# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_CRYSTALS_cif_ES27 _database_code_CSD 184753 _journal_coden_Cambridge 207 _audit_creation_date 01-15-06 _audit_creation_method CRYSTALS_ver_12-03-99 # ES27 # Check this file using the IUCr facility at: # http://www/iucr.ac.uk/iucr-top/journals/acta/c/services/checkcif.html #**************************************************************************** # The contents of this file between this point and the next #***** line # are held in the file REFCIF.DAT # This is a character file which you may edit to reflect local conditions # # Items which need looking at are represented by a '?' # Items for which there are choices are prefixed with 'choose from' # # 1. SUBMISSION DETAILS _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper. The figures have been sent by mail. ; _publ_contact_author_name 'Prof Stephen G Davies' _publ_contact_author_address ; Dyson Perrins Laboratory University of Oxford South Parks Road OXFORD OX1 3QY UK ; _publ_contact_author_phone ' 01865 270 826 ' _publ_contact_author_fax ' 01865 272 699 ' _publ_contact_author_email ' STEVE.DAVIES@CHEMISTRY.OX.AC.UK ' _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Davies, Stephen G.' 'Bull, Steven D.' 'Fox, David J.' 'Gianotti, Massimo' 'Kelly, Peter M.' 'Pierres, Camille' 'Savory, Edward D.' 'Smith, Andrew D.' #===================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #********************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et all 2001) ; _computing_publication_material ; CRYSTALS (Watkin et all 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 11.4818(13) _cell_angle_alpha 90 _cell_length_b 12.894(3) _cell_angle_beta 90 _cell_length_c 17.1468(18) _cell_angle_gamma 90 _cell_volume 2538.5 _symmetry_cell_setting 'Orthorhombic ' _symmetry_space_group_name_H-M 'P 21 21 21 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 'x+1/2,-y+1/2,-z' '-x,y+1/2,-z+1/2' '-x+1/2,-y,z+1/2' 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 ' 0.0170 0.0090 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 ' 0.0290 0.0180 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 ' 0.0470 0.0320 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' _chemical_formula_sum ' C28 H34 N2 O3 ' _chemical_formula_moiety ' C28 H34 N2 O3 ' _chemical_compound_source ; ? ; _chemical_formula_weight 446.59 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22 _cell_measurement_theta_max 43 _cell_measurement_temperature 293 _cell_formula_units_Z 4 _exptl_crystal_description ' cubem ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.60 _exptl_crystal_size_mid 0.80 _exptl_crystal_size_max 0.80 _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 962.554 _exptl_absorpt_coefficient_mu 0.598 # Sheldrick geometric definitions 0.62 0.70 _diffrn_measurement_device_type ; Unknown ; _diffrn_radiation_monochromator graphite _computing_data_collection ; DATA COLLECTION ; _computing_data_reduction ; SPARE ; _computing_cell_refinement ; SPARE ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; Azimutal absorption correction (North et al, 1968) ; _exptl_absorpt_correction_T_min 0.69 _exptl_absorpt_correction_T_max 0.70 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 3 _diffrn_standards_decay_% 0.89 _diffrn_ambient_temperature 293 _diffrn_reflns_number 2953 _reflns_number_total 2927 _diffrn_reflns_av_R_equivalents 0.00 # Number of reflections with Friedels Law is 2927 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2585 _diffrn_measured_fraction_theta_max 1.000 _reflns_number_gt 2838 _diffrn_reflns_theta_min 4.29 _diffrn_reflns_theta_max 74.20 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min 