C141 . C150 . H151 . 120.9(5) no C151 . C150 . H151 . 165.1(6) no C160 . C150 . H151 . 109.2(5) no C161 . C150 . H151 . 94.9(6) no H163 . C150 . H150 . 106.7(7) no H163 . C150 . H151 . 49.7(7) no H150 . C150 . H151 . 109.467 no C140 . C151 . C141 . 11.4(6) yes C140 . C151 . C150 . 60.8(7) yes C141 . C151 . C150 . 72.2(7) yes C140 . C151 . C160 . 110.1(7) yes C141 . C151 . C160 . 116.2(5) yes C150 . C151 . C160 . 70.2(8) yes C140 . C151 . C161 . 101.2(5) yes C141 . C151 . C161 . 109.71(19) yes C150 . C151 . C161 . 54.1(6) yes C160 . C151 . C161 . 16.5(6) yes C140 . C151 . H160 . 134.5(8) no C141 . C151 . H160 . 131.1(7) no C150 . C151 . H160 . 115.7(10) no C160 . C151 . H160 . 45.5(5) no C161 . C151 . H160 . 61.7(8) no C140 . C151 . H152 . 120.8(5) no C141 . C151 . H152 . 109.9(3) no C150 . C151 . H152 . 160.9(6) no C160 . C151 . H152 . 92.8(6) no C161 . C151 . H152 . 109.3(3) no C140 . C151 . H153 . 106.2(4) no C141 . C151 . H153 . 109.2(2) no C150 . C151 . H153 . 86.7(6) no C160 . C151 . H153 . 117.8(6) no C161 . C151 . H153 . 109.2(2) no H160 . C151 . H152 . 48.0(8) no H160 . C151 . H153 . 119.1(6) no H152 . C151 . H153 . 109.467 no C11 . C160 . C150 . 109.3(2) yes C11 . C160 . C151 . 125.3(9) yes C150 . C160 . C151 . 52.4(7) yes C11 . C160 . C161 . 91.6(19) yes C150 . C160 . C161 . 51.6(20) yes C151 . C160 . C161 . 102.5(24) yes C11 . C160 . H160 . 110.0(6) no C150 . C160 . H160 . 109.3(5) no C151 . C160 . H160 . 56.9(5) no C161 . C160 . H160 . 156.1(22) no C11 . C160 . H161 . 109.2(5) no C150 . C160 . H161 . 109.5(5) no C151 . C160 . H161 . 125.4(5) no C161 . C160 . H161 . 70.8(17) no H160 . C160 . H161 . 109.467 no C11 . C160 . H162 . 113.7(13) no C150 . C160 . H162 . 109.9(12) no C151 . C160 . H162 . 121.0(12) no C161 . C160 . H162 . 74.4(19) no H160 . C160 . H162 . 104.5(8) no H161 . C160 . H162 . 5.5(8) no C11 . C161 . C150 . 118.1(7) yes C11 . C161 . C151 . 110.08(19) yes C150 . C161 . C151 . 53.4(6) yes C11 . C161 . C160 . 71.7(19) yes C150 . C161 . C160 . 112.8(24) yes C151 . C161 . C160 . 60.9(22) yes C11 . C161 . H161 . 106.3(11) no C150 . C161 . H161 . 135.5(13) no C151 . C161 . H161 . 114.7(11) no C160 . C161 . H161 . 82.9(16) no C11 . C161 . H162 . 109.2(3) no C150 . C161 . H162 . 132.6(6) no C151 . C161 . H162 . 109.6(2) no C160 . C161 . H162 . 80.2(17) no H161 . C161 . H162 . 5.1(10) no C11 . C161 . H163 . 109.2(3) no C150 . C161 . H163 . 56.5(6) no C151 . C161 . H163 . 109.2(3) no C160 . C161 . H163 . 168.7(20) no H161 . C161 . H163 . 107.2(9) no H162 . C161 . H163 . 109.467 no C151 . H160 . C160 . 77.6(7) no C160 . H161 . C161 . 26.3(9) no C160 . H161 . H162 . 100.8(90) no C161 . H161 . H162 . 116.4(99) no C160 . H162 . C161 . 25.5(8) no C160 . H162 . H161 . 73.7(86) no C161 . H162 . H161 . 58.5(91) no C150 . H163 . C161 . 75.4(6) no C140 . H140 . C141 . 17.0(12) no C140 . H140 . H142 . 108.4(21) no C141 . H140 . H142 . 105.6(30) no C140 . H141 . H143 . 40.7(18) no C140 . H142 . C141 . 