# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Christopher, Easton' 'Alison J, Edwards' 'Stephen B, McNabb' 'Martin C, Merrett' ; Jenny L, O'Connell ; 'Jamie S, Simpson' 'Anthony C, Willis' _publ_contact_author_name 'Prof Christopher Easton' _publ_contact_author_address ; Research School of Chemistry Australian National University Science Road Canberra ACT 2601 AUSTRALIA ; _publ_contact_author_email easton@rsc.anu.edu.au _publ_contact_author_fax ' 61 2 6125 8114 ' _publ_contact_author_phone ' 61 2 6125 8201 ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category ? _publ_requested_coeditor_name ? _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Allylic halogenation of unsaturated amino acids ; data_sbm10 _database_code_CSD 207407 _audit_creation_date 02-15-03 _audit_creation_method CRYSTALS_ver_12-03-99 # 3051300 sbm10 _audit_update_record ; 2002-03-14 - Report on C14 H11 N O4 by Anthony C. Willis for Stephen B. McNabb and Christopher J. Easton 2002-03-14 - passes checkcif tests with minor warnings 2002-03-15 - make both molecules (as presented) same hand 2002-03-19 - checkcif run again ; #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Allylic halogenation of unsaturated amino acids ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~14~H~11~NO~4~ is reported. ; _publ_section_comment #Text of the paper ; The crystal is racemic. The crystallographic asymmetric unit consists of two independent molecules of C~14~H~11~NO~4~. The structure exhibits some non-crystallographic translational pseudo-symmetry. Agreement factors are satisfactory for all classes of reflection and equivalent bond lengths and angles are comparable for each molecule, indicating that no systematic error has occurred. Hydrogen atoms attached to carbon atoms were included at idealized positions and ride on the atoms to which they were bonded. Two peaks in the final difference electron density map are significantly larger than the rest. One is close to H(31) and C(3), and the other close to H(1032) and C(103), i.e., cis to C(1) and C(101), respectively, and in very similar positions in each molecule. They possibly indicate the presence of some minor impurity which has co-crystallised with the C~14~H~11~NO~4~. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms bonded to C ride on the atoms to which they were bonded. ; _publ_section_exptl_prep ; The compound was prepared by SBM and recrystallized from dichloromethane. ; #========================================================================== _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 ; teXsan (MSC, 1992-1997) ; #============================================================= _cell_length_a 7.0050(2) _cell_angle_alpha 91.151(1) _cell_length_b 12.8848(4) _cell_angle_beta 94.660(1) _cell_length_c 13.7023(5) _cell_angle_gamma 90.007(2) _cell_volume 1232.40(7) _symmetry_cell_setting 'Triclinic ' _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 _chemical_formula_sum ' C14 H11 N O4 ' _chemical_formula_moiety ' C14 H11 N O4 ' _chemical_compound_source ; ? ; _chemical_formula_weight 257.24 _cell_measurement_reflns_used 17604 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 200 _cell_formula_units_Z 4 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_max 0.27 _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 536.301 _exptl_absorpt_coefficient_mu 0.103 # Sheldrick geometric definitions 0.97 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 ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 2 deg at rate 20 sec/frame, crystal-detector distance 28mm, multiple scan sets so over 90 percent of data collected with 2-fold redundancy or more. ; # 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 0.150 0 -1 0 0.120 0 0 1 0.100 0 0 -1 0.170 1 0 -1 0.120 -1 0 1 0.080 0 1 -1 0.120 