0 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _refine_diff_density_min -0.13 _refine_diff_density_max 0.28 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 2838 _refine_ls_number_parameters 299 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.0437 _refine_ls_goodness_of_fit_ref 1.1288 _refine_ls_shift/su_max 0.000196 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 5.13 0.335 3.47 ; _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Spare Spare Spare Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 North, A.C.T., Phillips, D.C. and Mathews, F.S., (1968), Acta Cryst, A24, 351-359 Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # 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 0.4380(1) 0.33632(9) 0.11440(7) 0.0522 1.0000 Uani N2 0.59076(11) 0.1745(1) 0.27133(7) 0.0436 1.0000 Uani O3 0.59697(13) 0.25112(14) 0.07316(8) 0.0726 1.0000 Uani C4 0.67071(13) 0.25029(11) 0.23590(8) 0.0429 1.0000 Uani C5 0.63841(15) 0.06901(12) 0.2763(1) 0.0510 1.0000 Uani C6 0.54650(15) 0.30174(12) 0.12141(9) 0.0480 1.0000 Uani C7 0.75048(16) 0.38416(14) 0.33239(12) 0.0586 1.0000 Uani C8 0.55190(16) 0.01529(13) 0.14853(11) 0.0551 1.0000 Uani C9 0.64656(15) 0.01624(11) 0.1983(1) 0.0496 1.0000 Uani C10 0.76440(13) 0.29336(12) 0.2901(1) 0.0473 1.0000 Uani C11 0.33646(17) 0.17884(17) 0.27250(12) 0.0632 1.0000 Uani C12 0.52679(15) 0.20647(13) 0.34209(9) 0.0492 1.0000 Uani C13 0.35426(17) 0.10097(15) 0.39664(12) 0.0617 1.0000 Uani N14 0.93802(17) 0.36775(17) 0.39227(13) 0.0850 1.0000 Uani C15 0.60068(14) 0.33721(11) 0.19682(9) 0.0469 1.0000 Uani O16 0.06874(13) 0.03936(16) 0.30573(12) 0.0882 1.0000 Uani C17 0.40389(15) 0.16001(13) 0.3383(1) 0.0513 1.0000 Uani C18 0.24056(19) 0.05931(17) 0.38733(13) 0.0689 1.0000 Uani C19 0.86914(16) 0.24166(16) 0.29958(13) 0.0658 1.0000 Uani C20 0.55446(19) -0.03951(15) 0.07870(12) 0.0651 1.0000 Uani C21 0.6529(2) -0.09349(16) 0.05762(12) 0.0707 1.0000 Uani C22 0.3477(2) 0.19818(17) 0.03705(15) 0.0796 1.0000 Uani C23 0.17845(17) 0.07787(16) 0.32157(13) 0.0657 1.0000 Uani C24 0.22499(17) 0.13856(19) 0.26370(13) 0.0700 1.0000 Uani C25 0.8382(2) 0.41798(18) 0.38142(14) 0.0733 1.0000 Uani C26 0.74608(18) -0.03805(16) 0.17535(13) 0.0674 1.0000 Uani C27 0.36568(18) 0.31475(14) 0.04455(11) 0.0627 1.0000 Uani C28 0.7484(2) -0.09226(19) 0.10568(15) 0.0765 1.0000 Uani C29 0.5886(2) 0.18705(17) 0.4195(1) 0.0665 1.0000 Uani C30 0.9515(2) 0.2813(2) 0.35062(18) 0.0859 1.0000 Uani C31 0.2524(2) 0.3679(2) 0.06502(17) 0.0850 1.0000 Uani C32 0.4207(3) 0.3620(2) -0.02632(14) 0.0955 1.0000 Uani C33 0.0253(3) -0.0380(3) 0.3537(2) 0.1138 1.0000 Uani H41 0.7164 0.2089 0.1955 0.0551 1.0000 Uiso H51 0.7178 0.0724 0.3016 0.0649 1.0000 Uiso H52 0.5862 0.0265 0.3121 0.0649 1.0000 Uiso H71 0.6781 0.4275 0.3256 0.0712 1.0000 Uiso H81 0.4794 0.0543 0.1639 0.0693 1.0000 Uiso H111 0.3712 0.2215 0.2293 0.0768 1.0000 Uiso H121 0.5221 0.2843 0.3417 0.0595 1.0000 Uiso H131 0.4018 0.0869 0.4459 0.0797 1.0000 Uiso H151 0.6541 0.3979 0.1854 0.0600 1.0000 Uiso H152 0.5380 0.3617 0.2333 0.0600 1.0000 Uiso H181 0.2041 0.0174 0.4318 0.0825 1.0000 Uiso H191 0.8853 0.1775 0.2675 0.0782 1.0000 Uiso H201 0.4856 -0.0382 0.0420 0.0819 1.0000 Uiso H211 0.6554 -0.1367 0.0078 0.0865 1.0000 Uiso H221 0.2986 0.1805 -0.0092 0.0969 1.0000 Uiso H222 0.4235 0.1600 0.0337 0.0969 1.0000 Uiso H223 0.3049 0.1711 0.0857 0.0969 1.0000 Uiso H241 0.1779 0.1549 0.2155 0.0866 1.0000 Uiso H251 0.8246 0.4836 0.4121 0.0930 1.0000 Uiso H261 0.8155 -0.0402 0.2121 0.0784 1.0000 Uiso H281 0.8224 -0.1288 0.0895 0.0915 1.0000 Uiso H291 0.5413 0.2117 0.4643 0.0832 1.0000 Uiso H292 0.6665 0.2262 0.4205 0.0832 1.0000 Uiso