13.4(7) no C140 . H142 . H140 . 49.5(15) no C141 . H142 . H140 . 46.0(19) no C140 . H143 . C141 . 11.9(13) no C140 . H143 . H141 . 107.4(29) no C141 . H143 . H141 . 110.1(18) no # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_mbkj2z _database_code_CSD 160055 _audit_creation_method 'maXus +CRYSTALS_ver_12-03-99' _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'prism' _exptl_crystal_colour 'Colourless' _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment 'noref' # Submission details _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1994)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 0.03617 _diffrn_orient_matrix_UB_12 0.04793 _diffrn_orient_matrix_UB_13 -0.00380 _diffrn_orient_matrix_UB_21 -0.00518 _diffrn_orient_matrix_UB_22 0.00950 _diffrn_orient_matrix_UB_23 0.07061 _diffrn_orient_matrix_UB_31 0.09036 _diffrn_orient_matrix_UB_32 -0.00383 _diffrn_orient_matrix_UB_33 0.00714 _cell_formula_units_Z 8 _exptl_crystal_density_diffrn 1.36 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 317.50 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,-Y,-Z' '-X+ 1/2,-Y+ 1/2,-Z' '+X+ 1/2,+Y+ 1/2,+Z' '-X,+Y,-Z+ 1/2' '+X,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,+Z+ 1/2' '-X+ 1/2,+Y+ 1/2,-Z+ 1/2' _symmetry_space_group_name_H-M 'C2/c ' _symmetry_cell_setting 'Monoclinic' _chemical_formula_moiety 'C16 H18 N O 2, Cl- , 0.5 (HCl), 0.5 (H2O) ' _chemical_formula_sum 'C16 H 19.5 Cl 1.5 N O 2.5 ' _chemical_name_systematic ; ? ; _cell_length_a 20.0656(2) _cell_length_b 13.9995(2) _cell_length_c 13.3059(2) _cell_angle_alpha 90.00 _cell_angle_beta 124.0651(7) _cell_angle_gamma 90.00 _cell_volume 3096.35(7) _diffrn_reflns_number 39241 _diffrn_reflns_theta_max 30.05 _cell_measurement_reflns_used 20657 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _diffrn_measurement_method 'CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.150 -6 1 -1 0.150 -1 1 1 0.130 1 -1 -1 0.200 1 0 -1 0.190 1 1 -1 0.180 -1 -1 1 0.160 0 0 1 0.160 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.922 _exptl_absorpt_correction_T_max 0.939 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_reflns_av_R_equivalents 0.045 _exptl_absorpt_coefficient_mu 0.339 _exptl_crystal_F_000 1332 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'Cl ' 0.1320 0.1590 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' # Refinement statistics _reflns_d_resolution_low 1.82 _reflns_d_resolution_high 0.60 _reflns_limit_h_min -26 _reflns_limit_h_max 21 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _reflns_number_total 4507 _reflns_number_gt 1851 _refine_ls_number_reflns 1851 _refine_ls_matrix_type full _refine_diff_density_min -0.37 _refine_diff_density_max 0.28 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_parameters 218 _refine_ls_number_restraints 12 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0276 _refine_ls_goodness_of_fit_ref 1.0477 _refine_ls_shift/su_max 