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 200 _diffrn_reflns_number 27671 _reflns_number_total 5653 _diffrn_reflns_av_R_equivalents 0.06 # Number of reflections with Friedels Law is 5653 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5691 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_theta_full 27.55 _reflns_number_gt 2685 _diffrn_reflns_theta_min 4.28 _diffrn_reflns_theta_max 27.55 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -16 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _refine_diff_density_min -0.19 _refine_diff_density_max 0.76 _reflns_threshold_expression >2.00\s(I) _refine_ls_number_reflns 2685 _refine_ls_number_parameters 343 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.0507 _refine_ls_goodness_of_fit_ref 1.0651 _refine_ls_shift/su_max 0.001128 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 0.400 0.218 0.136 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Carruthers, J.R. & Watkin, D.J. (1979) Acta Cryst., A35, 698-699. 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. Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. ; # 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 O1 o -0.0925(3) 0.6276(2) 0.30718(16) 0.0577 1.0000 Uani O2 o 0.0875(3) 0.60626(17) 0.18044(14) 0.0454 1.0000 Uani O3 o 0.2592(3) 0.52347(16) 0.50786(14) 0.0470 1.0000 Uani O4 o 0.1535(3) 0.85522(16) 0.40385(15) 0.0457 1.0000 Uani O11 o 0.0338(3) 0.14421(19) 0.04952(15) 0.0521 1.0000 Uani O12 o 0.1734(3) 0.15230(17) -0.09130(14) 0.0452 1.0000 Uani O13 o 0.4171(3) 0.01733(16) 0.19221(15) 0.0503 1.0000 Uani O14 o 0.2835(3) 0.36335(16) 0.17365(15) 0.0482 1.0000 Uani N1 n 0.2224(3) 0.68239(17) 0.43233(16) 0.0337 1.0000 Uani N11 n 0.3681(3) 0.19039(17) 0.15882(16) 0.0339 1.0000 Uani C1 c 0.2448(4) 0.6508(2) 0.33314(19) 0.0329 1.0000 Uani C2 c 0.4121(4) 0.6919(2) 0.2860(2) 0.0359 1.0000 Uani C3 c 0.4897(5) 0.7770(3) 0.2552(2) 0.0485 1.0000 Uani C4 c 0.4234(4) 0.5839(2) 0.3125(2) 0.0398 1.0000 Uani C5 c 0.0609(4) 0.6277(2) 0.2747(2) 0.0357 1.0000 Uani C6 c -0.0814(5) 0.5774(3) 0.1186(2) 0.0601 1.0000 Uani C7 c 0.2321(4) 0.6157(2) 0.51212(19) 0.0336 1.0000 Uani C8 c 0.2026(4) 0.6830(2) 0.59902(19) 0.0340 1.0000 Uani C9 c 0.2011(4) 0.6573(3) 0.6965(2) 0.0413 1.0000 Uani C10 c 0.1656(4) 0.7368(3) 0.7626(2) 0.0463 1.0000 Uani C11 c 0.1343(4) 0.8375(3) 0.7309(2) 0.0465 1.0000 Uani C12 c 0.1358(4) 0.8634(2) 0.6327(2) 0.0409 1.0000 Uani C13 c 0.1708(4) 0.7833(2) 0.56798(19) 0.0338 1.0000 Uani C14 c 0.1795(4) 0.7847(2) 0.4598(2) 0.0349 1.0000 Uani C101 c 0.3666(4) 0.1842(2) 0.05433(19) 0.0356 1.0000 Uani C102 c 0.5028(4) 0.2502(3) 0.0063(2) 0.0436 1.0000 Uani C103 c 0.5463(5) 0.3484(3) -0.0129(2) 0.0644 1.0000 Uani C104 c 0.5460(4) 0.1411(3) 0.0083(2) 0.0460 1.0000 Uani C105 c 0.1729(4) 0.1585(2) 0.0055(2) 0.0355 1.0000 Uani C106 c -0.0085(5) 0.1246(3) -0.1440(2) 0.0521 1.0000 Uani C107 c 0.3867(4) 0.1050(2) 0.2200(2) 0.0353 1.0000 Uani C108 c 0.3619(4) 0.1454(2) 0.32050(19) 0.0326 1.0000 Uani C109 c 0.3658(4) 0.0937(2) 0.4080(2) 0.0380 1.0000 Uani C110 c 0.3329(4) 0.1529(2) 0.4915(2) 0.0425 1.0000 Uani C111 c 0.2965(4) 0.2588(2) 0.4862(2) 0.0400 1.0000 Uani C112 c 0.2908(4) 0.3099(2) 0.3970(2) 0.0376 1.0000 Uani C113 c 0.3243(4) 0.2505(2) 0.3149(2) 0.0324 1.0000 Uani C114 c 0.3209(4) 0.2809(2) 0.2109(2) 0.0356 1.0000 Uani H31 h 0.4238(5) 0.8453(3) 0.2622(2) 0.0584 1.0000 Uiso H32 h 0.6145(5) 0.7734(3) 0.2247(2) 0.0584 1.0000 Uiso H41 h 0.5148(4) 0.5616(2) 0.3680(2) 0.0478 1.0000 Uiso H42 h 0.4130(4) 0.5282(2) 0.2605(2) 0.0478 1.0000 Uiso H61 h -0.0457(5) 0.5632(3) 0.0505(2) 0.0709 1.0000 Uiso H62 h -0.1763(5) 0.6354(3) 0.1182(2) 0.0709 1.0000 Uiso H63 h -0.1393(5) 0.5136(3) 0.1445(2) 0.0709 1.0000 Uiso H91 h 0.2245(4) 0.5845(3) 0.7184(2) 0.0496 1.0000 Uiso H101 h 0.1626(4) 0.7214(3) 0.8337(2) 0.0555 1.0000 Uiso