H293 0.6069 0.1114 0.4261 0.0832 1.0000 Uiso H301 1.0260 0.2402 0.3577 0.1002 1.0000 Uiso H311 0.1935 0.3600 0.0223 0.1020 1.0000 Uiso H312 0.2636 0.4439 0.0760 0.1020 1.0000 Uiso H313 0.2181 0.3353 0.1142 0.1020 1.0000 Uiso H321 0.3716 0.3446 -0.0735 0.1101 1.0000 Uiso H322 0.4310 0.4364 -0.0213 0.1101 1.0000 Uiso H323 0.5002 0.3272 -0.0350 0.1101 1.0000 Uiso H331 -0.0540 -0.0614 0.3383 0.1465 1.0000 Uiso H332 0.0223 -0.0146 0.4105 0.1465 1.0000 Uiso H333 0.0789 -0.1020 0.3529 0.1465 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 0.0519(6) 0.0543(6) 0.0505(6) -0.0082(5) -0.0119(5) 0.0106(5) N2 0.0452(6) 0.0387(6) 0.0469(6) 0.0041(5) 0.0016(5) 0.0018(5) O3 0.0659(7) 0.101(1) 0.0514(6) -0.0093(7) 0.0032(6) 0.0232(8) C4 0.0394(6) 0.0418(6) 0.0475(7) 0.0053(6) -0.0029(6) 0.0004(6) C5 0.0554(8) 0.0412(7) 0.0565(8) 0.0083(7) -0.0025(7) 0.0045(7) C6 0.0486(8) 0.0502(7) 0.0453(7) 0.0059(6) 0.0006(6) 0.0039(7) C7 0.0527(9) 0.0547(9) 0.068(1) -0.0023(8) -0.0124(8) 0.0031(8) C8 0.0507(8) 0.0511(8) 0.0635(9) -0.0012(7) 0.0039(8) 0.0022(7) C9 0.0517(8) 0.0378(6) 0.0593(9) 0.0082(6) 0.0061(7) 0.0012(6) C10 0.0401(7) 0.0483(7) 0.0534(8) 0.0063(7) -0.0044(6) -0.0015(6) C11 0.0544(9) 0.0726(11) 0.063(1) 0.0034(9) 0.0053(8) -0.0022(9) C12 0.0543(8) 0.0472(7) 0.0462(7) 0.0007(6) 0.0034(7) -0.0023(7) C13 0.062(1) 0.061(1) 0.062(1) 0.0069(8) 0.0136(9) 0.0012(8) N14 0.067(1) 0.0882(12) 0.0997(14) -0.0098(12) -0.0346(11) 0.0009(9) C15 0.0472(7) 0.0420(7) 0.0514(8) 0.0064(6) -0.0069(7) 0.0004(6) O16 0.0562(8) 0.1046(12) 0.1037(12) 0.011(1) 0.0037(8) -0.0099(8) C17 0.0530(8) 0.0472(7) 0.0536(8) -0.0014(7) 0.0104(7) 0.0023(7) C18 0.0675(11) 0.0685(11) 0.0708(11) 0.010(1) 0.023(1) -0.005(1) C19 0.0469(8) 0.066(1) 0.0841(12) -0.004(1) -0.0116(9) 0.0089(8) C20 0.0718(11) 0.060(1) 0.063(1) -0.0022(8) 0.0000(9) -0.004(1) C21 0.0912(14) 0.0576(9) 0.0633(11) -0.0018(9) 0.0179(11) 0.002(1) C22 0.0872(14) 0.0607(11) 0.0909(14) -0.0222(11) -0.0352(12) 0.0092(11) C23 0.0491(9) 0.065(1) 0.0831(12) -0.003(1) 0.0113(9) 0.0030(8) C24 0.0527(9) 0.0863(14) 0.0710(11) 0.0057(11) 0.0009(9) 0.003(1) C25 0.0701(12) 0.0684(11) 0.0814(13) -0.0111(11) -0.0228(11) -0.002(1) C26 0.059(1) 0.065(1) 0.0784(12) 0.0079(9) 0.0063(9) 0.0168(9) C27 0.0711(11) 0.0564(9) 0.061(1) -0.0130(8) -0.0257(9) 0.0135(9) C28 0.0766(13) 0.0696(12) 0.0831(14) 0.0012(11) 0.0192(12) 0.0219(11) C29 0.0755(11) 0.0772(12) 0.0467(8) 0.0047(9) -0.0017(8) -0.009(1) C30 0.054(1) 0.0934(15) 0.1107(17) -0.0104(14) -0.0302(12) 0.0152(11) C31 0.0682(12) 0.0827(13) 0.1041(17) -0.0324(13) -0.0394(13) 0.0249(11) C32 0.125(2) 0.1022(17) 0.0599(11) 0.0098(12) -0.0257(14) 0.0165(17) C33 0.0830(16) 0.143(3) 0.115(2) 0.014(2) 0.0042(16) -0.0506(19) _refine_ls_extinction_coef 2159.6(573) _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 O1 . C6 . 1.329(2) yes O1 . C27 . 1.483(2) yes N2 . C4 . 1.4719(19) yes N2 . C5 . 1.4687(19) yes N2 . C12 . 1.477(2) yes O3 . C6 . 1.203(2) yes C4 . C10 . 1.526(2) yes C4 . C15 . 1.533(2) yes C4 . H41 . 1.0195(15) no C5 . C9 . 1.504(3) yes C5 . H51 . 1.0104(17) no C5 . H52 . 1.0178(17) no C6 . C15 . 1.506(2) yes C7 . C10 . 1.387(3) yes C7 . C25 . 1.382(3) yes C7 . H71 . 1.0079(18) no C8 . C9 . 1.382(3) yes C8 . C20 . 1.391(3) yes C8 . H81 . 1.0075(17) no C9 . C26 . 1.397(3) yes C10 . C19 . 1.385(2) yes C11 . C17 . 1.390(3) yes C11 . C24 . 1.389(3) yes C11 . H111 . 1.006(2) no C12 . C17 . 1.534(2) yes C12 . C29 . 1.525(2) yes C12 . H121 . 1.0046(16) no C13 . C17 . 1.380(2) yes C13 . C18 . 1.421(3) yes C13 . H131 . 1.022(2) no N14 . C25 . 1.330(3) yes N14 . C30 . 1.332(3) yes C15 . H151 . 1.0134(15) no C15 . H152 . 1.0038(17) no O16 . C23 . 1.381(3) yes O16 . C33 . 