0.000310 _refine_ls_structure_factor_coef F _refine_ls_extinction_coef 200.5(243) _refine_ls_extinction_method ; Larson 1970 Crystallographic Computing eq 22 ; _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 4 parameters, Carruthers & Watkin , 1979, 0.279 -.562 0.213E-01-.368 ; loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type Cl1 -0.45707(3) -0.70253(5) 0.12531(5) 0.0536 1.0000 Uani N5 -0.6211(1) -0.64658(11) -0.10733(14) 0.0329 1.0000 Uani O1 -0.52570(16) -0.5789(2) 0.2201(3) 0.0471 0.5000 Uani Cl2 -0.57415(6) -0.44519(7) 0.10401(9) 0.0396 0.5000 Uani O13 -0.82877(9) -0.3668(1) -0.53232(13) 0.0420 1.0000 Uani O15 -0.93680(8) -0.45644(11) -0.56788(14) 0.0457 1.0000 Uani C1 -0.75457(13) -0.80839(14) -0.3496(2) 0.0414 1.0000 Uani C2 -0.70517(14) -0.86579(16) -0.3808(2) 0.0491 1.0000 Uani C3 -0.61441(15) -0.85599(15) -0.2896(2) 0.0496 1.0000 Uani C4 -0.58935(13) -0.75584(15) -0.2337(2) 0.0425 1.0000 Uani C6 -0.6277(1) -0.55842(13) -0.17603(16) 0.0328 1.0000 Uani C7 -0.7247(1) -0.45761(12) -0.35348(16) 0.0312 1.0000 Uani C8 -0.80197(11) -0.43920(13) -0.44763(16) 0.0321 1.0000 Uani C9 -0.86652(11) -0.49308(14) -0.46914(17) 0.0340 1.0000 Uani C10 -0.85725(11) -0.56868(13) -0.39667(17) 0.0345 1.0000 Uani C11 -0.75933(11) -0.67583(14) -0.21875(17) 0.0339 1.0000 Uani C12 -0.68926(12) -0.64944(14) -0.09028(17) 0.0364 1.0000 Uani C14 -0.91113(13) -0.39064(16) -0.62240(19) 0.0450 1.0000 Uani C41 -0.63119(12) -0.74160(13) -0.16925(17) 0.0347 1.0000 Uani C61 -0.7132(1) -0.53594(13) -0.27929(16) 0.0293 1.0000 Uani C101 -0.7780(1) -0.58996(13) -0.29971(16) 0.0300 1.0000 Uani C111 -0.72068(12) -0.75133(13) -0.25357(18) 0.0342 1.0000 Uani H11 -0.81454(13) -0.81364(14) -0.4026(2) 0.051(7) 1.0000 Uiso H21 -0.71984(14) -0.93466(16) -0.3853(2) 0.061(7) 1.0000 Uiso H22 -0.71892(14) -0.84421(16) -0.4620(2) 0.058(7) 1.0000 Uiso H31 -0.59647(15) -0.90368(15) -0.2231(2) 0.072(9) 1.0000 Uiso H32 -0.58738(15) -0.86969(15) -0.3323(2) 0.069(8) 1.0000 Uiso H41 -0.60710(13) -0.70639(15) -0.2982(2) 0.034(6) 1.0000 Uiso H42 -0.52966(13) -0.75225(15) -0.1747(2) 0.059(7) 1.0000 Uiso H51 -0.5656(1) -0.64075(11) -0.03220(14) 0.051(7) 1.0000 Uiso H61 -0.6060(1) -0.50305(13) -0.11871(16) 0.035(5) 1.0000 Uiso H62 -0.5946(1) -0.56790(13) -0.21016(16) 0.042(6) 1.0000 Uiso H71 -0.6786(1) -0.41756(12) -0.33823(16) 0.038(6) 1.0000 Uiso H101 -0.90424(11) -0.60683(13) -0.41204(17) 0.035(5) 1.0000 Uiso H111 -0.80915(11) -0.69700(14) -0.22510(17) 0.035(6) 1.0000 Uiso H121 -0.68022(12) -0.69915(14) -0.02987(17) 0.045(6) 1.0000 Uiso H122 -0.69797(12) -0.58601(14) -0.06483(17) 0.038(6) 1.0000 Uiso H141 -0.94505(13) -0.33167(16) -0.64915(19) 0.051(6) 1.0000 Uiso H142 -0.91571(13) -0.42122(16) -0.69395(19) 0.034(5) 1.0000 Uiso H411 -0.60340(12) -0.79251(13) -0.10611(17) 0.032(5) 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0313(3) 0.0618(4) 0.0527(3) -0.0107(3) 0.0144(2) 0.0065(2) N5 0.0328(7) 0.0339(8) 0.0295(7) 