# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_ckl8 _database_code_CSD 191571 #------------------------------------------------------------------------------ _audit_creation_date '2000-08-02' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; 2000-08-02 - Report on C11 H7 Cl2 N O3 by Anthony C. Willis for Connie K. Y. Lee and Christopher J. Easton 2000-08-02 - passes checkcif tests with minor warnings ; #------------------------------------------------------------------------------ _publ_requested_journal ' JCS Perkin 2 ' _publ_requested_category 'FO ' _publ_contact_author_name ' Anthony C. Willis ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' 61 2 6125 4109 ' _publ_contact_author_fax ' 61 2 6125 0750 ' _publ_contact_author_email ' willis@rsc.anu.edu.au ' loop_ _publ_author_name _publ_author_address ' Connie K. Y. Lee ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Christopher J. Easton ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Mariana Gebara-Coghlan ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Leo Radom ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Anthony P. Scott ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Gregory W. Simpson ' ; CSIRO Molecular Science, Bayview Ave, Clayton, Victoria 3168, Australia ; ' Anthony C. Willis ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_section_title ; Substituent effects in isoxazoles: identification of 4-substituted isoxazoles as Michael acceptors ; _publ_section_title_footnote ' ENTER ANY FOOTNOTES TO TITLE ' _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. 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. 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., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Blessing, R. H.; Acta Crystallogr., Section A, 51, 33-37 (1995). Blessing, R. H.; J. Appl. Crystallogr., 30, 421-426 (1997). ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 14.7870(2) _cell_length_b 22.7233(3) _cell_length_c 14.1751(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4763.0(1) _cell_formula_units_Z 16 _cell_measurement_temperature 200.0 _cell_measurement_reflns_used 52594 _cell_measurement_theta_min 4.076 _cell_measurement_theta_max 27.485 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21 ' _symmetry_Int_Tables_number 33 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y,1/2+z' '1/2-x,1/2+y,1/2+z' '1/2+x,1/2-y, +z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 272.09 _chemical_formula_analytical ? _chemical_formula_sum 'C11 H7 Cl2 N O3 ' _chemical_formula_moiety 'C11 H7 Cl2 N O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 2208.00 _exptl_absorpt_coefficient_mu 0.538 # units are mm-1 # Absorption correction _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.895 _exptl_absorpt_correction_T_max 0.955 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) inplemented in maXus (1999) 1 0 0 0.2500 -1 0 0 0.2300 0 1 0 0.0600 0 -1 0 0.0300 0 0 1 0.0400 0 0 -1 0.0700 ; #------------------------------------------------------------------------------ _diffrn_special_details ; CCD data collecting conditions- omega scans of 1.3 deg/frame at rate of 70 sec/frame, crystal-detector distance 30mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more (assuming Friedel's Law). ; _diffrn_ambient_temperature 200.0 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'CCD' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_detector_area_resol_mean ? _diffrn_measurement_method ' omega scans with CCD ' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 69227 _reflns_number_total 5676 _reflns_number_gt 3287 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.06514 _diffrn_reflns_av_sigmaI/netI 0.150 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 176 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 112 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Cl 0 32 0.132 0.159 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N 0 16 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 48 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ 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_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom Cl(132) 0.5832(1) 0.20259(8) 0.0000 0.0805(6) 1.000 . Uani d ? Cl(136) 0.8891(1) 0.23150(7) -0.2000(2) 0.0633(5) 1.000 . Uani d ? Cl(232) 0.6284(1) 0.45169(6) 0.3643(2) 0.0625(5) 1.000 . Uani d ? Cl(236) 0.6378(1) 0.22456(7) 0.2560(2) 0.0838(6) 1.000 . Uani d ? Cl(332) 0.4507(1) 0.4243(1) 0.6304(2) 0.1142(8) 1.000 . Uani d ? Cl(336) 0.1270(1) 0.4431(1) 0.4614(2) 0.1184(9) 1.000 . Uani d ? Cl(432) 0.6039(1) -0.16536(7) 0.1069(2) 0.0744(5) 1.000 . Uani d ? Cl(436) 0.6557(1) 0.06188(7) 0.1992(2) 0.0673(5) 1.000 . Uani d ? O(11) 0.8423(3) 0.2735(1) 0.1008(3) 0.060(1) 1.000 . Uani d ? O(21) 0.5675(2) 0.3768(2) 0.0835(3) 0.058(1) 1.000 . Uani d ? O(31) 0.3862(3) 0.4777(2) 0.3348(3) 0.060(1) 1.000 . Uani d ? O(41) 0.5614(3) -0.0834(2) 0.3818(2) 0.052(1) 1.000 . Uani d ? O(141) 0.8217(3) 0.0989(2) -0.0549(3) 0.058(1) 1.000 . Uani d ? O(142) 0.8667(2) 0.0930(1) 0.0953(2) 0.041(1) 1.000 . Uani d ? O(241) 0.8218(2) 0.3821(2) 0.2664(3) 0.048(1) 1.000 . Uani d ? O(242) 0.8389(2) 0.4116(2) 0.1167(3) 0.044(1) 1.000 . Uani d ? O(341) 0.3296(3) 0.3086(2) 0.4966(3) 0.061(1) 1.000 . Uani d ? O(342) 0.3935(2) 0.2983(1) 0.3539(3) 0.048(1) 1.000 . Uani d ? O(441) 0.8172(2) -0.0944(2) 0.2021(3) 0.052(1) 1.000 . Uani d ? O(442) 0.8288(2) -0.1281(1) 0.3510(3) 0.044(1) 1.000 . Uani d ? N(12) 0.7908(3) 0.2801(2) 0.0168(3) 0.056(1) 1.000 . Uani d ? N(22) 0.5497(3) 0.3530(2) 0.1744(3) 0.051(1) 1.000 . Uani d ? N(32) 0.3436(3) 0.4906(2) 0.4223(3) 0.051(1) 1.000 . Uani d ? N(42) 0.5444(3) -0.0613(2) 0.2899(3) 0.049(1) 1.000 . Uani d ? C(13) 0.7836(3) 0.2273(2) -0.0186(3) 0.040(1) 1.000 . Uani d ? C(14) 0.8277(4) 0.1848(2) 0.0389(3) 0.038(1) 1.000 . Uani d ? C(15) 0.8617(4) 0.2164(2) 0.1110(4) 0.051(2) 1.000 . Uani d ? C(23) 0.6265(3) 0.3569(2) 0.2198(3) 0.037(1) 1.000 . Uani d ? C(24) 0.6957(3) 0.3825(2) 0.1625(3) 0.035(1) 1.000 . Uani d ? C(25) 0.6541(4) 0.3939(2) 0.0794(4) 0.045(2) 1.000 . Uani d ? C(33) 0.3298(3) 0.4390(2) 0.4616(3) 0.041(1) 1.000 . Uani d ? C(34) 0.3617(3) 0.3927(2) 0.4042(3) 0.039(1) 1.000 . Uani d ? C(35) 0.3950(4) 0.4199(2) 0.3270(4) 0.048(2) 1.000 . Uani d ? C(43) 0.6221(3) -0.0670(2) 0.2455(3) 0.040(1) 1.000 . Uani d ? C(44) 0.6892(3) -0.0922(2) 0.3039(3) 0.036(1) 1.000 . Uani d ? C(45) 0.6477(4) -0.1012(2) 0.3865(3) 0.043(2) 1.000 . Uani d ? C(131) 0.7318(3) 0.2188(2) -0.1075(3) 0.039(1) 1.000 . Uani d ? C(132) 0.6400(4) 0.2065(2) -0.1060(4) 0.047(2) 1.000 . Uani d ? C(133) 0.5917(4) 0.1983(2) -0.1887(5) 0.056(2) 1.000 . Uani d ? C(134) 0.6349(5) 0.2024(2) -0.2747(4) 0.058(2) 1.000 . Uani d ? C(135) 0.7268(4) 0.2139(2) -0.2786(4) 0.051(2) 1.000 . Uani d ? C(136) 0.7733(3) 0.2211(2) -0.1953(4) 0.041(1) 1.000 . Uani d ? C(141) 0.8377(3) 0.1215(2) 0.0194(3) 0.037(1) 1.000 . Uani d ? C(143) 0.8855(4) 0.0312(2) 0.0831(4) 0.057(2) 1.000 . Uani d ? C(231) 0.6318(3) 0.3366(2) 0.3190(4) 0.038(1) 1.000 . Uani d ? C(232) 0.6335(3) 0.3776(2) 0.3923(4) 0.043(2) 1.000 . Uani d ? C(233) 0.6380(4) 0.3614(3) 0.4854(4) 0.060(2) 1.000 . Uani d ? C(234) 0.6410(4) 0.3031(3) 0.5072(4) 0.070(2) 1.000 . Uani d ? C(235) 0.6397(4) 0.2605(3) 0.4384(5) 0.068(2) 1.000 . Uani d ? C(236) 0.6353(4) 0.2781(2) 0.3437(4) 0.050(2) 1.000 . Uani d ? C(241) 0.7900(3) 0.3918(2) 0.1893(4) 0.037(1) 1.000 . Uani d ? C(243) 0.9343(4) 0.4183(3) 0.1343(4) 0.058(2) 1.000 . Uani d ? C(331) 0.2852(4) 0.4371(2) 0.5547(4) 0.043(2) 1.000 . Uani d ? C(332) 0.3340(5) 0.4317(3) 0.6366(4) 0.064(2) 1.000 . Uani d ? C(333) 0.2919(8) 0.4314(3) 0.7247(4) 0.105(3) 1.000 . Uani d ? C(334) 0.201(1) 0.4344(3) 0.7303(7) 0.129(4) 1.000 . Uani d ? C(335) 0.1499(6) 0.4393(3) 0.6503(8) 0.108(3) 1.000 . Uani d ? C(336) 0.1921(4) 0.4399(3) 0.5625(5) 0.066(2) 1.000 . Uani d ? C(341) 0.3587(3) 0.3296(2) 0.4253(4) 0.043(2) 1.000 . Uani d ? C(343) 0.3948(4) 0.2348(2) 0.3678(4) 0.060(2) 1.000 . Uani d ? C(431) 0.6267(3) -0.0499(2) 0.1445(4) 0.040(2) 1.000 . Uani d ? C(432) 0.6173(4) -0.0925(2) 0.0744(4) 0.048(2) 1.000 . Uani d ? C(433) 0.6196(4) -0.0788(3) -0.0202(4) 0.059(2) 1.000 . Uani d ? C(434) 0.6294(4) -0.0212(3) -0.0460(4) 0.062(2) 1.000 . Uani d ? C(435) 0.6397(4) 0.0226(3) 0.0200(5) 0.060(2) 1.000 . Uani d ? C(436) 0.6390(3) 0.0076(2) 0.1161(4) 0.048(2) 1.000 . Uani d ? C(441) 0.7848(4) -0.1039(2) 0.2785(3) 0.039(2) 1.000 . Uani d ? C(443) 0.9240(4) -0.1384(3) 0.3361(4) 0.054(2) 1.000 . Uani d ? H(1) 0.8949 0.2003 0.1621 0.061 1.000 . Uiso c ? H(2) 0.7570 0.2168 -0.3375 0.061 1.000 . Uiso c ? H(3) 0.6016 0.1973 -0.3314 0.069 1.000 . Uiso c ? H(4) 0.5288 0.1898 -0.1862 0.067 1.000 . Uiso c ? H(5) 0.6822 0.4115 0.0260 0.054 1.000 . Uiso c ? H(6) 0.6418 0.2199 0.4546 0.082 1.000 . Uiso c ? H(7) 0.6440 0.2916 0.5715 0.084 1.000 . Uiso c ? H(8) 0.6391 0.3903 0.5337 0.072 1.000 . Uiso c ? H(9) 0.4210 0.4003 0.2744 0.058 1.000 . Uiso c ? H(10) 0.3271 0.4290 0.7805 0.126 1.000 . Uiso c ? H(11) 0.1717 0.4330 0.7901 0.155 1.000 . Uiso c ? H(12) 0.0860 0.4424 0.6544 0.130 1.000 . Uiso c ? H(13) 0.6754 -0.1178 0.4407 0.052 1.000 . Uiso c ? H(14) 0.6472 0.0624 0.0009 0.072 1.000 . Uiso c ? H(15) 0.6291 -0.0112 -0.1111 0.074 1.000 . Uiso c ? H(16) 0.6143 -0.1088 -0.0667 0.071 1.000 . Uiso c ? H(17) 0.9350 0.0265 0.0409 0.068 1.000 . Uiso c ? H(18) 0.8337 0.0121 0.0579 0.068 1.000 . Uiso c ? H(19) 0.9004 0.0142 0.1423 0.068 1.000 . Uiso c ? H(20) 0.9625 0.4351 0.0804 0.070 1.000 . Uiso c ? H(21) 0.9430 0.4433 0.1871 0.070 1.000 . Uiso c ? H(22) 0.9602 0.3809 0.1468 0.070 1.000 . Uiso c ? H(23) 0.3371 0.2221 0.3891 0.072 1.000 . Uiso c ? H(24) 0.4088 0.2159 0.3098 0.072 1.000 . Uiso c ? H(25) 0.4393 0.2250 0.4135 0.072 1.000 . Uiso c ? H(26) 0.9322 -0.1599 0.2792 0.065 1.000 . Uiso c ? H(27) 0.9547 -0.1018 0.3317 0.065 1.000 . Uiso c ? H(28) 0.9477 -0.1604 0.3874 0.065 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl(132) 0.068(1) 0.102(1) 0.072(1) 0.002(1) 0.0255(9) 0.014(1) Cl(136) 0.0484(9) 0.081(1) 0.0608(9) 0.0026(8) 0.0061(7) 0.0142(8) Cl(232) 0.094(1) 0.0477(8) 0.0459(8) -0.0040(8) 0.0054(8) -0.0102(7) Cl(236) 0.111(1) 0.0466(9) 0.094(1) -0.0002(9) 0.023(1) -0.0131(9) Cl(332) 0.101(2) 0.161(2) 0.081(1) -0.071(1) -0.045(1) 0.055(1) Cl(336) 0.055(1) 0.144(2) 0.157(2) 0.016(1) -0.004(1) 0.064(2) Cl(432) 0.128(1) 0.0505(9) 0.0446(8) -0.0045(9) 0.0059(9) -0.0062(7) Cl(436) 0.070(1) 0.0524(9) 0.079(1) -0.0063(8) -0.0089(9) -0.0040(8) O(11) 0.104(3) 0.034(2) 0.043(2) 0.009(2) -0.022(2) -0.007(2) O(21) 0.042(2) 0.100(3) 0.031(2) 0.000(2) -0.002(2) 0.004(2) O(31) 0.094(3) 0.041(2) 0.044(2) 0.003(2) 0.025(2) 0.011(2) O(41) 0.048(2) 0.081(3) 0.029(2) -0.005(2) 0.007(2) -0.002(2) O(141) 0.097(3) 0.042(2) 0.034(2) 0.004(2) -0.016(2) -0.004(2) O(142) 0.058(2) 0.034(2) 0.031(2) 0.010(2) -0.009(2) -0.002(1) O(241) 0.049(2) 0.059(2) 0.035(2) -0.001(2) -0.005(2) 0.002(2) O(242) 0.043(2) 0.057(2) 0.032(2) -0.007(2) 0.004(2) 0.000(2) O(341) 0.091(3) 0.042(2) 0.050(2) -0.009(2) 0.025(2) 0.001(2) O(342) 0.071(3) 0.037(2) 