1.385(4) yes C18 . C23 . 1.355(3) yes C18 . H181 . 1.0241(19) no C19 . C30 . 1.387(3) yes C19 . H191 . 1.010(2) no C20 . C21 . 1.376(3) yes C20 . H201 . 1.011(2) no C21 . C28 . 1.372(4) yes C21 . H211 . 1.020(2) no C22 . C27 . 1.523(3) yes C22 . H221 . 1.000(2) no C22 . H222 . 1.001(2) no C22 . H223 . 1.029(3) no C23 . C24 . 1.372(3) yes C24 . H241 . 1.010(2) no C25 . H251 . 1.009(2) no C26 . C28 . 1.384(3) yes C26 . H261 . 1.017(2) no C27 . C31 . 1.512(3) yes C27 . C32 . 1.499(4) yes C28 . H281 . 1.010(2) no C29 . H291 . 0.993(2) no C29 . H292 . 1.027(2) no C29 . H293 . 1.004(2) no C30 . H301 . 1.014(2) no C31 . H311 . 1.003(2) no C31 . H312 . 1.006(3) no C31 . H313 . 1.021(3) no C32 . H321 . 1.012(3) no C32 . H322 . 0.970(3) no C32 . H323 . 1.027(3) no C33 . H331 . 0.995(3) no C33 . H332 . 1.021(4) no C33 . H333 . 1.030(4) 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 C6 . O1 . C27 . 122.32(13) yes C4 . N2 . C5 . 113.99(12) yes C4 . N2 . C12 . 117.65(12) yes C5 . N2 . C12 . 113.32(12) yes N2 . C4 . C10 . 115.47(12) yes N2 . C4 . C15 . 109.79(12) yes C10 . C4 . C15 . 111.69(12) yes N2 . C4 . H41 . 104.73(12) no C10 . C4 . H41 . 103.93(12) no C15 . C4 . H41 . 110.83(13) no N2 . C5 . C9 . 112.98(13) yes N2 . C5 . H51 . 108.72(14) no C9 . C5 . H51 . 110.20(15) no N2 . C5 . H52 . 108.33(14) no C9 . C5 . H52 . 109.19(14) no H51 . C5 . H52 . 107.24(15) no O1 . C6 . O3 . 124.86(16) yes O1 . C6 . C15 . 111.29(13) yes O3 . C6 . C15 . 123.81(15) yes C10 . C7 . C25 . 120.04(17) yes C10 . C7 . H71 . 120.16(16) no C25 . C7 . H71 . 119.73(18) no C9 . C8 . C20 . 121.30(17) yes C9 . C8 . H81 . 118.97(17) no C20 . C8 . H81 . 119.73(19) no C5 . C9 . C8 . 120.28(14) yes C5 . C9 . C26 . 121.87(17) yes C8 . C9 . C26 . 117.74(17) yes C4 . C10 . C7 . 122.99(14) yes C4 . C10 . C19 . 120.59(15) yes C7 . C10 . C19 . 116.41(16) yes C17 . C11 . C24 . 122.41(19) yes C17 . C11 . H111 . 118.26(18) no C24 . C11 . H111 . 119.3(2) no N2 . C12 . C17 . 108.29(13) yes N2 . C12 . C29 . 115.94(14) yes C17 . C12 . C29 . 113.60(15) yes N2 . C12 . H121 . 107.43(13) no C17 . C12 . H121 . 109.87(14) no C29 . C12 . H121 . 101.27(14) no C17 . C13 . C18 . 120.44(19) yes C17 . C13 . H131 . 118.42(18) no C18 . C13 . H131 . 121.13(18) no C25 . N14 . C30 . 115.65(18) yes C4 . C15 . C6 . 111.70(13) yes C4 . C15 . H151 . 109.35(13) no C6 . C15 . H151 . 108.60(13) no C4 . C15 . H152 . 109.51(13) no C6 . C15 . H152 . 109.52(14) no H151 . C15 . H152 . 108.09(14) no C23 . O16 . C33 . 118.1(2) yes C11 . C17 . C12 . 118.57(15) yes C11 . C17 . C13 . 117.05(17) yes C12 . C17 . C13 . 124.38(17) yes C13 . C18 . C23 . 120.67(18) yes C13 . C18 . H181 . 119.5(2) no C23 . C18 . H181 . 119.8(2) no C10 . C19 . C30 . 119.30(19) yes C10 . C19 . H191 . 119.28(17) no C30 . C19 . H191 . 121.36(18) no C8 . C20 . C21 . 120.0(2) yes C8 . C20 . H201 . 120.8(2) no C21 . C20 . H201 . 119.2(2) no C20 . C21 . C28 . 119.54(19) yes C20 . C21 . H211 . 121.3(2) no C28 . C21 . H211 . 119.1(2) no C27 . C22 . H221 . 111.6(2) no C27 . C22 . H222 . 111.9(2) no H221 . C22 . H222 . 109.4(2) no C27 . C22 . H223 . 109.3(2) no H221 . C22 . H223 . 107.2(2) no H222 . C22 . H223 . 107.1(2) no O16 . C23 . C18 . 125.5(2) yes O16 . C23 . C24 . 114.7(2) yes C18 . C23 . C24 . 119.83(18) yes C11 . C24 . C23 . 119.6(2) yes C11 . C24 . H241 . 120.2(2) no C23 . C24 . H241 . 120.2(2) no C7 . C25 . N14 . 124.0(2) yes C7 . C25 . H251 . 118.0(2) no N14 . C25 . H251 . 117.97(19) no C9 . C26 . C28 . 120.8(2) yes C9 . C26 . H261 . 118.7(2) no C28 . C26 . H261 . 120.4(2) no O1 . C27 . C22 . 109.22(16) yes O1 . C27 . C31 . 102.05(14) yes C22 . C27 . C31 . 110.5(2) yes O1 . C27 . C32 . 110.04(18) yes C22 . C27 . C32 . 