0.0006(6) 0.0159(6) 0.0028(6) O1 0.0392(16) 0.0547(18) 0.0445(19) -0.0054(13) 0.0217(14) 0.0058(12) Cl2 0.0380(5) 0.0409(5) 0.0415(5) -0.0039(4) 0.0232(4) -0.0019(4) O13 0.0411(8) 0.0360(7) 0.0394(7) 0.0066(6) 0.0167(6) 0.0033(6) O15 0.0306(7) 0.0491(8) 0.0424(8) 0.0050(6) 0.0113(6) 0.0075(6) C1 0.0464(12) 0.034(1) 0.0469(11) -0.0074(8) 0.028(1) -0.0084(8) C2 0.0603(14) 0.0389(11) 0.0552(13) -0.015(1) 0.0367(12) -0.010(1) C3 0.0602(14) 0.0395(11) 0.0601(13) -0.003(1) 0.0404(12) 0.007(1) C4 0.0429(11) 0.0425(11) 0.0485(12) -0.0065(9) 0.030(1) -0.0007(9) C6 0.0284(9) 0.0315(9) 0.0337(9) -0.0011(7) 0.0144(8) -0.0010(7) C7 0.0301(8) 0.0291(8) 0.0329(9) -0.0016(7) 0.0167(7) -0.0025(7) C8 0.0365(9) 0.0288(8) 0.0298(8) -0.0016(7) 0.0180(7) 0.0027(7) C9 0.0275(9) 0.0371(9) 0.0326(9) -0.0025(7) 0.0138(8) 0.0045(7) C10 0.0289(9) 0.0351(9) 0.0389(9) -0.0053(8) 0.0185(8) -0.0032(7) C11 0.0371(9) 0.0336(9) 0.037(1) -0.0005(8) 0.0247(8) -0.0026(8) C12 0.043(1) 0.039(1) 0.0327(9) -0.0014(8) 0.0242(8) -0.0002(8) C14 0.0432(11) 0.042(1) 0.037(1) 0.0029(9) 0.0145(9) 0.0084(9) C41 0.040(1) 0.0301(9) 0.0336(9) 0.0005(7) 0.0203(8) 0.0037(7) C61 0.0276(8) 0.0294(8) 0.0292(8) -0.0026(7) 0.0149(7) -0.0008(7) C101 0.0290(8) 0.0308(8) 0.0315(9) -0.0025(7) 0.0178(7) -0.0007(7) C111 0.040(1) 0.0297(8) 0.040(1) 0.0015(7) 0.0266(9) -0.0011(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N5 . C6 . 1.497(2) yes N5 . C12 . 1.507(2) yes N5 . C41 . 1.517(2) yes N5 . H51 . 1.000 no O1 . O1 5_455 0.882(5) yes O13 . C8 . 1.381(2) yes O13 . C14 . 1.435(3) yes O15 . C9 . 1.379(2) yes O15 . C14 . 1.435(3) yes C1 . C2 . 1.504(3) yes C1 . C111 . 1.327(3) yes C1 . H11 . 1.000 no C2 . C3 . 1.527(3) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . C4 . 1.534(3) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . C41 . 1.512(3) yes C4 . H41 . 1.000 no C4 . H42 . 1.000 no C6 . C61 . 1.513(2) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C8 . 1.365(3) yes C7 . C61 . 1.405(2) yes C7 . H71 . 1.000 no C8 . C9 . 1.383(3) yes C9 . C10 . 1.373(3) yes C10 . C101 . 1.408(2) yes C10 . H101 . 1.000 no C11 . C12 . 1.531(3) yes C11 . C101 . 1.514(3) yes C11 . C111 . 1.528(3) yes C11 . H111 . 1.000 no C12 . H121 . 1.000 no C12 . H122 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C41 . C111 . 1.498(3) yes C41 . H411 . 1.000 no C61 . C101 . 1.394(2) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C6 . N5 . C12 . 109.68(14) yes C6 . N5 . C41 . 116.86(14) yes C12 . N5 . C41 . 101.66(14) yes C6 . N5 . H51 . 102.16(9) no C12 . N5 . H51 . 116.68(9) no C41 . N5 . H51 . 110.45(9) no C8 . O13 . C14 . 104.56(15) yes C9 . O15 . C14 . 104.80(15) yes C2 . C1 . C111 . 121.75(19) yes C2 . C1 . H11 . 118.98(12) no C111 . C1 . H11 . 119.27(13) no C1 . C2 . C3 . 114.15(18) yes C1 . C2 . H21 . 108.28(11) no C3 . C2 . H21 . 108.31(12) no C1 . C2 . H22 . 108.12(13) no C3 . C2 . H22 . 108.45(13) no H21 . C2 . H22 . 109.466 no C2 . C3 . C4 . 