0.036(2) 0.002(2) 0.012(2) -0.001(2) O(441) 0.050(2) 0.074(3) 0.031(2) 0.008(2) 0.007(2) 0.004(2) O(442) 0.048(2) 0.048(2) 0.035(2) 0.010(2) 0.006(2) 0.006(2) N(12) 0.084(3) 0.037(3) 0.046(2) 0.011(2) -0.013(2) -0.003(2) N(22) 0.047(3) 0.076(3) 0.031(2) -0.004(2) 0.000(2) 0.001(2) N(32) 0.069(3) 0.045(3) 0.039(2) 0.006(2) 0.012(2) 0.005(2) N(42) 0.048(3) 0.067(3) 0.032(2) 0.000(2) 0.001(2) 0.003(2) C(13) 0.051(3) 0.035(3) 0.035(3) 0.002(3) -0.001(2) 0.002(2) C(14) 0.050(3) 0.037(3) 0.029(2) 0.003(3) -0.002(2) 0.000(2) C(15) 0.071(4) 0.038(3) 0.044(3) 0.009(3) -0.013(3) -0.001(3) C(23) 0.039(3) 0.035(3) 0.036(3) -0.001(2) 0.002(2) -0.005(2) C(24) 0.045(3) 0.036(3) 0.025(2) 0.004(2) 0.006(2) -0.004(2) C(25) 0.047(4) 0.060(4) 0.029(3) 0.000(3) 0.005(2) -0.003(2) C(33) 0.047(3) 0.039(3) 0.037(3) -0.003(3) 0.003(2) 0.001(2) C(34) 0.049(3) 0.039(3) 0.028(2) 0.002(2) -0.001(2) 0.003(2) C(35) 0.069(4) 0.042(3) 0.033(3) 0.007(3) 0.007(3) 0.004(2) C(43) 0.046(3) 0.045(3) 0.027(2) -0.003(3) 0.002(2) -0.004(2) C(44) 0.042(3) 0.040(3) 0.027(2) -0.002(2) 0.001(2) -0.004(2) C(45) 0.045(4) 0.054(3) 0.031(3) -0.003(3) -0.002(2) 0.000(2) C(131) 0.044(3) 0.035(3) 0.039(3) 0.006(2) -0.004(2) 0.004(2) C(132) 0.048(4) 0.042(3) 0.051(3) 0.004(3) 0.000(3) 0.008(3) C(133) 0.044(3) 0.054(4) 0.070(4) 0.001(3) -0.006(3) 0.009(3) C(134) 0.061(5) 0.049(3) 0.063(4) 0.003(3) -0.026(3) 0.002(3) C(135) 0.070(5) 0.041(3) 0.041(3) 0.008(3) -0.005(3) 0.004(2) C(136) 0.046(3) 0.035(3) 0.040(3) 0.005(2) -0.001(3) 0.007(2) C(141) 0.045(3) 0.032(3) 0.033(3) 0.002(2) -0.005(2) 0.000(2) C(143) 0.087(5) 0.038(3) 0.046(3) 0.016(3) -0.007(3) 0.000(3) C(231) 0.039(3) 0.042(3) 0.032(3) 0.000(2) 0.004(2) -0.002(2) C(232) 0.046(3) 0.052(3) 0.032(3) -0.004(3) -0.002(2) 0.001(2) C(233) 0.061(4) 0.086(5) 0.034(3) -0.003(3) 0.003(3) 0.004(3) C(234) 0.074(5) 0.095(5) 0.041(3) 0.004(4) -0.001(3) 0.022(4) C(235) 0.064(4) 0.069(5) 0.072(4) 0.008(3) 0.011(3) 0.037(4) C(236) 0.049(3) 0.042(3) 0.058(3) -0.001(3) 0.008(3) 0.001(3) C(241) 0.046(3) 0.033(3) 0.030(3) 0.003(2) 0.000(2) 0.002(2) C(243) 0.046(4) 0.072(4) 0.056(3) -0.012(3) 0.007(3) 0.000(3) C(331) 0.061(4) 0.032(3) 0.037(3) -0.002(3) 0.007(3) -0.002(2) C(332) 0.101(5) 0.049(4) 0.043(3) -0.030(4) -0.002(3) 0.003(3) C(333) 0.22(1) 0.064(5) 0.032(4) -0.071(6) 0.023(5) -0.004(3) C(334) 0.26(1) 0.039(4) 0.090(7) -0.021(7) 0.110(9) -0.004(4) C(335) 0.124(8) 0.056(5) 0.144(8) 0.031(5) 0.102(7) 0.026(5) C(336) 0.071(5) 0.051(4) 0.076(4) 0.016(3) 0.031(4) 0.007(3) C(341) 0.047(3) 0.046(3) 0.035(3) -0.004(3) 0.004(2) -0.001(3) C(343) 0.083(4) 0.035(3) 0.062(4) 0.001(3) 0.010(3) -0.004(3) C(431) 0.039(3) 0.049(3) 0.032(3) 0.003(2) 0.004(2) 0.007(2) C(432) 0.061(4) 0.051(3) 0.031(3) 0.005(3) 0.007(3) 0.002(3) C(433) 0.068(4) 0.071(4) 0.039(3) 0.006(3) 0.006(3) 0.003(3) C(434) 0.059(4) 0.084(5) 0.043(3) 0.002(3) 0.005(3) 0.022(3) C(435) 0.061(4) 0.055(4) 0.063(4) -0.003(3) 0.005(3) 0.025(3) C(436) 0.035(3) 0.052(3) 0.056(3) 0.001(3) -0.002(3) -0.001(3) C(441) 0.054(4) 0.034(3) 0.029(3) 0.000(2) 0.001(2) -0.003(2) C(443) 0.047(4) 0.072(4) 0.044(3) 0.019(3) -0.001(3) 0.006(3) #------------------------------------------------------------------------------ _refine_special_details ; \s^2^(Fo) is the larger of the value from averaging of equivalent reflections or counting statistics. Friedel mates have been excluded from the least-squares refinement, but are used in the absolute structure determination. H atoms were included in the refinement at idealized positions (methyl groups oriented to best-fit the peaks in an inner-data difference map) which were frequently recalculated. There are four independent molecules of C11 H7 Cl2 N O3 in the crystallographic asymmetric unit. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1/[\s^2^(Fo)] ; _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; Although this crystal has a polar spacegroup, IT IS STILL RACEMIC. The absolute structure of the CRYSTAL has been determined by relative refinement (this model gives R = 0.0379, wR = 0.0374, GOF = 0.97 -- whereas the model with inverted coordinates gives R = 0.0386, wR = 0.0383, GOF = 0.99). In addition, comparison of Fobs of Friedel pairs with the largest Fcalc differences, show 70 in agreement with the present model and 12 in disagreement (the strongest 7 all in agreement). ; _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3287 _refine_ls_number_parameters 612 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_all 0.0495 _refine_ls_wR_factor_ref 0.0374 _refine_ls_goodness_of_fit_all 0.934 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_shift/su_max 0.0080 _refine_ls_shift/su_mean 0.0009 _refine_diff_density_min -0.41 _refine_diff_density_max 0.28 #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl(132) C(132) 1.724(5) . . yes Cl(136) C(136) 1.729(5) . . yes Cl(232) C(232) 1.731(5) . . yes Cl(236) C(236) 1.740(5) . . yes Cl(332) C(332) 1.735(7) . . yes Cl(336) C(336) 1.727(7) . . yes Cl(432) C(432) 1.730(6) . . yes Cl(436) C(436) 1.723(5) . . yes O(11) N(12) 1.422(5) . . yes O(11) C(15) 1.337(6) . . yes O(21) N(22) 1.422(5) . . yes O(21) C(25) 1.339(6) . . yes O(31) N(32) 1.423(5) . . yes O(31) C(35) 1.324(6) . . yes O(41) N(42) 1.419(5) . . yes O(41) C(45) 1.340(6) . . yes O(141) C(141) 1.196(5) . . yes O(142) C(141) 1.327(5) . . yes O(142) C(143) 1.442(6) . . yes O(241) C(241) 1.211(5) . . yes O(242) C(241) 1.336(5) . . yes O(242) C(243) 1.440(7) . . yes O(341) C(341) 1.198(6) . . yes O(342) C(341) 1.339(6) . . yes O(342) C(343) 