H111 h 0.1098(4) 0.8932(3) 0.7802(2) 0.0556 1.0000 Uiso H121 h 0.1129(4) 0.9361(2) 0.6103(2) 0.0491 1.0000 Uiso H1031 h 0.6591(5) 0.3636(3) -0.0506(2) 0.0773 1.0000 Uiso H1032 h 0.4662(5) 0.4066(3) 0.0106(2) 0.0773 1.0000 Uiso H1041 h 0.6575(4) 0.1152(3) 0.0512(2) 0.0553 1.0000 Uiso H1042 h 0.5315(4) 0.0981(3) -0.0535(2) 0.0553 1.0000 Uiso H1061 h 0.0068(5) 0.1220(3) -0.2159(2) 0.0614 1.0000 Uiso H1062 h -0.1070(5) 0.1778(3) -0.1297(2) 0.0614 1.0000 Uiso H1063 h -0.0504(5) 0.0550(3) -0.1226(2) 0.0614 1.0000 Uiso H1091 h 0.3910(4) 0.0174(2) 0.4114(2) 0.0455 1.0000 Uiso H1101 h 0.3356(4) 0.1185(2) 0.5563(2) 0.0511 1.0000 Uiso H1111 h 0.2739(4) 0.2991(2) 0.5473(2) 0.0479 1.0000 Uiso H1121 h 0.2636(4) 0.3859(2) 0.3926(2) 0.0450 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 0.0388(12) 0.0922(18) 0.0421(13) -0.0101(12) 0.007(1) -0.0093(11) O2 0.0466(12) 0.0604(14) 0.0281(11) -0.0081(9) -0.0010(9) -0.004(1) O3 0.0667(14) 0.0375(13) 0.0375(12) 0.0018(9) 0.009(1) 0.007(1) O4 0.0603(13) 0.0374(12) 0.0400(12) 0.005(1) 0.008(1) 0.001(1) O11 0.0395(12) 0.0816(17) 0.0355(12) -0.0057(11) 0.0073(9) -0.0088(11) O12 0.0437(12) 0.0649(14) 0.026(1) -0.0019(9) -0.0015(8) -0.014(1) O13 0.0728(15) 0.0366(13) 0.0415(12) -0.006(1) 0.0064(11) 0.003(1) O14 0.0673(14) 0.0378(13) 0.0398(12) 0.001(1) 0.006(1) 0.006(1) N1 0.0397(13) 0.0351(13) 0.0264(12) -0.003(1) 0.005(1) 0.001(1) N11 0.0403(13) 0.0355(13) 0.0256(12) -0.003(1) 0.0013(9) -0.000(1) C1 0.0378(15) 0.0345(15) 0.0267(14) -0.0025(11) 0.0047(11) -0.0002(11) C2 0.0386(15) 0.0406(17) 0.0287(14) -0.0024(12) 0.0044(11) -0.0005(12) C3 0.0501(19) 0.063(2) 0.0330(16) 0.0002(15) 0.0066(13) -0.0047(15) C4 0.0421(16) 0.0430(18) 0.0344(15) -0.0052(13) 0.0046(12) 0.0047(12) C5 0.0407(16) 0.0367(16) 0.0296(15) -0.0019(12) 0.0045(12) -0.0004(12) C6 0.062(2) 0.079(3) 0.0365(18) -0.0083(17) -0.0114(15) -0.0126(18) C7 0.0337(14) 0.0391(18) 0.0278(14) 0.0026(12) 0.0013(11) -0.0006(12) C8 0.0268(13) 0.0471(18) 0.0282(15) -0.0024(13) 0.0034(11) 0.0002(11) C9 0.0335(15) 0.061(2) 0.0293(15) 0.0036(14) 0.0032(11) 0.0042(13) C10 0.0339(15) 0.075(2) 0.0296(15) -0.0036(15) 0.0036(12) 0.0014(14) C11 0.0345(16) 0.068(2) 0.0364(17) -0.0189(15) 0.0054(13) -0.0042(14) C12 0.0344(15) 0.0439(18) 0.0444(18) -0.0100(14) 0.0061(12) -0.0042(12) C13 0.0286(14) 0.0424(18) 0.0307(15) -0.0044(12) 0.0046(11) -0.0047(11) C14 0.0316(14) 0.0398(17) 0.0333(16) -0.0043(13) 0.0035(11) -0.0030(12) C101 0.0355(15) 0.0445(17) 0.0263(14) -0.0057(12) 0.0021(11) -0.0037(12) C102 0.0428(17) 0.057(2) 0.0308(16) -0.0030(14) 0.0037(12) -0.0153(14) C103 0.054(2) 0.100(3) 0.0398(19) 0.0018(19) 0.0043(15) -0.023(2) C104 0.0401(17) 0.064(2) 0.0336(16) -0.0072(14) 0.0057(13) -0.0024(14) C105 0.0399(16) 0.0362(16) 0.0302(15) -0.0025(12) 0.0029(12) -0.0006(12) C106 0.0526(19) 0.063(2) 0.0382(18) -0.0023(15) -0.0124(14) -0.0129(16) C107 0.0361(15) 0.0349(17) 0.0344(15) -0.0037(13) 0.0012(12) -0.0015(12) C108 0.0293(14) 0.0394(16) 0.0285(14) -0.0036(12) -0.0006(11) -0.0042(11) C109 0.0367(15) 0.0420(17) 0.0351(16) 0.0010(13) 0.0010(12) 0.0009(12) C110 0.0350(15) 0.058(2) 0.0344(16) 0.0028(14) 0.0028(12) -0.0043(13) C111 0.0321(15) 0.055(2) 0.0332(16) -0.0105(13) 0.0050(11) -0.0056(13) C112 0.0334(14) 0.0400(17) 0.0390(16) -0.0087(13) 0.0030(12) -0.0036(12) C113 0.0280(13) 0.0361(16) 0.0324(14) -0.0033(12) 0.0002(11) -0.0047(11) C114 0.0334(15) 0.0364(18) 0.0365(16) -0.0030(13) 0.0014(12) -0.0027(12) _refine_ls_extinction_method None 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 . C5 . 1.196(3) yes O2 . C5 . 1.343(3) yes O2 . C6 . 1.442(4) yes O3 . C7 . 1.205(3) yes O4 . C14 . 1.205(3) yes O11 . C105 . 1.203(3) yes O12 . C105 . 1.327(3) yes O12 . C106 . 1.453(3) yes O13 . C107 . 1.209(3) yes O14 . C114 . 1.207(3) yes N1 . C1 . 1.432(3) yes N1 . C7 . 1.401(4) yes N1 . C14 . 