112.88(17) yes C2 . C3 . H31 . 108.75(13) no C4 . C3 . H31 . 108.91(13) no C2 . C3 . H32 . 108.39(12) no C4 . C3 . H32 . 108.41(11) no H31 . C3 . H32 . 109.467 no C3 . C4 . C41 . 105.06(16) yes C3 . C4 . H41 . 110.76(13) no C41 . C4 . H41 . 110.56(11) no C3 . C4 . H42 . 110.48(12) no C41 . C4 . H42 . 110.45(11) no H41 . C4 . H42 . 109.467 no N5 . C6 . C61 . 113.15(14) yes N5 . C6 . H61 . 108.75(9) no C61 . C6 . H61 . 108.6(1) no N5 . C6 . H62 . 108.28(9) no C61 . C6 . H62 . 108.5(1) no H61 . C6 . H62 . 109.467 no C8 . C7 . C61 . 116.58(16) yes C8 . C7 . H71 . 121.73(11) no C61 . C7 . H71 . 121.7(1) no O13 . C8 . C7 . 127.63(17) yes O13 . C8 . C9 . 109.85(16) yes C7 . C8 . C9 . 122.51(17) yes O15 . C9 . C8 . 109.48(17) yes O15 . C9 . C10 . 128.31(17) yes C8 . C9 . C10 . 122.17(17) yes C9 . C10 . C101 . 116.48(16) yes C9 . C10 . H101 . 121.80(11) no C101 . C10 . H101 . 121.72(11) no C12 . C11 . C101 . 108.03(15) yes C12 . C11 . C111 . 101.59(15) yes C101 . C11 . C111 . 107.39(15) yes C12 . C11 . H111 . 114.5(1) no C101 . C11 . H111 . 109.7(1) no C111 . C11 . H111 . 115.0(1) no N5 . C12 . C11 . 100.46(14) yes N5 . C12 . H121 . 111.6(1) no C11 . C12 . H121 . 111.7(1) no N5 . C12 . H122 . 111.9(1) no C11 . C12 . H122 . 111.5(1) no H121 . C12 . H122 . 109.466 no O13 . C14 . O15 . 107.35(16) yes O13 . C14 . H141 . 110.0(1) no O15 . C14 . H141 . 110.15(11) no O13 . C14 . H142 . 110.08(11) no O15 . C14 . H142 . 109.81(11) no H141 . C14 . H142 . 109.467 no N5 . C41 . C4 . 118.42(16) yes N5 . C41 . C111 . 103.04(14) yes C4 . C41 . C111 . 112.12(16) yes N5 . C41 . H411 . 109.06(9) no C4 . C41 . H411 . 99.03(11) no C111 . C41 . H411 . 115.8(1) no C6 . C61 . C7 . 117.19(15) yes C6 . C61 . C101 . 121.60(16) yes C7 . C61 . C101 . 121.20(16) yes C10 . C101 . C11 . 121.49(16) yes C10 . C101 . C61 . 121.03(17) yes C11 . C101 . C61 . 117.37(16) yes C1 . C111 . C11 . 129.43(19) yes C1 . C111 . C41 . 121.92(18) yes C11 . C111 . C41 . 108.00(16) yes #Crystal Structure Report data_CRYSTALS_cif 160056 _database_code_CSD _audit_creation_method 'maXus + CRYSTALS_ver_12-03-99' _chemical_compound_source 'Local laboratory' _exptl_crystal_description 'square plate' _exptl_crystal_colour 'yellow' _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment 'mixed' # Submission details _diffrn_measurement_device 'KappaCCD' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 -0.06663 _diffrn_orient_matrix_UB_12 -0.05975 _diffrn_orient_matrix_UB_13 0.00949 _diffrn_orient_matrix_UB_21 0.06269 _diffrn_orient_matrix_UB_22 -0.01971 _diffrn_orient_matrix_UB_23 0.06861 _diffrn_orient_matrix_UB_31 -0.04266 _diffrn_orient_matrix_UB_32 0.06435 _diffrn_orient_matrix_UB_33 0.02983 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ; _chemical_formula_weight 319.313 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,-Y,-Z' '-X+ 1/2,+Y+ 1/2,-Z+ 1/2' '+X+ 1/2,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_cell_setting 