1.456(6) . . yes O(441) C(441) 1.204(5) . . yes O(442) C(441) 1.335(5) . . yes O(442) C(443) 1.442(6) . . yes N(12) C(13) 1.303(6) . . yes N(22) C(23) 1.309(6) . . yes N(32) C(33) 1.314(6) . . yes N(42) C(43) 1.316(6) . . yes C(13) C(14) 1.423(7) . . yes C(13) C(131) 1.488(6) . . yes C(14) C(15) 1.345(7) . . yes C(14) C(141) 1.472(7) . . yes C(15) H(1) 0.95 . . no C(23) C(24) 1.431(6) . . yes C(23) C(231) 1.480(7) . . yes C(24) C(25) 1.354(7) . . yes C(24) C(241) 1.462(7) . . yes C(25) H(5) 0.95 . . no C(33) C(34) 1.411(7) . . yes C(33) C(331) 1.477(7) . . yes C(34) C(35) 1.350(7) . . yes C(34) C(341) 1.464(7) . . yes C(35) H(9) 0.95 . . no C(43) C(44) 1.413(7) . . yes C(43) C(431) 1.485(6) . . yes C(44) C(45) 1.338(7) . . yes C(44) C(441) 1.482(7) . . yes C(45) H(13) 0.95 . . no C(131) C(132) 1.386(7) . . yes C(131) C(136) 1.389(7) . . yes C(132) C(133) 1.385(7) . . yes C(133) C(134) 1.380(8) . . yes C(133) H(4) 0.95 . . no C(134) C(135) 1.383(8) . . yes C(134) H(3) 0.95 . . no C(135) C(136) 1.376(7) . . yes C(135) H(2) 0.95 . . no C(143) H(17) 0.95 . . no C(143) H(18) 0.95 . . no C(143) H(19) 0.95 . . no C(231) C(232) 1.395(7) . . yes C(231) C(236) 1.377(7) . . yes C(232) C(233) 1.372(7) . . yes C(233) C(234) 1.361(9) . . yes C(233) H(8) 0.95 . . no C(234) C(235) 1.374(9) . . yes C(234) H(7) 0.95 . . no C(235) C(236) 1.402(8) . . yes C(235) H(6) 0.95 . . no C(243) H(20) 0.95 . . no C(243) H(21) 0.95 . . no C(243) H(22) 0.95 . . no C(331) C(332) 1.373(8) . . yes C(331) C(336) 1.382(8) . . yes C(332) C(333) 1.395(9) . . yes C(333) C(334) 1.35(1) . . yes C(333) H(10) 0.95 . . no C(334) C(335) 1.36(1) . . yes C(334) H(11) 0.95 . . no C(335) C(336) 1.39(1) . . yes C(335) H(12) 0.95 . . no C(343) H(23) 0.95 . . no C(343) H(24) 0.95 . . no C(343) H(25) 0.95 . . no C(431) C(432) 1.395(7) . . yes C(431) C(436) 1.379(7) . . yes C(432) C(433) 1.377(7) . . yes C(433) C(434) 1.366(9) . . yes C(433) H(16) 0.95 . . no C(434) C(435) 1.375(9) . . yes C(434) H(15) 0.95 . . no C(435) C(436) 1.405(7) . . yes C(435) H(14) 0.95 . . no C(443) H(26) 0.95 . . no C(443) H(27) 0.95 . . no C(443) H(28) 0.95 . . no #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N(12) O(11) C(15) 107.8(3) . . . yes N(22) O(21) C(25) 109.1(4) . . . yes N(32) O(31) C(35) 108.7(4) . . . yes N(42) O(41) C(45) 108.7(4) . . . yes C(141) O(142) C(143) 116.2(4) . . . yes C(241) O(242) C(243) 115.6(4) . . . yes C(341) O(342) C(343) 115.4(4) . . . yes C(441) O(442) C(443) 115.4(4) . . . yes O(11) N(12) C(13) 105.6(4) . . . yes O(21) N(22) C(23) 105.0(4) . . . yes O(31) N(32) C(33) 104.7(4) . . . yes O(41) N(42) C(43) 104.4(4) . . . yes N(12) C(13) C(14) 111.5(4) . . . yes N(12) C(13) C(131) 119.2(4) . . . yes C(14) C(13) C(131) 129.3(4) . . . yes C(13) C(14) C(15) 104.1(4) . . . yes C(13) C(14) C(141) 127.0(4) . . . yes C(15) C(14) C(141) 128.8(4) . . . yes O(11) C(15) C(14) 110.9(4) . . . yes O(11) C(15) H(1) 124.6 . . . no C(14) C(15) H(1) 124.5 . . . no N(22) C(23) C(24) 111.6(4) . . . yes N(22) C(23) C(231) 119.5(4) . . . yes C(24) C(23) C(231) 128.9(4) . . . yes C(23) C(24) C(25) 104.3(4) . . . yes C(23) C(24) C(241) 126.4(4) . . . yes C(25) C(24) C(241) 129.2(4) . . . yes O(21) C(25) C(24) 109.9(4) . . . yes O(21) C(25) H(5) 125.0 . . . no C(24) C(25) H(5) 125.1 . . . no N(32) C(33) C(34) 111.7(4) . . . yes N(32) C(33) C(331) 118.2(4) . . . yes C(34) C(33) C(331) 130.1(5) . . . yes C(33) C(34) C(35) 104.3(4) . . . yes C(33) C(34) C(341) 127.0(4) . . . yes C(35) C(34) C(341) 128.7(5) . . . yes O(31) C(35) C(34) 110.6(4) . . . yes O(31) C(35) H(9) 124.7 . . . no C(34) C(35) H(9) 124.7 . . . no N(42) C(43) C(44) 112.0(4) . . . yes N(42) C(43) C(431) 118.3(5) . . . yes C(44) C(43) C(431) 129.7(5) . . . yes C(43) C(44) C(45) 104.6(4) . . . yes C(43) C(44) C(441) 126.9(4) . . . yes C(45) C(44) C(441) 128.5(5) . . . yes O(41) C(45) C(44) 110.4(4) . . . yes O(41) C(45) H(13) 124.8 . . . no C(44) C(45) H(13) 124.8 . . . no C(13) C(131) C(132) 121.1(4) . . . yes C(13) C(131) C(136) 121.8(4) . . . yes C(132) C(131) C(136) 117.0(4) . . . yes Cl(132) C(132) C(131) 120.1(4) . . . yes Cl(132) C(132) C(133) 118.7(4) . . . yes C(131) C(132) C(133) 121.3(5) . . . yes C(132) C(133) C(134) 120.0(5) . . . yes C(132) C(133) H(4) 120.0 . . . no C(134) C(133) H(4) 120.0 . . . no C(133) C(134) C(135) 120.2(5) . . . yes C(133) C(134) H(3) 119.9 . . . no C(135) C(134) H(3) 119.9 . . . no C(134) C(135) C(136) 118.7(5) . . . yes C(134) C(135) H(2) 120.7 . . . no C(136) C(135) H(2) 120.7 . . . no Cl(136) C(136) C(131) 118.5(4) . . . yes Cl(136) C(136) C(135) 118.6(4) . . . yes C(131) C(136) C(135) 122.9(5) . . . yes O(141) C(141) O(142) 124.6(4) . . . yes O(141) C(141) C(14) 124.4(4) . . . yes O(142) C(141) C(14) 111.0(4) . . . yes O(142) C(143) H(17) 109.5 . . . no O(142) C(143) H(18) 109.5 . . . no O(142) C(143) H(19) 109.5 . . . no H(17) C(143) H(18) 109.4 . . . no H(17) C(143) H(19) 109.5 . . . no H(18) C(143) H(19) 109.5 . . . no C(23) C(231) C(232) 120.0(4) . . . yes C(23) C(231) C(236) 123.0(5) . . . yes C(232) C(231) C(236) 117.0(4) . . . yes Cl(232) C(232) C(231) 118.5(4) . . . yes Cl(232) C(232) C(233) 118.9(4) . . . yes C(231) C(232) C(233) 122.5(5) . . . yes C(232) C(233) C(234) 118.8(6) . . . yes C(232) C(233) H(8) 120.6 . . . no C(234) C(233) H(8) 120.6 . . . no C(233) C(234) C(235) 121.6(5) . . . yes C(233) C(234) H(7) 119.2 . . . no C(235) C(234) H(7) 119.2 . . . no C(234) C(235) C(236) 118.6(5) . . . yes C(234) C(235) H(6) 120.7 . . . no C(236) C(235) H(6) 120.7 . . . no