112.9(2) yes C31 . C27 . C32 . 111.5(2) yes C21 . C28 . C26 . 120.57(19) yes C21 . C28 . H281 . 120.1(2) no C26 . C28 . H281 . 119.3(3) no C12 . C29 . H291 . 111.46(19) no C12 . C29 . H292 . 109.86(16) no H291 . C29 . H292 . 107.82(19) no C12 . C29 . H293 . 110.85(17) no H291 . C29 . H293 . 109.69(18) no H292 . C29 . H293 . 107.0(2) no N14 . C30 . C19 . 124.56(19) yes N14 . C30 . H301 . 118.2(2) no C19 . C30 . H301 . 117.2(2) no C27 . C31 . H311 . 111.4(2) no C27 . C31 . H312 . 112.0(2) no H311 . C31 . H312 . 108.8(2) no C27 . C31 . H313 . 109.6(2) no H311 . C31 . H313 . 107.6(3) no H312 . C31 . H313 . 107.3(2) no C27 . C32 . H321 . 108.9(3) no C27 . C32 . H322 . 112.4(2) no H321 . C32 . H322 . 110.9(2) no C27 . C32 . H323 . 108.3(2) no H321 . C32 . H323 . 106.4(3) no H322 . C32 . H323 . 109.6(3) no O16 . C33 . H331 . 113.0(3) no O16 . C33 . H332 . 111.5(3) no H331 . C33 . H332 . 108.2(3) no O16 . C33 . H333 . 110.8(3) no H331 . C33 . H333 . 107.5(3) no H332 . C33 . H333 . 105.5(3) no data_CRYSTALS_cif_es53 _database_code_CSD 184754 _journal_coden_Cambridge 207 _audit_creation_date 02-26-04 _audit_creation_method CRYSTALS_ver_12-03-99 # 3281606 Compound es53 # Check this file using the IUCr facility at: # http://www/iucr.ac.uk/iucr-top/journals/acta/c/services/checkcif.html #**************************************************************************** # The contents of this file between this point and the next #***** line # are held in the file REFCIF.DAT # This is a character file which you may edit to reflect local conditions # # Items which need looking at are represented by a '?' # Items for which there are choices are prefixed with 'choose from' # # 1. SUBMISSION DETAILS _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper. The figures have been sent by mail. ; _publ_contact_author_name 'Prof Stephen G Davies' _publ_contact_author_address ; Dyson Perrins Laboratory University of Oxford South Parks Road OXFORD OX1 3QY UK ; _publ_contact_author_phone ' 01865 270 826 ' _publ_contact_author_fax ' 01865 272 699 ' _publ_contact_author_email ' STEVE.DAVIES@CHEMISTRY.OX.AC.UK ' _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Davies, Stephen G.' 'Bull, Steven D.' 'Fox, David J.' 'Gianotti, Massimo' 'Kelly, Peter M.' 'Pierres, Camille' 'Savory, Edward D.' 'Smith, Andrew D.' #============================================================================= _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 10.5644(2) _cell_angle_alpha 90 _cell_length_b 12.7699(3) _cell_angle_beta 90 _cell_length_c 17.3731(4) _cell_angle_gamma 90 _cell_volume 2343.74(9) _symmetry_cell_setting 'Orthorhombic ' _symmetry_space_group_name_H-M 'P 21 21 21 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 'x+1/2,-y+1/2,-z' '-x,y+1/2,-z+1/2' '-x+1/2,-y,z+1/2' 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 ' 0.0033 0.0016 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 ' 0.0061 0.0033 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 ' 0.0106 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' 'Cl ' 0.1484 0.1585 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' _chemical_formula_sum ' C23 H31 Cl1 N2 O5 ' _chemical_formula_moiety ' C23 H31 Cl1 N2 O5 ' _chemical_compound_source ; ? ; _chemical_formula_weight 450.96 _cell_measurement_reflns_used 2988 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 190 _cell_formula_units_Z 4 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 961.025 _exptl_absorpt_coefficient_mu 0.199 # Sheldrick geometric definitions 0.96 0.97 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 190 _diffrn_reflns_number 5365 _reflns_number_total 5342 _diffrn_reflns_av_R_equivalents 