'Monoclinic' _chemical_formula_moiety 'C15 H13 N O5 + C H4 O ' _chemical_formula_sum 'C16 H17 N O6 ' _chemical_name_systematic ; ? ; _cell_length_a 10.4370(6) _cell_length_b 11.1112(6) _cell_length_c 13.9707(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.346(3) _cell_angle_gamma 90.00 _cell_volume 1537.80(14) _diffrn_reflns_number 14104 _diffrn_reflns_theta_max 23.00 _cell_measurement_reflns_used 9591 _cell_measurement_theta_min 2.546 _cell_measurement_theta_max 22.986 _diffrn_measurement_method 'CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom difmap' # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 -1 0.010 -1 0 1 0.040 0 0 1 0.120 0 0 -1 0.110 0 -1 0 0.120 0 1 0 0.120 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _diffrn_reflns_av_R_equivalents 0.061 _exptl_absorpt_coefficient_mu 0.11 _exptl_crystal_F_000 672 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' # Refinement statistics _reflns_d_resolution_low 1.90 _reflns_d_resolution_high 0.67 _reflns_limit_h_min -11 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _refine_ls_matrix_type full _reflns_number_total 2127 _reflns_number_gt 1743 _refine_diff_density_min -0.19 _refine_diff_density_max 0.37 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 1743 _refine_ls_number_parameters 220 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.0450 _refine_ls_goodness_of_fit_ref 1.0581 _refine_ls_shift/su_max 0.000236 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 0.449 0.343 0.197 ; _refine_ls_extinction_coef 96.0(172) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) maxus(Mackay et al., 1999) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 0.59944(15) -0.04641(13) 0.10829(11) 0.0427 1.0000 Uani O9 0.80964(16) 0.19932(14) 0.11608(12) 0.0494 1.0000 Uani O10 0.44507(19) 0.12907(17) 0.34936(14) 0.0643 1.0000 Uani O14 0.29579(17) 0.40271(14) -0.04218(12) 0.0513 1.0000 Uani O16 0.35416(16) 0.57022(13) 0.06082(13) 0.0490 1.0000 Uani O20 0.4793(2) 0.2727(2) 0.51198(16) 0.0765 1.0000 Uani N1 0.74834(19) 0.08703(17) 0.08480(14) 0.0437 1.0000 Uani C2 0.6632(2) 0.06546(19) 0.13033(15) 0.0355 1.0000 Uani C3 0.6156(2) 0.13341(18) 0.20675(15) 0.0337 1.0000 Uani C4 0.4391(2) 0.0442(2) 0.29194(18) 0.0457 1.0000 Uani C5 0.3535(3) -0.0652(3) 0.2913(2) 0.0650 1.0000 Uani C6 0.3188(3) -0.1399(3) 0.1980(3) 0.0786 1.0000 Uani C7 0.4363(3) -0.1671(2) 0.1602(2) 0.0538 1.0000 Uani C11 0.5509(2) 0.25452(18) 0.16958(15) 0.0331 1.0000 Uani C12 0.4517(2) 0.26215(18) 0.07487(15) 0.0342 1.0000 Uani C13 0.3939(2) 0.37264(19) 0.04661(15) 0.0344 1.0000 Uani C15 0.2632(2) 0.5261(2) -0.03120(18) 0.0485 1.0000 Uani C17 0.4284(2) 0.47207(18) 0.10735(16) 0.0361 1.0000 Uani C18 0.5241(2) 0.46699(19) 0.20068(17) 0.0422 1.0000 Uani C19 0.5849(2) 0.35510(19) 0.23054(17) 0.0395 1.0000 Uani C21 0.5932(4) 0.3458(3) 0.5265(3) 0.0905 1.0000 Uani C31 0.5185(2) 0.04081(18) 0.22407(15) 0.0347 1.0000 Uani C71 0.5153(2) -0.05575(19) 0.16633(16) 0.0392 