Cl(236) C(236) C(231) 119.6(4) . . . yes Cl(236) C(236) C(235) 118.9(5) . . . yes C(231) C(236) C(235) 121.5(5) . . . yes O(241) C(241) O(242) 123.2(5) . . . yes O(241) C(241) C(24) 125.4(4) . . . yes O(242) C(241) C(24) 111.4(4) . . . yes O(242) C(243) H(20) 109.5 . . . no O(242) C(243) H(21) 109.5 . . . no O(242) C(243) H(22) 109.5 . . . no H(20) C(243) H(21) 109.5 . . . no H(20) C(243) H(22) 109.4 . . . no H(21) C(243) H(22) 109.5 . . . no C(33) C(331) C(332) 121.6(5) . . . yes C(33) C(331) C(336) 121.0(5) . . . yes C(332) C(331) C(336) 117.5(5) . . . yes Cl(332) C(332) C(331) 119.3(5) . . . yes Cl(332) C(332) C(333) 119.3(6) . . . yes C(331) C(332) C(333) 121.5(7) . . . yes C(332) C(333) C(334) 119.8(8) . . . yes C(332) C(333) H(10) 120.0 . . . no C(334) C(333) H(10) 120.1 . . . no C(333) C(334) C(335) 120.2(7) . . . yes C(333) C(334) H(11) 119.9 . . . no C(335) C(334) H(11) 119.9 . . . no C(334) C(335) C(336) 119.9(9) . . . yes C(334) C(335) H(12) 120.1 . . . no C(336) C(335) H(12) 120.0 . . . no Cl(336) C(336) C(331) 119.4(5) . . . yes Cl(336) C(336) C(335) 119.5(7) . . . yes C(331) C(336) C(335) 121.1(7) . . . yes O(341) C(341) O(342) 124.3(5) . . . yes O(341) C(341) C(34) 125.0(5) . . . yes O(342) C(341) C(34) 110.7(4) . . . yes O(342) C(343) H(23) 109.5 . . . no O(342) C(343) H(24) 109.5 . . . no O(342) C(343) H(25) 109.5 . . . no H(23) C(343) H(24) 109.5 . . . no H(23) C(343) H(25) 109.5 . . . no H(24) C(343) H(25) 109.5 . . . no C(43) C(431) C(432) 120.1(4) . . . yes C(43) C(431) C(436) 122.4(5) . . . yes C(432) C(431) C(436) 117.5(4) . . . yes Cl(432) C(432) C(431) 119.0(4) . . . yes Cl(432) C(432) C(433) 118.6(4) . . . yes C(431) C(432) C(433) 122.4(5) . . . yes C(432) C(433) C(434) 118.7(6) . . . yes C(432) C(433) H(16) 120.7 . . . no C(434) C(433) H(16) 120.6 . . . no C(433) C(434) C(435) 121.6(5) . . . yes C(433) C(434) H(15) 119.2 . . . no C(435) C(434) H(15) 119.2 . . . no C(434) C(435) C(436) 118.9(5) . . . yes C(434) C(435) H(14) 120.5 . . . no C(436) C(435) H(14) 120.6 . . . no Cl(436) C(436) C(431) 119.9(4) . . . yes Cl(436) C(436) C(435) 119.2(5) . . . yes C(431) C(436) C(435) 120.9(5) . . . yes O(441) C(441) O(442) 125.0(5) . . . yes O(441) C(441) C(44) 124.5(4) . . . yes O(442) C(441) C(44) 110.6(4) . . . yes O(442) C(443) H(26) 109.5 . . . no O(442) C(443) H(27) 109.5 . . . no O(442) C(443) H(28) 109.5 . . . no H(26) C(443) H(27) 109.4 . . . no H(26) C(443) H(28) 109.5 . . . no H(27) C(443) H(28) 109.5 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl(136) C(133) 3.398(6) . 4 no Cl(136) C(443) 3.519(5) . 2_754 no Cl(232) C(333) 3.517(7) . 2_664 no Cl(232) C(35) 3.566(6) . . no Cl(232) C(143) 3.595(5) . 3_655 no Cl(332) C(143) 3.495(6) . 3_655 no Cl(336) O(41) 3.517(4) . 4_455 no Cl(436) C(243) 3.431(6) . 4_455 no Cl(436) O(142) 3.522(4) . . no O(11) C(241) 3.065(6) . . no O(11) O(242) 3.146(5) . . no O(11) C(24) 3.406(6) . . no O(11) O(241) 3.419(5) . . no O(11) C(243) 3.592(7) . . no O(21) O(142) 3.052(5) . 4_455 no O(21) C(143) 3.408(7) . 4_455 no O(21) C(141) 3.518(6) . 4_455 no O(21) C(443) 3.526(6) . 3_654 no O(31) C(441) 3.334(6) . 4_455 no O(31) O(441) 3.409(5) . 4_455 no O(31) O(442) 3.529(5) . 4_455 no O(31) C(143) 3.574(6) . 4_455 no O(41) C(243) 3.579(7) . 3_645 no O(41) C(133) 3.598(7) . 2_655 no O(141) C(333) 3.230(7) . 4_554 no O(141) C(435) 3.372(7) . . no O(142) N(22) 3.175(5) . 4 no O(142) C(35) 3.324(6) . 4 no O(241) C(343) 3.207(7) . 4 no O(241) C(433) 3.269(6) . 3_655 no O(241) C(434) 3.524(8) . 3_655 no O(242) C(45) 3.282(5) . 3_654 no O(242) N(12) 3.383(5) . . no O(242) C(335) 3.425(8) . 2_664 no O(242) C(336) 3.491(7) . 2_664 no O(341) C(235) 3.320(7) . 4_455 no O(341) C(135) 3.569(6) . 4_456 no O(342) C(15) 3.492(6) . 4_455 no O(441) C(233) 3.299(6) . 3_644 no O(441) C(143) 3.466(7) . . no O(442) C(25) 3.285(6) . 3_645 no O(442) N(32) 3.291(5) . 4 no N(12) C(45) 3.394(7) . 3_654 no N(12) C(25) 3.401(7) . . no N(12) C(24) 3.416(6) . . no N(12) C(241) 3.525(6) . . no N(22) C(15) 3.319(7) . 4_455 no N(22) C(35) 3.497(7) . . no N(32) C(441) 3.398(6) . 4_455 no N(32) C(25) 3.441(7) . 2_665 no N(42) C(335) 3.489(8) . 3_544 no C(134) C(334) 3.26(1) . 4_554 no C(134) C(335) 3.398(9) . 4_554 no C(135) C(334) 3.393(9) . 4_554 no C(135) C(333) 3.438(8) . 4_554 no C(243) C(436) 3.473(7) . 4 no C(243) C(335) 3.474(9) . 2_664 no #------------------------------------------------------------------------------ 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 Cl(132) C(132) C(131) C(13) . . . . 1.5(6) no Cl(132) C(132) C(131) C(136) . . . . 179.8(4) no Cl(132) C(132) C(133) C(134) . . . . 178.6(5) no Cl(136) C(136) C(131) C(13) . . . . 2.3(6) no Cl(136) C(136) C(131) C(132) . . . . -175.9(3) no Cl(136) C(136) C(135) C(134) . . . . 176.6(4) no Cl(232) C(232) C(231) C(23) . . . . 0.5(6) no Cl(232) C(232) C(231) C(236) . . . . -179.6(4) no Cl(232) C(232) C(233) C(234) . . . . 179.3(5) no Cl(236) C(236) C(231) C(23) . . . . 2.4(7) no Cl(236) C(236) C(231) C(232) . . . . -177.6(4) no Cl(236) C(236) C(235) C(234) . . . . 177.7(5) no Cl(332) C(332) C(331) C(33) . . . . -2.2(7) no Cl(332) C(332) C(331) C(336) . . . . 176.8(4) no Cl(332) C(332) C(333) C(334) . . . . -177.0(6) no Cl(336) C(336) C(331) C(33) . . . . 2.1(7) no Cl(336) C(336) C(331) C(332) . . . . -176.9(4) no Cl(336) C(336) C(335) C(334) . . . . 177.4(6) no Cl(432) C(432) C(431) C(43) . . . . -2.0(7) no Cl(432) C(432) C(431) C(436) . . . . 178.8(4) no Cl(432) C(432) C(433) C(434) . . . . 179.4(5) no Cl(436) C(436) C(431) C(43) . . . . 