1.404(4) yes N11 . C101 . 1.432(3) yes N11 . C107 . 1.396(4) yes N11 . C114 . 1.409(3) yes C1 . C2 . 1.485(4) yes C1 . C4 . 1.561(4) yes C1 . C5 . 1.488(4) yes C2 . C3 . 1.317(4) yes C2 . C4 . 1.445(4) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no C4 . H41 . 1.000 no C4 . H42 . 1.000 no C6 . H61 . 1.000 no C6 . H62 . 1.000 no C6 . H63 . 1.000 no C7 . C8 . 1.487(4) yes C8 . C9 . 1.383(4) yes C8 . C13 . 1.382(4) yes C9 . C10 . 1.391(4) yes C9 . H91 . 1.000 no C10 . C11 . 1.388(5) yes C10 . H101 . 1.000 no C11 . C12 . 1.394(4) yes C11 . H111 . 1.000 no C12 . C13 . 1.383(4) yes C12 . H121 . 1.000 no C13 . C14 . 1.489(4) yes C101 . C102 . 1.480(4) yes C101 . C104 . 1.550(4) yes C101 . C105 . 1.497(4) yes C102 . C103 . 1.338(5) yes C102 . C104 . 1.439(5) yes C103 . H1031 . 1.000 no C103 . H1032 . 1.000 no C104 . H1041 . 1.000 no C104 . H1042 . 1.000 no C106 . H1061 . 1.000 no C106 . H1062 . 1.000 no C106 . H1063 . 1.000 no C107 . C108 . 1.486(4) yes C108 . C109 . 1.381(4) yes C108 . C113 . 1.383(4) yes C109 . C110 . 1.398(4) yes C109 . H1091 . 1.000 no C110 . C111 . 1.390(4) yes C110 . H1101 . 1.000 no C111 . C112 . 1.398(4) yes C111 . H1111 . 1.000 no C112 . C113 . 1.383(4) yes C112 . H1121 . 1.000 no C113 . C114 . 1.485(4) 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 C5 . O2 . C6 . 116.0(2) yes C105 . O12 . C106 . 115.6(2) yes C1 . N1 . C7 . 124.9(2) yes C1 . N1 . C14 . 123.0(2) yes C7 . N1 . C14 . 112.1(2) yes C101 . N11 . C107 . 124.4(2) yes C101 . N11 . C114 . 123.5(2) yes C107 . N11 . C114 . 111.4(2) yes N1 . C1 . C2 . 117.8(2) yes N1 . C1 . C4 . 117.9(2) yes C2 . C1 . C4 . 56.58(18) yes N1 . C1 . C5 . 113.9(2) yes C2 . C1 . C5 . 120.9(2) yes C4 . C1 . C5 . 118.1(2) yes C1 . C2 . C3 . 143.8(3) yes C1 . C2 . C4 . 64.35(19) yes C3 . C2 . C4 . 151.3(3) yes C2 . C3 . H31 . 120.00(19) no C2 . C3 . H32 . 120.00(19) no H31 . C3 . H32 . 120.000 no C1 . C4 . C2 . 59.07(18) yes C1 . C4 . H41 . 120.16(14) no C2 . C4 . H41 . 120.16(16) no C1 . C4 . H42 . 120.16(14) no C2 . C4 . H42 . 120.16(16) no H41 . C4 . H42 . 109.467 no O1 . C5 . O2 . 123.8(3) yes O1 . C5 . C1 . 124.5(3) yes O2 . C5 . C1 . 111.8(2) yes O2 . C6 . H61 . 109.47(17) no O2 . C6 . H62 . 109.47(18) no H61 . C6 . H62 . 109.476 no O2 . C6 . H63 . 109.47(18) no H61 . C6 . H63 . 109.476 no H62 . C6 . H63 . 109.476 no O3 . C7 . N1 . 125.4(2) yes O3 . C7 . C8 . 129.1(3) yes N1 . C7 . C8 . 105.5(2) yes C7 . C8 . C9 . 129.7(3) yes C7 . C8 . C13 . 108.5(2) yes C9 . C8 . C13 . 121.8(3) yes C8 . C9 . C10 . 117.2(3) yes C8 . C9 . H91 . 121.40(18) no C10 . C9 . H91 . 121.40(19) no C9 . C10 . C11 . 120.7(3) yes C9 . C10 . H101 . 119.67(19) no C11 . C10 . H101 . 119.67(17) no C10 . C11 . C12 . 122.1(3) yes C10 . C11 . H111 . 118.93(17) no C12 . C11 . H111 . 118.93(19) no C11 . C12 . C13 . 116.4(3) yes C11 . C12 . H121 . 121.79(19) no C13 . C12 . H121 . 121.79(18) no C8 . C13 . C12 . 121.7(3) yes C8 . C13 . C14 . 108.5(2) yes C12 . C13 . C14 . 129.7(3) yes O4 . C14 . N1 . 124.8(2) yes O4 . C14 . C13 . 129.9(3) yes N1 . C14 . C13 . 105.3(2) yes N11 . C101 . C102 . 118.1(2) yes N11 . C101 . C104 . 118.6(2) yes C102 . C101 . C104 . 56.64(19) yes N11 . C101 . C105 . 112.8(2) yes C102 . C101 . C105 . 121.2(2) yes C104 . C101 . C105 . 118.6(2) yes C101 . C102 . C103 . 143.8(3) yes C101 . C102 . C104 . 64.1(2) yes C103 . C102 . C104 . 151.8(3) yes C102 . C103 . H1031 . 120.0(2) no C102 . C103 . H1032 . 120.0(2) no H1031 . C103 . H1032 . 120.000 no C101 . C104 . C102 . 59.23(19) yes C101 . C104 . H1041 . 120.13(15) no C102 . C104 . H1041 . 120.13(17) no C101 . C104 . H1042 . 120.13(15) no C102 . C104 . H1042 . 120.13(17) no H1041 . C104 . H1042 . 109.467 no O11 . C105 . O12 . 124.2(3) yes O11 . C105 . C101 . 123.5(2) yes O12 . C105 . C101 . 112.3(2) yes O12 . C106 . H1061 . 