1.0000 Uani H31 0.6889(2) 0.15918(18) 0.26871(15) 0.042(6) 1.0000 Uiso H51 0.4045(3) -0.1179(3) 0.3486(2) 0.113(9) 1.0000 Uiso H52 0.2679(3) -0.0376(3) 0.3021(2) 0.113(9) 1.0000 Uiso H61 0.2783(3) -0.2175(3) 0.2105(3) 0.12(1) 1.0000 Uiso H62 0.2506(3) -0.0941(3) 0.1437(3) 0.12(1) 1.0000 Uiso H71 0.4940(3) -0.2306(2) 0.2038(2) 0.082(7) 1.0000 Uiso H72 0.4037(3) -0.1958(2) 0.0887(2) 0.082(7) 1.0000 Uiso H91 0.87335(16) 0.20855(14) 0.06900(12) 0.107(11) 1.0000 Uiso H121 0.4249(2) 0.19036(18) 0.02981(15) 0.052(7) 1.0000 Uiso H151 0.2725(2) 0.5743(2) -0.08909(18) 0.060(5) 1.0000 Uiso H152 0.1683(2) 0.5320(2) -0.02944(18) 0.060(5) 1.0000 Uiso H181 0.5486(2) 0.53957(19) 0.24503(17) 0.042(6) 1.0000 Uiso H191 0.6557(2) 0.34715(19) 0.29782(17) 0.051(6) 1.0000 Uiso H201 0.4606(2) 0.2170(2) 0.45536(16) 0.130(15) 1.0000 Uiso H211 0.5994(4) 0.3899(3) 0.5957(3) 0.174(12) 1.0000 Uiso H212 0.6816(4) 0.3071(3) 0.5603(3) 0.174(12) 1.0000 Uiso H213 0.5732(4) 0.3996(3) 0.4676(3) 0.174(12) 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0545(9) 0.0301(8) 0.0459(9) -0.0041(7) 0.0192(8) 0.0004(7) O9 0.0478(9) 0.042(1) 0.0616(11) 0.0056(8) 0.0218(8) -0.0007(8) O10 0.0751(12) 0.0652(12) 0.0636(11) -0.011(1) 0.037(1) 0.003(1) O14 0.062(1) 0.0342(9) 0.044(1) -0.0014(7) -0.0025(8) 0.0084(8) O16 0.053(1) 0.0278(9) 0.058(1) -0.0012(7) 0.0069(8) 0.0058(7) O20 0.0639(12) 0.1002(16) 0.0742(13) -0.0318(12) 0.034(1) -0.0058(12) N1 0.0457(11) 0.0396(11) 0.0465(11) 0.0074(9) 0.0157(9) 0.0074(9) C2 0.0369(11) 0.0325(12) 0.0355(12) 0.0043(9) 0.009(1) 0.0067(9) C3 0.0368(11) 0.0291(11) 0.0333(11) -0.0003(9) 0.0083(9) -0.0012(9) C4 0.0470(13) 0.0465(14) 0.0457(14) 0.0062(12) 0.0176(11) 0.0075(11) C5 0.0650(17) 0.0617(18) 0.0784(19) 0.0081(15) 0.0367(15) -0.0105(15) C6 0.079(2) 0.070(2) 0.091(2) -0.0070(18) 0.0346(18) -0.0340(17) C7 0.0663(16) 0.0343(13) 0.0563(16) 0.0029(11) 0.0129(13) -0.0103(12) C11 0.0337(11) 0.0294(11) 0.0374(12) -0.0011(9) 0.013(1) -0.0007(9) C12 0.0382(12) 0.0272(11) 0.0351(12) -0.0052(9) 0.008(1) -0.0010(9) C13 0.0342(11) 0.0338(12) 0.0329(11) -0.001(1) 0.0075(9) 0.0002(9) C15 0.0533(14) 0.0346(13) 0.0515(15) 0.0013(11) 0.0077(12) 0.0078(11) C17 0.0368(12) 0.0257(12) 0.0475(13) -0.002(1) 0.016(1) -0.0011(9) C18 0.0450(13) 0.0291(12) 0.0474(14) -0.0126(11) 0.0072(11) -0.003(1) C19 0.0400(12) 0.0345(13) 0.0401(12) -0.006(1) 0.007(1) -0.003(1) C21 0.082(2) 0.077(2) 0.126(3) -0.004(2) 0.052(2) -0.0088(19) C31 0.0371(11) 0.0306(12) 0.0352(11) 0.004(1) 0.0097(9) 0.0039(9) C71 0.0424(12) 0.0337(12) 0.0395(12) 0.006(1) 0.010(1) 0.003(1) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.398(3) yes O1 . C71 . 1.374(3) yes O9 . N1 . 1.408(2) yes O9 . H91 . 1.077 no O10 . C4 . 1.227(3) yes O14 . C13 . 1.378(3) yes O14 . C15 . 1.432(3) yes O16 . C15 . 1.424(3) yes O16 . C17 . 1.377(3) yes O20 . C21 . 1.401(4) yes O20 . H201 . 0.974 no N1 . C2 . 1.268(3) yes C2 . C3 . 1.513(3) yes C3 . C11 . 1.522(3) yes C3 . C31 . 