0.00 # Number of reflections with Friedels Law is 5342 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2681 _diffrn_measured_fraction_theta_max 1.000 _reflns_number_gt 3571 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _refine_diff_density_min -0.29 _refine_diff_density_max 0.31 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 3571 _refine_ls_number_parameters 281 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0382 _refine_ls_goodness_of_fit_ref 1.0280 _refine_ls_shift/su_max 0.000345 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Tukey and Prince W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 0.426 0.128 0.216 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type CL1 CL 0.87994(7) 0.66690(5) 0.17760(3) 0.0398 1.0000 Uani C2 C 0.8453(2) 0.67665(19) 0.27554(13) 0.0271 1.0000 Uani N3 N 0.75435(19) 0.61516(16) 0.30150(11) 0.0288 1.0000 Uani C4 C 0.7262(2) 0.62102(19) 0.37671(14) 0.0280 1.0000 Uani C5 C 0.6148(2) 0.55608(19) 0.40585(13) 0.0298 1.0000 Uani N6 N 0.6017(2) 0.45110(15) 0.37336(11) 0.0305 1.0000 Uani C7 C 0.7029(2) 0.37563(19) 0.38876(15) 0.0330 1.0000 Uani C8 C 0.6590(2) 0.26711(19) 0.36332(14) 0.0292 1.0000 Uani C9 C 0.7455(2) 0.1948(2) 0.33542(15) 0.0354 1.0000 Uani C10 C 0.7081(2) 0.0937(2) 0.31485(16) 0.0358 1.0000 Uani C11 C 0.5823(2) 0.06478(19) 0.32242(15) 0.0316 1.0000 Uani O12 O 0.53545(18) -0.03231(14) 0.30339(11) 0.0411 1.0000 Uani C13 C 0.6238(3) -0.1109(2) 0.28069(17) 0.0456 1.0000 Uani C14 C 0.4951(3) 0.1363(2) 0.35064(16) 0.0357 1.0000 Uani C15 C 0.5333(2) 0.2362(2) 0.37106(16) 0.0328 1.0000 Uani C16 C 0.7378(3) 0.3736(2) 0.47362(19) 0.0510 1.0000 Uani C17 C 0.4907(2) 0.61317(19) 0.39062(15) 0.0324 1.0000 Uani C18 C 0.3853(3) 0.56118(19) 0.43608(14) 0.0313 1.0000 Uani O19 O 0.28192(16) 0.54635(14) 0.3929(1) 0.0320 1.0000 Uani C20 C 0.1640(2) 0.5026(2) 0.42744(15) 0.0339 1.0000 Uani C21 C 0.0758(3) 0.4986(2) 0.35897(17) 0.0439 1.0000 Uani C22 C 0.1904(3) 0.3934(2) 0.45865(17) 0.0433 1.0000 Uani C23 C 0.1152(3) 0.5771(2) 0.48881(16) 0.0439 1.0000 Uani O24 O 0.39449(18) 0.53906(15) 0.5032(1) 0.0407 1.0000 Uani C25 C 0.7904(2) 0.6873(2) 0.42641(14) 0.0308 1.0000 Uani C26 C 0.8866(3) 0.75134(19) 0.39801(14) 0.0318 1.0000 Uani C27 C 0.9143(2) 0.74778(18) 0.31997(15) 0.0281 1.0000 Uani O28 O 1.00450(17) 0.80740(14) 0.2843(1) 0.0356 1.0000 Uani C29 C 1.0547(3) 0.8943(2) 0.32686(17) 0.0390 1.0000 Uani O30 O 1.14492(17) 0.86446(15) 0.3801(1) 0.0415 1.0000 Uani C31 C 1.2644(3) 0.8393(3) 0.34583(17) 0.0632 1.0000 Uani H51 H 0.6317 0.5469 0.4631 0.0347 1.0000 Uiso H71 H 0.7810 0.3982 0.3595 0.0392 1.0000 Uiso H91 H 0.8375 0.2159 0.3287 0.0407 1.0000 Uiso H101 H 0.7729 0.0418 0.2934 0.0425 1.0000 Uiso H131 H 0.5807 -0.1784 0.2679 0.0551 1.0000 Uiso H132 H 0.6876 -0.1242 0.3228 0.0551 1.0000 Uiso H133 H 0.6728 -0.0872 0.2333 0.0551 1.0000 Uiso H141 H 0.4032 0.1163 0.3570 0.0422 1.0000 Uiso H151 H 0.4688 0.2872 0.3910 0.0392 1.0000 Uiso H161 H 0.8063 0.3211 0.4848 0.0634 1.0000 Uiso H162 H 0.7648 0.4437 0.4931 0.0634 1.0000 Uiso H163 H 0.6601 0.3512 0.5058 0.0634 1.0000 Uiso H171 H 0.4975 0.6893 0.4066 0.0361 1.0000 Uiso H172 H 0.4700 0.6111 0.3342 0.0361 1.0000 Uiso H211 H -0.0095 0.4710 0.3730 0.0504 1.0000 Uiso H212 H 0.0648 0.5709 0.3356 0.0504 1.0000 Uiso H213 H 0.1127 0.4519 0.3172 0.0504 1.0000 Uiso H221 H 0.1125 0.3620 0.4829 0.0542 1.0000 Uiso H222 H 0.2596 0.3948 0.4987 0.0542 1.0000 Uiso H223 H 0.2187 0.3453 0.4157 0.0542 1.0000 Uiso H231 H 0.0359 0.5484 0.5128 0.0507 1.0000 Uiso H232 H 0.1807 0.5861 0.5305 0.0507 1.0000 Uiso H233 H 0.0963 0.6471 0.4657 0.0507 1.0000 Uiso H251 H 0.7655 0.6887 0.4833 0.0343 1.0000 Uiso H261 H 0.9341 0.8005 