109.47(15) no O12 . C106 . H1062 . 109.47(16) no H1061 . C106 . H1062 . 109.476 no O12 . C106 . H1063 . 109.47(16) no H1061 . C106 . H1063 . 109.476 no H1062 . C106 . H1063 . 109.476 no O13 . C107 . N11 . 124.3(3) yes O13 . C107 . C108 . 129.5(3) yes N11 . C107 . C108 . 106.2(2) yes C107 . C108 . C109 . 130.0(3) yes C107 . C108 . C113 . 108.1(2) yes C109 . C108 . C113 . 121.9(2) yes C108 . C109 . C110 . 116.9(3) yes C108 . C109 . H1091 . 121.56(16) no C110 . C109 . H1091 . 121.56(18) no C109 . C110 . C111 . 121.3(3) yes C109 . C110 . H1101 . 119.33(18) no C111 . C110 . H1101 . 119.33(17) no C110 . C111 . C112 . 121.1(3) yes C110 . C111 . H1111 . 119.43(17) no C112 . C111 . H1111 . 119.43(17) no C111 . C112 . C113 . 117.0(3) yes C111 . C112 . H1121 . 121.51(17) no C113 . C112 . H1121 . 121.51(17) no C108 . C113 . C112 . 121.8(3) yes C108 . C113 . C114 . 108.6(2) yes C112 . C113 . C114 . 129.6(3) yes O14 . C114 . N11 . 124.4(3) yes O14 . C114 . C113 . 130.1(3) yes N11 . C114 . C113 . 105.5(2) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O(1) C(5) O(2) C(6) . . . . -2.8(4) no O(1) C(5) C(1) N(1) . . . . -5.1(4) no O(1) C(5) C(1) C(2) . . . . -154.5(3) no O(1) C(5) C(1) C(4) . . . . 139.6(3) no O(2) C(5) C(1) N(1) . . . . 175.2(2) no O(2) C(5) C(1) C(2) . . . . 25.9(3) no O(2) C(5) C(1) C(4) . . . . -40.1(3) no O(3) C(7) N(1) C(1) . . . . -0.5(4) no O(3) C(7) N(1) C(14) . . . . 176.9(3) no O(3) C(7) C(8) C(9) . . . . 0.9(5) no O(3) C(7) C(8) C(13) . . . . -178.1(3) no O(4) C(14) N(1) C(1) . . . . 1.6(4) no O(4) C(14) N(1) C(7) . . . . -175.9(3) no O(4) C(14) C(13) C(8) . . . . 177.2(3) no O(4) C(14) C(13) C(12) . . . . -2.0(5) no O(11) C(105) O(12) C(106) . . . . -1.0(4) no O(11) C(105) C(101) N(11) . . . . -0.3(4) no O(11) C(105) C(101) C(102) . . . . -148.7(3) no O(11) C(105) C(101) C(104) . . . . 145.0(3) no O(12) C(105) C(101) N(11) . . . . -179.6(2) no O(12) C(105) C(101) C(102) . . . . 32.0(4) no O(12) C(105) C(101) C(104) . . . . -34.4(3) no O(13) C(107) N(11) C(101) . . . . 5.5(4) no O(13) C(107) N(11) C(114) . . . . 176.1(3) no O(13) C(107) C(108) C(109) . . . . -0.5(5) no O(13) C(107) C(108) C(113) . . . . -178.2(3) no O(14) C(114) N(11) C(101) . . . . -3.7(4) no O(14) C(114) N(11) C(107) . . . . -174.5(3) no O(14) C(114) C(113) C(108) . . . . 175.6(3) no O(14) C(114) C(113) C(112) . . . . -2.2(5) no N(1) C(1) C(2) C(3) . . . . -65.7(5) no N(1) C(1) C(2) C(4) . . . . 106.7(3) no N(1) C(1) C(4) C(2) . . . . -106.4(3) no N(1) C(7) C(8) C(9) . . . . -179.0(3) no N(1) C(7) C(8) C(13) . . . . 2.0(3) no N(1) C(14) C(13) C(8) . . . . -1.6(3) no N(1) C(14) C(13) C(12) . . . . 179.2(3) no N(11) C(101) C(102) C(103) . . . . -67.4(5) no N(11) C(101) C(102) C(104) . . . . 107.4(3) no N(11) C(101) C(104) C(102) . . . . -106.4(3) no N(11) C(107) C(108) C(109) . . . . 179.6(3) no N(11) C(107) C(108) C(113) . . . . 1.8(3) no N(11) C(114) C(113) C(108) . . . . -3.1(3) no N(11) C(114) C(113) C(112) . . . . 179.1(3) no C(1) N(1) C(7) C(8) . . . . 179.4(2) no C(1) N(1) C(14) C(13) . . . . -179.5(2) no C(1) C(4) C(2) C(3) . . . . 170.6(6) no C(1) C(5) O(2) C(6) . . . . 176.9(2) no C(2) C(1) N(1) C(7) . . . . -115.4(3) no C(2) C(1) N(1) C(14) . . . . 67.4(3) no C(2) C(4) C(1) C(5) . . . . 110.3(3) no C(3) C(2) C(1) C(4) . . . . -172.4(5) no C(3) C(2) C(1) C(5) . . . . 82.5(5) no C(4) C(1) N(1) C(7) . . . . -50.6(3) no C(4) C(1) N(1) C(14) . . . . 132.3(3) no C(4) C(2) C(1) C(5) . . . . -105.2(3) no C(5) C(1) N(1) C(7) . . . . 94.2(3) no C(5) C(1) N(1) C(14) . . . . -83.0(3) no C(7) N(1) C(14) C(13) . . . . 3.0(3) no C(7) C(8) C(9) C(10) . . . . -178.7(3) no C(7) C(8) C(13) C(12) . . . . 179.1(3) no C(7) C(8) C(13) C(14) . . . . -0.3(3) no C(8) C(7) N(1) C(14) . . . . -3.1(3) no C(8) C(9) C(10) C(11) . . . . -0.3(4) no C(8) C(13) C(12) C(11) . . . . 0.0(4) no C(9) C(8) C(13) C(12) . . . . 