3.6(7) no Cl(436) C(436) C(431) C(432) . . . . -177.3(4) no Cl(436) C(436) C(435) C(434) . . . . 177.8(4) no O(11) N(12) C(13) C(14) . . . . 0.5(6) no O(11) N(12) C(13) C(131) . . . . 179.3(4) no O(11) C(15) C(14) C(13) . . . . -0.6(6) no O(11) C(15) C(14) C(141) . . . . 176.1(5) no O(21) N(22) C(23) C(24) . . . . -0.1(5) no O(21) N(22) C(23) C(231) . . . . 178.9(4) no O(21) C(25) C(24) C(23) . . . . -0.5(6) no O(21) C(25) C(24) C(241) . . . . 177.7(5) no O(31) N(32) C(33) C(34) . . . . 0.3(6) no O(31) N(32) C(33) C(331) . . . . -179.6(4) no O(31) C(35) C(34) C(33) . . . . 0.7(6) no O(31) C(35) C(34) C(341) . . . . -179.3(5) no O(41) N(42) C(43) C(44) . . . . 0.3(6) no O(41) N(42) C(43) C(431) . . . . 177.5(4) no O(41) C(45) C(44) C(43) . . . . 0.0(6) no O(41) C(45) C(44) C(441) . . . . 178.2(4) no O(141) C(141) O(142) C(143) . . . . 4.4(7) no O(141) C(141) C(14) C(13) . . . . 12.1(8) no O(141) C(141) C(14) C(15) . . . . -163.9(6) no O(142) C(141) C(14) C(13) . . . . -167.9(5) no O(142) C(141) C(14) C(15) . . . . 16.1(7) no O(241) C(241) O(242) C(243) . . . . 2.9(7) no O(241) C(241) C(24) C(23) . . . . -4.7(8) no O(241) C(241) C(24) C(25) . . . . 177.6(5) no O(242) C(241) C(24) C(23) . . . . 174.2(4) no O(242) C(241) C(24) C(25) . . . . -3.6(7) no O(341) C(341) O(342) C(343) . . . . -0.3(8) no O(341) C(341) C(34) C(33) . . . . -1.6(9) no O(341) C(341) C(34) C(35) . . . . 178.4(5) no O(342) C(341) C(34) C(33) . . . . 178.7(5) no O(342) C(341) C(34) C(35) . . . . -1.2(8) no O(441) C(441) O(442) C(443) . . . . 5.3(7) no O(441) C(441) C(44) C(43) . . . . -2.0(8) no O(441) C(441) C(44) C(45) . . . . -179.8(5) no O(442) C(441) C(44) C(43) . . . . 180.0(4) no O(442) C(441) C(44) C(45) . . . . 2.2(7) no N(12) O(11) C(15) C(14) . . . . 0.9(6) no N(12) C(13) C(14) C(15) . . . . 0.0(6) no N(12) C(13) C(14) C(141) . . . . -176.8(5) no N(12) C(13) C(131) C(132) . . . . -90.5(6) no N(12) C(13) C(131) C(136) . . . . 91.3(6) no N(22) O(21) C(25) C(24) . . . . 0.4(6) no N(22) C(23) C(24) C(25) . . . . 0.3(6) no N(22) C(23) C(24) C(241) . . . . -177.9(4) no N(22) C(23) C(231) C(232) . . . . -103.9(6) no N(22) C(23) C(231) C(236) . . . . 76.2(7) no N(32) O(31) C(35) C(34) . . . . -0.6(6) no N(32) C(33) C(34) C(35) . . . . -0.6(6) no N(32) C(33) C(34) C(341) . . . . 179.4(5) no N(32) C(33) C(331) C(332) . . . . -98.4(6) no N(32) C(33) C(331) C(336) . . . . 82.7(7) no N(42) O(41) C(45) C(44) . . . . 0.2(6) no N(42) C(43) C(44) C(45) . . . . -0.2(6) no N(42) C(43) C(44) C(441) . . . . -178.5(4) no N(42) C(43) C(431) C(432) . . . . -96.4(6) no N(42) C(43) C(431) C(436) . . . . 82.7(6) no C(13) N(12) O(11) C(15) . . . . -0.9(6) no C(13) C(131) C(132) C(133) . . . . -179.7(5) no C(13) C(131) C(136) C(135) . . . . -179.3(5) no C(14) C(13) C(131) C(132) . . . . 88.0(7) no C(14) C(13) C(131) C(136) . . . . -90.2(7) no C(14) C(141) O(142) C(143) . . . . -175.6(4) no C(15) C(14) C(13) C(131) . . . . -178.6(5) no C(23) N(22) O(21) C(25) . . . . -0.2(5) no C(23) C(231) C(232) C(233) . . . . 179.7(5) no C(23) C(231) C(236) C(235) . . . . -179.6(5) no C(24) C(23) C(231) C(232) . . . . 74.9(7) no C(24) C(23) C(231) C(236) . . . . -105.1(6) no C(24) C(241) O(242) C(243) . . . . -176.0(4) no C(25) C(24) C(23) C(231) . . . . -178.5(5) no C(33) N(32) O(31) C(35) . . . . 0.2(6) no C(33) C(331) C(332) C(333) . . . . 178.5(5) no C(33) C(331) C(336) C(335) . . . . -178.8(6) no C(34) C(33) C(331) C(332) . . . . 81.8(7) no C(34) C(33) C(331) C(336) . . . . -97.1(7) no C(34) C(341) O(342) C(343) . . . . 179.4(4) no C(35) C(34) C(33) C(331) . . . . 179.2(5) no C(43) N(42) O(41) C(45) . . . . -0.3(5) no C(43) C(431) C(432) C(433) . . . . 178.9(5) no C(43) C(431) C(436) C(435) . . . . -177.7(5) no C(44) C(43) C(431) C(432) . . . . 80.2(7) no C(44) C(43) C(431) C(436) . . . . -100.7(7) no C(44) C(441) O(442) C(443) . . . . -176.7(4) no C(45) C(44) C(43) C(431) . . . . -177.0(5) no C(131) C(13) C(14) C(141) . . . . 4.6(9) no C(131) C(132) C(133) C(134) . . . . -0.1(8) no C(131) C(136) C(135) C(134) . . . . -1.7(7) no C(132) C(131) C(136) C(135) . . . . 2.4(7) no C(132) C(133) C(134) C(135) . . . . 0.9(8) no C(133) C(132) C(131) C(136) . . . . -1.5(7) no C(133) C(134) C(135) C(136) . . . . 0.0(8) no C(231) C(23) C(24) C(241) . . . . 3.2(8) no C(231) C(232) C(233) C(234) . . . . 0.0(9) no C(231) C(236) C(235) C(234) . . . . -0.4(9) no C(232) C(231) C(236) C(235) . . . . 0.5(8) no C(232) C(233) C(234) C(235) . . . . 0(1) no C(233) C(232) C(231) C(236) . . . . -0.3(8) no C(233) C(234) C(235) C(236) . . . . 0(1) no C(331) C(33) C(34) C(341) . . . . -0.7(9) no C(331) C(332) C(333) C(334) . . . . 2(1) no C(331) C(336) C(335) C(334) . . . . -2(1) no C(332) C(331) C(336) C(335) . . . . 2.2(9) no C(332) C(333) C(334) C(335) . . . . -2(1) no C(333) C(332) C(331) C(336) . . . . -2.5(8) no C(333) C(334) C(335) C(336) . . . . 1(1) no C(431) C(43) C(44) C(441) . . . . 4.7(8) no C(431) C(432) C(433) C(434) . . . . -1.4(9) no C(431) C(436) C(435) C(434) . . . . -1.0(8) no C(432) C(431) C(436) C(435) . . . . 1.5(8) no C(432) C(433) C(434) C(435) . . . . 