0.4334 0.0368 1.0000 Uiso H291 H 1.0946 0.9448 0.2890 0.0460 1.0000 Uiso H292 H 0.9836 0.9310 0.3537 0.0460 1.0000 Uiso H311 H 1.3273 0.8182 0.3852 0.0716 1.0000 Uiso H312 H 1.2982 0.9027 0.3169 0.0716 1.0000 Uiso H313 H 1.2538 0.7809 0.3073 0.0716 1.0000 Uiso H61 H 0.5916 0.4600 0.3175 0.0500 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 0.0480(4) 0.0433(4) 0.0282(3) -0.0002(3) 0.0025(3) -0.0094(3) C2 0.0304(13) 0.0249(12) 0.026(1) 0.002(1) -0.0018(9) 0.004(1) N3 0.029(1) 0.026(1) 0.031(1) 0.0021(8) -0.0006(9) 0.0007(9) C4 0.0273(13) 0.0269(12) 0.0299(12) 0.002(1) -0.004(1) 0.002(1) C5 0.0294(12) 0.0283(12) 0.0317(11) 0.002(1) -0.0025(11) -0.0041(12) N6 0.0322(11) 0.027(1) 0.032(1) 0.0040(9) -0.0034(9) -0.0012(9) C7 0.0279(13) 0.0290(13) 0.0421(14) 0.0060(11) -0.0021(11) -0.0015(11) C8 0.0284(13) 0.0303(13) 0.0289(12) 0.007(1) -0.001(1) -0.001(1) C9 0.0258(12) 0.0413(15) 0.0391(15) 0.0023(12) 0.004(1) -0.0020(11) C10 0.0349(14) 0.0371(14) 0.0355(15) -0.0014(11) 0.0042(12) 0.0059(12) C11 0.0362(14) 0.0282(12) 0.0305(12) 0.0003(11) -0.0039(11) 0.001(1) O12 0.0408(11) 0.0305(9) 0.0519(12) -0.0053(9) -0.0060(9) 0.0007(8) C13 0.0532(18) 0.0332(14) 0.0505(16) -0.0070(12) -0.0060(15) 0.0061(15) C14 0.0274(13) 0.0343(14) 0.0454(15) 0.0038(11) -0.0022(11) -0.0025(12) C15 0.0286(13) 0.0283(12) 0.0414(14) 0.0014(11) 0.0015(11) 0.0046(11) C16 0.067(2) 0.0339(16) 0.0526(17) 0.0038(13) -0.0268(16) 0.0011(15) C17 0.0295(13) 0.0276(12) 0.0402(14) -0.0022(11) 0.0031(11) -0.0028(11) C18 0.0289(13) 0.0270(12) 0.0379(13) -0.004(1) -0.0008(12) 0.0006(12) O19 0.0267(9) 0.0368(9) 0.0325(9) 0.0033(8) -0.0013(7) -0.0044(8) C20 0.0263(13) 0.0370(14) 0.0385(14) -0.0017(11) 0.0021(12) -0.0089(11) C21 0.0324(16) 0.0543(17) 0.0451(15) 0.0003(14) -0.0049(12) -0.0078(13) C22 0.0472(17) 0.0377(16) 0.0450(16) 0.0060(13) 0.0011(13) -0.0089(14) C23 0.0356(14) 0.0497(17) 0.0464(16) -0.0061(13) 0.0073(14) 0.0004(14) O24 0.036(1) 0.0560(11) 0.0296(9) -0.0039(9) 0.0006(8) -0.007(1) C25 0.0296(13) 0.0330(14) 0.0298(12) -0.003(1) 0.001(1) -0.0013(11) C26 0.0330(13) 0.0278(12) 0.0347(12) -0.008(1) -0.0026(12) -0.0014(12) C27 0.0247(12) 0.0229(11) 0.0366(12) 0.0033(11) -0.0003(11) -0.0002(9) O28 0.035(1) 0.0333(9) 0.038(1) 0.0009(8) 0.0018(8) -0.0116(8) C29 0.0395(14) 0.0329(14) 0.0447(15) -0.0003(13) 0.0026(14) -0.0097(12) O30 0.034(1) 0.0542(12) 0.0360(9) -0.0037(8) 0.0009(8) -0.0085(9) C31 0.0358(17) 0.114(3) 0.0401(16) 0.0028(19) 0.0022(13) 0.0024(19) _refine_ls_extinction_coef 330.8(233) _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 Cl1 . C2 . 1.745(2) yes C2 . N3 . 1.320(3) yes C2 . C27 . 1.398(3) yes N3 . C4 . 1.342(3) yes C4 . C5 . 1.526(3) yes C4 . C25 . 1.386(3) yes C5 . N6 . 1.461(3) yes C5 . C17 . 1.523(4) yes C5 . H51 . 1.017 no N6 . C7 . 1.464(3) yes N6 . H61 . 0.983 no C7 . C8 . 1.526(3) yes C7 . C16 . 1.520(4) yes C7 . H71 . 1.012 no C8 . C9 . 1.386(4) yes C8 . C15 . 1.393(4) yes C9 . C10 . 1.397(4) yes C9 . H91 . 1.015 no C10 . C11 . 1.386(4) yes C10 . H101 . 1.023 no C11 . O12 . 1.375(3) yes C11 . C14 . 1.387(4) yes O12 . C13 . 1.426(3) yes C13 . H131 . 1.000 no C13 . H132 . 1.010 no C13 . H133 . 1.019 no C14 . C15 . 1.385(4) yes C14 . H141 . 1.009 no C15 . H151 . 1.004 no C16 . H161 . 1.007 no C16 . H162 . 0.999 no C16 . H163 . 1.034 no C17 . C18 . 1.518(4) yes C17 . H171 . 1.013 no C17 . H172 . 1.005 no C18 . O19 . 1.338(3) yes C18 . O24 . 1.204(3) yes O19 . C20 . 1.491(3) yes C20 . C21 . 1.512(4) yes C20 . C22 . 1.522(4) yes C20 . C23 . 1.519(4) yes C21 . H211 . 0.999 no C21 . H212 . 1.015 no C21 . H213 . 1.016 no C22 . H221 . 1.007 no C22 . H222 . 1.010 no C22 . H223 . 1.012 no C23 . H231 . 1.005 no C23 . H232 . 