0.0(4) no C(9) C(8) C(13) C(14) . . . . -179.3(3) no C(9) C(10) C(11) C(12) . . . . 0.4(4) no C(10) C(9) C(8) C(13) . . . . 0.2(4) no C(10) C(11) C(12) C(13) . . . . -0.2(4) no C(11) C(12) C(13) C(14) . . . . 179.2(3) no C(101) N(11) C(107) C(108) . . . . -174.6(2) no C(101) N(11) C(114) C(113) . . . . 175.1(2) no C(101) C(104) C(102) C(103) . . . . 173.4(6) no C(101) C(105) O(12) C(106) . . . . 178.3(2) no C(102) C(101) N(11) C(107) . . . . -126.7(3) no C(102) C(101) N(11) C(114) . . . . 63.7(4) no C(102) C(104) C(101) C(105) . . . . 110.4(3) no C(103) C(102) C(101) C(104) . . . . -174.7(5) no C(103) C(102) C(101) C(105) . . . . 79.5(5) no C(104) C(101) N(11) C(107) . . . . -61.5(4) no C(104) C(101) N(11) C(114) . . . . 128.9(3) no C(104) C(102) C(101) C(105) . . . . -105.8(3) no C(105) C(101) N(11) C(107) . . . . 83.7(3) no C(105) C(101) N(11) C(114) . . . . -85.8(3) no C(107) N(11) C(114) C(113) . . . . 4.3(3) no C(107) C(108) C(109) C(110) . . . . -178.5(3) no C(107) C(108) C(113) C(112) . . . . 178.8(3) no C(107) C(108) C(113) C(114) . . . . 0.8(3) no C(108) C(107) N(11) C(114) . . . . -3.9(3) no C(108) C(109) C(110) C(111) . . . . 0.5(4) no C(108) C(113) C(112) C(111) . . . . 0.0(4) no C(109) C(108) C(113) C(112) . . . . 0.8(4) no C(109) C(108) C(113) C(114) . . . . -177.2(3) no C(109) C(110) C(111) C(112) . . . . 0.2(4) no C(110) C(109) C(108) C(113) . . . . -1.0(4) no C(110) C(111) C(112) C(113) . . . . -0.5(4) no C(111) C(112) C(113) C(114) . . . . 177.5(3) no #------------------------------------------------------------------------------ #===END # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_CESM13z _database_code_CSD 207408 _audit_creation_date 02-20-03 _audit_creation_method 'maXus + CRYSTALS_ver_12-03-99' _publ_section_title ; Allylic halogenation of unsaturated amino acids ; _publ_section_abstract ; ; _publ_section_comment ; The crystals provided for this study were of poor quality. The relative stereochemistry is unambiguously determined in this study of the racemic material. As a result of the poor crystal quality, the data set and hence the structure is of marginal quality. Any interpretation of the data presented here exceeding simple discussion of the atomic connectivity is unjustified. ; _publ_section_synopsis ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description prism _exptl_crystal_colour Colourless _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment noref _diffrn_measurement_device KappaCCD _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution ; SIR97 (Altomare et al, 1999) ; _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.02777 _diffrn_orient_matrix_UB_12 0.09178 _diffrn_orient_matrix_UB_13 -0.09401 _diffrn_orient_matrix_UB_21 0.06805 _diffrn_orient_matrix_UB_22 -0.02598 _diffrn_orient_matrix_UB_23 -0.00526 _diffrn_orient_matrix_UB_31 -0.02117 _diffrn_orient_matrix_UB_32 -0.04484 _diffrn_orient_matrix_UB_33 -0.05240 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 328.151 _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' _symmetry_space_group_name_H-M 'P 21/a ' _symmetry_cell_setting Monoclinic _chemical_formula_moiety 'C14 H11 Cl2 N O4 ' _chemical_formula_sum 'C14 H11 Cl2 N O4 ' _chemical_name_systematic ; ? ; _cell_length_a 7.4491(5) _cell_length_b 13.6937(10) _cell_length_c 13.8646(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.317(3) _cell_angle_gamma 90.00 _cell_volume 1413.9(2) _diffrn_reflns_number 14725 _diffrn_reflns_theta_max 25.41 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_full 25.41 _cell_measurement_reflns_used 70015 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 25.350 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _diffrn_reflns_av_R_equivalents 0.210 # 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 