1.516(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.507(3) yes C4 . C31 . 1.443(3) yes C5 . C6 . 1.491(4) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C6 . C7 . 1.511(4) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C71 . 1.475(3) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C11 . C12 . 1.403(3) yes C11 . C19 . 1.382(3) yes C12 . C13 . 1.370(3) yes C12 . H121 . 1.000 no C13 . C17 . 1.370(3) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no C17 . C18 . 1.371(3) yes C18 . C19 . 1.399(3) yes C18 . H181 . 1.000 no C19 . H191 . 1.000 no C21 . H211 . 1.068 no C21 . H212 . 0.992 no C21 . H213 . 0.986 no C31 . C71 . 1.336(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . O1 . C71 . 106.58(16) yes N1 . O9 . H91 . 101.7(1) no C13 . O14 . C15 . 105.66(16) yes C15 . O16 . C17 . 105.66(16) yes C21 . O20 . H201 . 115.45(17) no O9 . N1 . C2 . 109.49(18) yes O1 . C2 . N1 . 114.68(19) yes O1 . C2 . C3 . 111.11(17) yes N1 . C2 . C3 . 134.2(2) yes C2 . C3 . C11 . 114.17(17) yes C2 . C3 . C31 . 99.11(16) yes C11 . C3 . C31 . 114.04(17) yes C2 . C3 . H31 . 114.96(11) no C11 . C3 . H31 . 100.30(11) no C31 . C3 . H31 . 115.08(11) no O10 . C4 . C5 . 122.2(2) yes O10 . C4 . C31 . 121.9(2) yes C5 . C4 . C31 . 115.9(2) yes C4 . C5 . C6 . 115.8(2) yes C4 . C5 . H51 . 107.64(14) no C6 . C5 . H51 . 107.20(18) no C4 . C5 . H52 . 107.93(14) no C6 . C5 . H52 . 108.69(17) no H51 . C5 . H52 . 109.466 no C5 . C6 . C7 . 114.6(2) yes C5 . C6 . H61 . 109.08(15) no C7 . C6 . H61 . 108.81(15) no C5 . C6 . H62 . 107.36(19) no C7 . C6 . H62 . 107.42(17) no H61 . C6 . H62 . 109.467 no C6 . C7 . C71 . 108.2(2) yes C6 . C7 . H71 . 109.15(17) no C71 . C7 . H71 . 109.76(13) no C6 . C7 . H72 . 110.74(16) no C71 . C7 . H72 . 109.52(14) no H71 . C7 . H72 . 109.467 no C3 . C11 . C12 . 119.47(18) yes C3 . C11 . C19 . 120.28(18) yes C12 . C11 . C19 . 120.18(19) yes C11 . C12 . C13 . 116.96(18) yes C11 . C12 . H121 . 121.51(12) no C13 . C12 . H121 . 121.53(12) no O14 . C13 . C12 . 127.71(19) yes O14 . C13 . C17 . 109.76(18) yes C12 . C13 . C17 . 122.53(19) yes O14 . C15 . O16 . 108.24(17) yes O14 . C15 . H151 . 109.83(12) no O16 . C15 . H151 . 109.80(12) no O14 . C15 . H152 . 109.65(12) no O16 . C15 . H152 . 109.84(12) no H151 . C15 . H152 . 109.467 no O16 . C17 . C13 . 110.30(18) yes O16 . C17 . C18 . 127.93(19) yes C13 . C17 . C18 . 121.8(2) yes C17 . C18 . C19 . 116.53(19) yes C17 . C18 . H181 . 121.57(12) no C19 . C18 . H181 . 121.90(12) no C11 . C19 . C18 . 122.0(2) yes C11 . C19 . H191 . 118.58(12) no C18 . C19 . H191 . 119.39(12) no O20 . C21 . H211 . 101.82(17) no O20 . C21 . H212 . 115.97(18) no H211 . C21 . H212 . 89.186 no O20 . C21 . H213 . 106.5(2) no H211 . C21 . H213 . 114.479 no H212 . C21 . H213 . 125.479 no C3 . C31 . C4 . 129.65(19) yes C3 . C31 . C71 . 109.82(18) yes C4 . C31 . C71 . 120.5(2) yes O1 . C71 . C7 . 118.6(2) yes O1 . C71 . C31 . 113.38(19) yes C7 . C71 . C31 . 128.0(2) yes