1.008 no C23 . H233 . 1.000 no C25 . C26 . 1.395(4) yes C25 . H251 . 1.022 no C26 . C27 . 1.388(3) yes C26 . H261 . 1.012 no C27 . O28 . 1.368(3) yes O28 . C29 . 1.435(3) yes C29 . O30 . 1.381(3) yes C29 . H291 . 1.012 no C29 . H292 . 1.000 no O30 . C31 . 1.431(4) yes C31 . H311 . 0.992 no C31 . H312 . 1.017 no C31 . H313 . 1.009 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 Cl1 . C2 . N3 . 116.33(18) yes Cl1 . C2 . C27 . 118.38(18) yes N3 . C2 . C27 . 125.3(2) yes C2 . N3 . C4 . 117.4(2) yes N3 . C4 . C5 . 117.6(2) yes N3 . C4 . C25 . 122.2(2) yes C5 . C4 . C25 . 120.2(2) yes C4 . C5 . N6 . 116.3(2) yes C4 . C5 . C17 . 110.25(19) yes N6 . C5 . C17 . 106.9(2) yes C4 . C5 . H51 . 104.592 no N6 . C5 . H51 . 106.770 no C17 . C5 . H51 . 112.067 no C5 . N6 . C7 . 117.7(2) yes C5 . N6 . H61 . 106.595 no C7 . N6 . H61 . 109.633 no N6 . C7 . C8 . 108.9(2) yes N6 . C7 . C16 . 111.4(2) yes C8 . C7 . C16 . 109.8(2) yes N6 . C7 . H71 . 108.455 no C8 . C7 . H71 . 111.121 no C16 . C7 . H71 . 107.148 no C7 . C8 . C9 . 120.4(2) yes C7 . C8 . C15 . 121.3(2) yes C9 . C8 . C15 . 118.3(2) yes C8 . C9 . C10 . 121.2(2) yes C8 . C9 . H91 . 119.676 no C10 . C9 . H91 . 119.074 no C9 . C10 . C11 . 119.6(2) yes C9 . C10 . H101 . 120.185 no C11 . C10 . H101 . 120.236 no C10 . C11 . O12 . 124.3(2) yes C10 . C11 . C14 . 119.7(2) yes O12 . C11 . C14 . 116.0(2) yes C11 . O12 . C13 . 117.7(2) yes O12 . C13 . H131 . 111.747 no O12 . C13 . H132 . 110.753 no H131 . C13 . H132 . 108.669 no O12 . C13 . H133 . 110.295 no H131 . C13 . H133 . 107.992 no H132 . C13 . H133 . 107.234 no C11 . C14 . C15 . 120.2(2) yes C11 . C14 . H141 . 120.759 no C15 . C14 . H141 . 119.015 no C8 . C15 . C14 . 121.0(2) yes C8 . C15 . H151 . 119.807 no C14 . C15 . H151 . 119.211 no C7 . C16 . H161 . 111.922 no C7 . C16 . H162 . 112.564 no H161 . C16 . H162 . 109.065 no C7 . C16 . H163 . 109.705 no H161 . C16 . H163 . 106.341 no H162 . C16 . H163 . 106.938 no C5 . C17 . C18 . 109.4(2) yes C5 . C17 . H171 . 110.499 no C18 . C17 . H171 . 109.201 no C5 . C17 . H172 . 110.134 no C18 . C17 . H172 . 109.618 no H171 . C17 . H172 . 107.986 no C17 . C18 . O19 . 111.7(2) yes C17 . C18 . O24 . 123.2(2) yes O19 . C18 . O24 . 125.1(2) yes C18 . O19 . C20 . 120.6(2) yes O19 . C20 . C21 . 102.2(2) yes O19 . C20 . C22 . 109.5(2) yes C21 . C20 . C22 . 111.2(2) yes O19 . C20 . C23 . 109.4(2) yes C21 . C20 . C23 . 111.4(2) yes C22 . C20 . C23 . 112.7(2) yes C20 . C21 . H211 . 112.069 no C20 . C21 . H212 . 110.786 no H211 . C21 . H212 . 108.357 no C20 . C21 . H213 . 110.209 no H211 . C21 . H213 . 108.271 no H212 . C21 . H213 . 106.975 no C20 . C22 . H221 . 111.378 no C20 . C22 . H222 . 111.173 no H221 . C22 . H222 . 108.098 no C20 . C22 . H223 . 110.316 no H221 . C22 . H223 . 107.972 no H222 . C22 . H223 . 107.765 no C20 . C23 . H231 . 110.208 no C20 . C23 . H232 . 109.994 no H231 . C23 . H232 . 108.416 no C20 . C23 . H233 . 110.245 no H231 . C23 . H233 . 109.104 no H232 . C23 . H233 . 108.834 no C4 . C25 . C26 . 119.6(2) yes C4 . C25 . H251 . 119.147 no C26 . C25 . H251 . 121.241 no C25 . C26 . C27 . 118.7(2) yes C25 . C26 . H261 . 120.709 no C27 . C26 . H261 . 120.590 no C2 . C27 . C26 . 116.8(2) yes C2 . C27 . O28 . 118.4(2) yes C26 . C27 . O28 . 124.8(2) yes C27 . O28 . C29 . 117.1(2) yes O28 . C29 . O30 . 112.7(2) yes O28 . C29 . H291 . 108.186 no O30 . C29 . H291 . 108.827 no O28 . C29 . H292 . 108.946 no O30 . C29 . H292 . 109.614 no H291 . C29 . H292 . 108.464 no C29 . O30 . C31 . 113.1(2) yes O30 . C31 . H311 . 111.404 no O30 . C31 . H312 . 109.679 no H311 . C31 . H312 . 108.750 no O30 . C31 . H313 . 110.101 no H311 . C31 . H313 . 109.416 no H312 . C31 . H313 . 107.394 no