0.090 0 -1 0 0.080 0 0 1 0.040 0 0 -1 0.030 -1 0 0 0.280 1 0 0 0.250 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.848 _exptl_absorpt_correction_T_max 0.968 _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.53 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; _exptl_absorpt_coefficient_mu 0.47 _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 ' 0.0033 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 '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 '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 # Refinement statistics _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _reflns_d_resolution_low 1.86 _reflns_d_resolution_high 0.64 _diffrn_measured_fraction_theta_max 0.963 _reflns_number_total 2483 _reflns_number_gt 1444 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _refine_diff_density_min -0.47 _refine_diff_density_max 0.38 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 1444 _refine_ls_number_parameters 190 _refine_ls_R_factor_gt 0.0864 _refine_ls_wR_factor_ref 0.0944 _refine_ls_goodness_of_fit_ref 1.0057 _refine_ls_shift/su_max 0.000167 _refine_ls_matrix_type full _refine_ls_structure_factor_coef F _refine_ls_extinction_method None _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 0.767 1.57 -.324 ; _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) + maXus(Mackay et al., 1999) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) + maXus(Mackay et al., 1999) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #================================================== _publ_section_references ; COLLECT Software, Nonius BV 1997-2001) Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker 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. Carruthers, J.R. and Watkin, D.J. (1979), Acta Cryst, A35, 698-699 Coppens, P. (1970). In Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P.Huber, pp 255-270. Copenhagen: Munksgaard. 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 1.1702(2) 0.03728(15) 0.62979(14) 0.0713 1.0000 Uani Cl2 cl 0.6510(2) 0.06760(12) 0.60501(16) 0.0737 1.0000 Uani O1 o 1.1482(7) -0.0944(3) 0.8044(4) 0.0739 1.0000 Uani O2 o 0.8998(6) -0.1513(3) 0.7319(4) 0.0688 1.0000 Uani O3 o 0.9729(7) 0.2256(3) 0.6537(4) 0.0729 1.0000 Uani O4 o 0.8470(7) 0.0060(3) 0.8923(4) 0.0735 1.0000 Uani N1 n 0.9334(8) 0.0949(4) 0.7594(4) 0.0594 1.0000 Uani C1 c 1.0175(9) -0.0817(5) 0.7542(5) 0.0598 1.0000 Uani C2 c 0.9725(9) 0.0140(4) 0.6968(5) 0.0565 1.0000 Uani C3 c 0.8187(9) -0.0216(4) 0.6277(5) 0.0567 1.0000 Uani C4 c 0.7470(9) -0.1178(5) 0.6689(5) 0.0630 1.0000 Uani C5 c 0.583(1) -0.1086(6) 0.7333(6) 0.0786 1.0000 Uani C6 c 0.7201(12) -0.1943(5) 0.5923(6) 0.0791 1.0000 Uani C7 c 0.9396(9) 0.1955(5) 0.7314(5) 0.0587 1.0000 Uani C8 c 0.8916(9) 0.2505(4) 0.8199(5) 0.0586 1.0000 Uani C9 c 0.880(1) 0.3497(5) 0.8383(6) 0.0723 1.0000 Uani C10 c 0.830(1) 0.3803(5) 0.9265(6) 0.0683 1.0000 Uani C11 c 0.788(1) 0.3132(5) 0.9985(6) 0.0726 1.0000 Uani C12 c 0.801(1) 0.2139(5) 0.9836(6) 0.0698 1.0000 Uani C13 c 0.8546(9) 0.1832(4) 0.8931(5) 0.0580 1.0000 Uani C14 c 0.877(1) 0.0830(5) 0.8544(5) 0.0634 1.0000 Uani H31 h 0.8673(9) -0.0337(4) 0.5621(5) 0.0681 1.0000 Uiso H51 h 0.476(1) -0.0863(6) 0.6939(6) 0.0920 1.0000 Uiso H52 h 0.609(1) -0.0600(6) 0.7854(6) 0.0920 1.0000 Uiso H53 h 0.556(1) -0.1735(6) 0.7628(6) 0.0920 1.0000 Uiso H61 h 0.6185(12) -0.1746(5) 0.5481(6) 0.0937 1.0000 Uiso H62 h 0.6924(12) -0.2588(5) 0.6224(6) 0.0937 1.0000 Uiso H63 h 0.8327(12) -0.1999(5) 0.5548(6) 0.0937 1.0000 Uiso H91 h 0.909(1) 0.3977(5) 0.7866(6) 0.0819 1.0000 Uiso H101 h 0.823(1) 0.4519(5) 0.9402(6) 0.0807 1.0000 Uiso H111 h 0.748(1) 0.3378(5) 1.0624(6) 0.0854 1.0000 Uiso H121 h 0.773(1) 0.1658(5) 1.0354(6) 0.0851 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 0.055(1) 0.0792(12) 0.0798(11) -0.0026(9) 0.0060(8) -0.0036(8) Cl2 0.059(1) 0.0502(9) 0.1111(14) 0.0064(9) -0.0110(9) 0.0034(7) O1 0.069(3) 0.060(3) 0.091(3) 0.003(2) -0.012(3) 0.009(2) O2 0.067(3) 0.044(2) 0.096(3) 0.000(2) -0.003(2) 0.005(2) O3 0.083(4) 0.056(3) 0.080(3) 0.005(2) 0.003(3) -0.013(2) O4 0.093(4) 0.047(3) 0.080(3) 0.009(2) 0.013(3) -0.006(2) N1 0.063(3) 0.045(3) 0.070(3) 0.005(2) 0.004(3) 0.001(2) C1 0.052(4) 0.050(4) 0.076(4) 0.002(3) -0.006(3) 0.002(3) C2 0.061(4) 0.039(3) 0.069(4) -0.002(3) 0.003(3) -0.002(3) C3 0.056(4) 0.045(3) 0.070(4) -0.003(3) -0.004(3) -0.001(3) C4 0.052(4) 0.045(3) 0.092(5) 0.001(3) -0.003(3) -0.000(3) C5 0.055(4) 0.070(5) 0.111(6) 0.020(4) 0.012(4) 0.006(3) C6 0.086(5) 0.052(4) 0.099(5) -0.003(4) -0.005(4) -0.002(4) C7 0.056(4) 0.048(3) 0.071(4) 0.005(3) 0.001(3) -0.009(3) C8 0.059(4) 0.038(3) 0.079(4) -0.000(3) -0.004(3) 0.000(2) C9 0.073(5) 0.054(4) 0.090(5) 0.003(4) -0.010(4) -0.004(3) C10 0.068(4) 0.048(4) 0.089(5) -0.009(4) -0.008(4) 0.002(3) C11 0.070(5) 0.058(4) 0.089(5) -0.018(4) 0.002(4) 0.009(3) C12 0.064(4) 0.063(4) 0.083(5) -0.007(3) -0.002(4) 0.001(3) C13 0.058(4) 0.040(3) 0.076(4) -0.001(3) -0.004(3) -0.001(3) C14 0.067(4) 0.057(4) 0.067(4) -0.005(3) 0.004(3) 0.003(3) 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 . 1.787(7) yes Cl2 . C3 . 1.770(6) yes O1 . C1 . 1.196(8) yes O2 . C1 . 1.327(8) yes O2 . C4 . 1.490(8) yes O3 . C7 . 1.184(8) yes O4 . C14 . 1.202(8) yes N1 . C2 . 1.441(8) yes N1 . C7 . 1.432(8) yes N1 . C14 . 1.402(9) yes C1 . C2 . 1.566(9) yes C2 . C3 . 1.555(9) yes C3 . C4 . 1.537(9) yes C3 . H31 . 1.000 no C4 . C5 . 1.54(1) yes C4 . C6 . 1.50(1) yes C5 . H51 . 1.000 no C5 . H52 . 1.000 no C5 . H53 . 1.000 no C6 . H61 . 1.000 no C6 . H62 . 1.000 no C6 . H63 . 1.000 no C7 . C8 . 1.49(1) yes C8 . C9 . 1.384(9) yes C8 . C13 . 1.403(9) yes C9 . C10 . 1.353(11) yes C9 . H91 . 1.000 no C10 . C11 . 1.397(11) yes C10 . H101 . 1.000 no C11 . C12 . 1.38(1) yes C11 . H111 . 1.000 no C12 . C13 . 1.39(1) yes C12 . H121 . 1.000 no C13 . C14 . 1.485(9) 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 C1 . O2 . C4 . 114.1(5) yes C2 . N1 . C7 . 124.6(5) yes C2 . N1 . C14 . 123.1(5) yes C7 . N1 . C14 . 112.3(5) yes O1 . C1 . O2 . 123.8(6) yes O1 . C1 . C2 . 125.4(6) yes O2 . C1 . C2 . 110.5(5) yes Cl1 . C2 . N1 . 110.9(4) yes Cl1 . C2 . C1 . 104.1(5) yes N1 . C2 . C1 . 112.4(5) yes Cl1 . C2 . C3 . 109.9(4) yes N1 . C2 . C3 . 117.1(5) yes C1 . C2 . C3 . 101.3(5) yes Cl2 . C3 . C2 . 113.5(4) yes Cl2 . C3 . C4 . 114.1(4) yes C2 . C3 . C4 . 107.3(5) yes Cl2 . C3 . H31 . 102.8(2) no C2 . C3 . H31 . 109.6(3) no C4 . C3 . H31 . 109.4(4) no O2 . C4 . C3 . 102.4(5) yes O2 . C4 . C5 . 107.0(6) yes C3 . C4 . C5 . 115.7(6) yes O2 . C4 . C6 . 106.7(6) yes C3 . C4 . C6 . 112.1(6) yes C5 . C4 . C6 . 111.9(6) yes C4 . C5 . H51 . 109.9(4) no C4 . C5 . H52 . 109.0(4) no H51 . C5 . H52 . 109.476 no C4 . C5 . H53 . 109.5(4) no H51 . C5 . H53 . 109.476 no H52 . C5 . H53 . 109.476 no C4 . C6 . H61 . 109.4(4) no C4 . C6 . H62 . 110.3(4) no H61 . C6 . H62 . 109.476 no C4 . C6 . H63 . 108.7(4) no H61 . C6 . H63 . 109.476 no H62 . C6 . H63 . 109.476 no O3 . C7 . N1 . 126.2(7) yes O3 . C7 . C8 . 129.1(6) yes N1 . C7 . C8 . 104.7(6) yes C7 . C8 . C9 . 131.6(7) yes C7 . C8 . C13 . 108.6(5) yes C9 . C8 . C13 . 119.8(7) yes C8 . C9 . C10 . 119.4(7) yes C8 . C9 . H91 . 119.8(5) no C10 . C9 . H91 . 120.8(4) no C9 . C10 . C11 . 120.8(7) yes C9 . C10 . H101 . 119.6(4) no C11 . C10 . H101 . 119.6(4) no C10 . C11 . C12 . 121.7(7) yes C10 . C11 . H111 . 119.2(4) no C12 . C11 . H111 . 119.2(5) no C11 . C12 . C13 . 117.0(7) yes C11 . C12 . H121 . 121.7(5) no C13 . C12 . H121 . 121.3(4) no C8 . C13 . C12 . 121.3(6) yes C8 . C13 . C14 . 108.7(6) yes C12 . C13 . C14 . 130.0(6) yes O4 . C14 . N1 . 125.2(6) yes O4 . C14 . C13 . 129.0(6) yes N1 . C14 . C13 . 105.7(6) yes