1.9(9) no C(433) C(432) C(431) C(436) . . . . -0.3(8) no C(433) C(434) C(435) C(436) . . . . -0.8(9) no #------------------------------------------------------------------------------ _geom_special_details ; Table of Least-Squares Planes #----------------------------- #------------- Plane number 1 --------------- Atoms Defining Plane Distance esd O(11) ( 1) 0.0035 0.0042 N(12) ( 1) -0.0040 0.0050 C(13) ( 1) 0.0021 0.0051 C(14) ( 1) 0.0011 0.0051 C(15) ( 1) -0.0056 0.0059 Additional Atoms Distance C(131) ( 1) -0.0193 C(141) ( 1) 0.0728 Mean deviation from plane is 0.0033 angstroms Chi-squared: 2.6 #------------- Plane number 2 --------------- Atoms Defining Plane Distance esd C(131) ( 1) -0.0099 0.0044 C(132) ( 1) 0.0036 0.0051 C(133) ( 1) 0.0067 0.0055 C(134) ( 1) -0.0067 0.0055 C(135) ( 1) -0.0038 0.0050 C(136) ( 1) 0.0118 0.0045 Additional Atoms Distance C(13) ( 1) -0.0068 Cl(132 ( 1) -0.0156 Cl(136 ( 1) 0.1054 Mean deviation from plane is 0.0071 angstroms Chi-squared: 14.8 Dihedral angles between least-squares planes plane plane angle 2 1 89.42 #------------- Plane number 3 --------------- Atoms Defining Plane Distance esd O(141) ( 1) 0.0000 0.0042 O(142) ( 1) 0.0000 0.0034 C(14) ( 1) 0.0000 0.0052 C(141) ( 1) 0.0000 0.0049 Additional Atoms Distance C(13) ( 1) -0.2379 C(15) ( 1) 0.2912 C(143) ( 1) 0.1000 Mean deviation from plane is 0.0000 angstroms Chi-squared: 0.0 Dihedral angles between least-squares planes plane plane angle 3 1 14.51 3 2 88.71 #------------- Plane number 4 --------------- Atoms Defining Plane Distance esd O(21) ( 1) 0.0013 0.0041 N(22) ( 1) -0.0004 0.0046 C(23) ( 1) -0.0010 0.0049 C(24) ( 1) 0.0018 0.0044 C(25) ( 1) -0.0033 0.0054 Additional Atoms Distance C(231) ( 1) -0.0271 C(241) ( 1) 0.0451 Mean deviation from plane is 0.0016 angstroms Chi-squared: 0.7 Dihedral angles between least-squares planes plane plane angle 4 1 74.63 4 2 21.87 4 3 78.43 #------------- Plane number 5 --------------- Atoms Defining Plane Distance esd C(231) ( 1) -0.0017 0.0045 C(232) ( 1) 0.0008 0.0051 C(233) ( 1) 0.0011 0.0060 C(234) ( 1) -0.0014 0.0064 C(235) ( 1) -0.0012 0.0062 C(236) ( 1) 0.0025 0.0052 Additional Atoms Distance C(23) ( 1) -0.0077 Cl(232 ( 1) -0.0152 Cl(236 ( 1) 0.0632 Mean deviation from plane is 0.0015 angstroms Chi-squared: 0.5 Dihedral angles between least-squares planes plane plane angle 5 1 29.54 5 2 80.44 5 3 16.02 5 4 75.56 #------------- Plane number 6 --------------- Atoms Defining Plane Distance esd O(241) ( 1) 0.0018 0.0036 O(242) ( 1) 0.0010 0.0035 C(24) ( 1) 0.0018 0.0045 C(241) ( 1) -0.0065 0.0046 Additional Atoms Distance C(23) ( 1) 0.1145 C(25) ( 1) -0.0509 C(243) ( 1) 0.0852 Mean deviation from plane is 0.0028 angstroms Chi-squared: 2.4 Dihedral angles between least-squares planes plane plane angle 6 1 79.07 6 2 17.89 6 3 82.34 6 4 4.71 6 5 78.59 #------------- Plane number 7 --------------- Atoms Defining Plane Distance esd O(31) ( 1) 0.0016 0.0042 N(32) ( 1) 0.0003 0.0046 C(33) ( 1) -0.0026 0.0051 C(34) ( 1) 0.0032 0.0049 C(35) ( 1) -0.0046 0.0056 Additional Atoms Distance C(331) ( 1) -0.0138 C(341) ( 1) 0.0141 Mean deviation from plane is 0.0024 angstroms Chi-squared: 1.5 Dihedral angles between least-squares planes plane plane angle 7 1 57.55 7 2 82.34 7 3 43.13 7 4 88.02 7 5 28.75 7 6 89.12 #------------- Plane number 8 --------------- Atoms Defining Plane Distance esd C(331) ( 1) 0.0078 0.0047 C(332) ( 1) -0.0109 0.0056 C(333) ( 1) 0.0078 0.0072 C(334) ( 1) -0.0029 0.0076 C(335) ( 1) 0.0044 0.0075 C(336) ( 1) -0.0084 0.0060 Additional Atoms Distance C(33) ( 1) 0.0213 Cl(332 ( 1) -0.0774 Cl(336 ( 1) -0.0681 Mean deviation from plane is 0.0070 angstroms Chi-squared: 9.7 Dihedral angles between least-squares planes plane plane angle 8 1 80.76 8 2 164.55 8 3 78.79 8 4 155.02 8 5 85.20 8 6 159.65 8 7 82.32 #------------- Plane number 9 --------------- Atoms Defining Plane Distance esd O(341) ( 1) 0.0006 0.0043 O(342) ( 1) 0.0004 0.0037 C(34) ( 1) 0.0006 0.0049 C(341) ( 1) -0.0019 0.0050 Additional Atoms Distance C(33) ( 1) -0.0259 C(35) ( 1) 0.0271 C(343) ( 1) 0.0131 Mean deviation from plane is 0.0009 angstroms Chi-squared: 0.2 Dihedral angles between least-squares planes plane plane angle 9 1 56.01 9 2 82.49 9 3 41.59 9 4 87.61 9 5 27.24 9 6 88.82 9 7 1.54 9 8 82.13 #------------- Plane number 10 --------------- Atoms Defining Plane Distance esd O(41) ( 1) 0.0010 0.0037 N(42) ( 1) -0.0018 0.0044 C(43) ( 1) 0.0019 0.0049 C(44) ( 1) -0.0007 0.0046 C(45) ( 1) -0.0008 0.0053 Additional Atoms Distance C(431) ( 1) -0.0560 C(441) ( 1) 0.0338 Mean deviation from plane is 0.0013 angstroms Chi-squared: 0.4 Dihedral angles between least-squares planes plane plane angle 10 1 78.54 10 2 146.34 10 3 71.91 10 4 149.18 10 5 73.62 10 6 151.99 10 7 64.61 10 8 19.46 10 9 64.65 #------------- Plane number 11 --------------- Atoms Defining Plane Distance esd C(431) ( 1) -0.0072 0.0050 C(432) ( 1) -0.0016 0.0053 C(433) ( 1) 0.0124 0.0063 C(434) ( 1) -0.0086 0.0059 C(435) ( 1) -0.0031 0.0059 C(436) ( 1) 0.0079 0.0048 Additional Atoms Distance C(43) ( 1) -0.0475 Cl(432 ( 1) 0.0104 Cl(436 ( 1) 0.0728 Mean deviation from plane is 0.0068 angstroms Chi-squared: 11.0 Dihedral angles between least-squares planes plane plane angle 11 1 34.06 11 2 71.45 11 3 22.67 11 4 67.68 11 5 9.07 11 6 70.42 11 7 29.15 11 8 94.04 11 9 27.83 11 10 81.60 #------------- Plane number 12 --------------- Atoms Defining Plane Distance esd O(441) ( 1) -0.0030 0.0037 O(442) ( 1) -0.0018 0.0034 C(44) ( 1) -0.0030 0.0046 C(441) ( 1) 0.0110 0.0046 Additional Atoms Distance C(43) ( 1) 0.0049 C(45) ( 1) 0.0141 C(443) ( 1) 0.0851 Mean deviation from plane is 0.0047 angstroms Chi-squared: 7.0 Dihedral angles between least-squares planes plane plane angle 12 1 79.39 12 2 146.62 12 3 72.74 12 4 149.92 12 5 74.36 12 6 152.66 12 7 65.06 12 8 19.40 12 9 65.12 12 10 0.85 12 11 82.31 ; #------------------------------------------------------------------------------ #===END data_gjv4 _database_code_CSD 191572 #------------------------------------------------------------------------------ _audit_creation_date '2000-06-19' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; 2000-06-19 - Report on C11 H7 Cl2 N O3 by Anthony C. Willis for George J. Vuckovic and Christopher J. Easton 2000-06-20 - passes checkcif tests with 1 minor warning ; #------------------------------------------------------------------------------ _publ_requested_journal ' JCS Perkin 2 ' _publ_requested_category 'FO ' _publ_contact_author_name ' Anthony C. Willis ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' 61 2 6125 4109 ' _publ_contact_author_fax ' 61 2 6125 0750 ' _publ_contact_author_email ' willis@rsc.anu.edu.au ' loop_ _publ_author_name _publ_author_address ' Connie K. Y. Lee ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Christopher J. Easton ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Mariana Gebara-Coghlan ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Leo Radom ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Anthony P. Scott ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Gregory W. Simpson ' ; CSIRO Molecular Science, Bayview Ave, Clayton, Victoria 3168, Australia ; ' Anthony C. Willis ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_section_title ; Substituent effects in isoxazoles: identification of 4-substituted isoxazoles as Michael acceptors ; _publ_section_title_footnote ' ENTER ANY FOOTNOTES TO TITLE ' _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. 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. 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., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Blessing, R. H.; Acta Crystallogr., Section A, 51, 33-37 (1995). Blessing, R. H.; J. Appl. Crystallogr., 30, 421-426 (1997). ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 10.4382(3) _cell_length_b 10.2875(4) _cell_length_c 11.4036(5) _cell_angle_alpha 90 _cell_angle_beta 109.859(2) _cell_angle_gamma 90 _cell_volume 1151.73(7) _cell_formula_units_Z 4 _cell_measurement_temperature 200.0 _cell_measurement_reflns_used 17488 _cell_measurement_theta_min 4.076 _cell_measurement_theta_max 27.485 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y, -z' ' -x, -y, -z' '1/2+x,1/2-y, +z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 272.09 _chemical_formula_analytical ? _chemical_formula_sum 'C11 H7 Cl2 N O3 ' _chemical_formula_moiety 'C11 H7 Cl2 N O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 552.00 _exptl_absorpt_coefficient_mu 0.556 #units are mm-1 # Absorption correction _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min .751 _exptl_absorpt_correction_T_max .952 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) 0 0 1 0.0500 0 0 -1 0.0400 0 1 -1 0.1000 0 -1 1 0.1200 1 1 0 0.1100 -10 -6 -1 0.0700 6 -7 3 0.1300 -17 -1 10 0.1500 ; #------------------------------------------------------------------------------ _diffrn_special_details ; CCD data collecting conditions- omega scans of 2 deg/frame at rate of 20 sec/deg, crystal-detector distance 30mm, multiple scan sets so over 95 percent of data collected with 3-fold redundancy or more. ; _diffrn_ambient_temperature 200. _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'CCD' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_detector_area_resol_mean ? _diffrn_measurement_method 'CCD' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 20168 _reflns_number_total 2631 _reflns_number_gt 1686 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.05765 _diffrn_reflns_av_sigmaI/netI 0.130 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.15 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 44 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 28 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Cl 0 8 0.132 0.159 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N 0 4 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 12 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ 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_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom Cl(32) 0.54747(5) 0.70610(6) 0.04673(5) 0.0476(2) 1.000 . Uani d ? Cl(36) 0.35184(6) 1.00480(6) 0.33636(6) 0.0528(2) 1.000 . Uani d ? O(1) 0.6046(1) 0.6507(1) 0.4396(1) 0.0433(4) 1.000 . Uani d ? O(51) 0.8285(2) 0.6530(1) 0.6593(1) 0.0483(5) 1.000 . Uani d ? O(52) 0.8998(1) 0.8336(1) 0.5881(1) 0.0433(4) 1.000 . Uani d ? N(2) 0.4988(2) 0.6827(2) 0.3297(2) 0.0446(6) 1.000 . Uani d ? C(3) 0.5327(2) 0.7950(2) 0.2945(2) 0.0328(6) 1.000 . Uani d ? C(4) 0.6596(2) 0.8395(2) 0.3774(2) 0.0359(6) 1.000 . Uani d ? C(5) 0.6980(2) 0.7468(2) 0.4645(2) 0.0338(6) 1.000 . Uani d ? C(31) 0.4421(2) 0.8612(2) 0.1818(2) 0.0327(6) 1.000 . Uani d ? C(32) 0.4413(2) 0.8297(2) 0.0627(2) 0.0358(6) 1.000 . Uani d ? C(33) 0.3608(2) 0.8956(2) -0.0422(2) 0.0425(7) 1.000 . Uani d ? C(34) 0.2799(2) 0.9957(2) -0.0292(2) 0.0464(7) 1.000 . Uani d ? C(35) 0.2775(2) 1.0305(2) 0.0872(2) 0.0435(7) 1.000 . Uani d ? C(36) 0.3576(2) 0.9629(2) 0.1909(2) 0.0370(6) 1.000 . Uani d ? C(51) 0.8151(2) 0.7358(2) 0.5816(2) 0.0371(6) 1.000 . Uani d ? C(53) 1.0137(3) 0.8466(3) 0.7032(3) 0.0506(8) 1.000 . Uani d ? H(1) 0.703(2) 0.915(2) 0.372(2) 0.043 1.000 . Uiso d ? H(2) 0.365(2) 0.873(2) -0.120(2) 0.051 1.000 . Uiso d ? H(3) 0.225(2) 1.045(2) -0.101(2) 0.056 1.000 . Uiso d ? H(4) 0.221(2) 1.100(2) 0.094(2) 0.052 1.000 . Uiso d ? H(5) 0.987(2) 0.876(2) 0.770(2) 0.061 1.000 . Uiso d ? H(6) 1.074(2) 0.912(2) 0.684(2) 0.061 1.000 . Uiso d ? H(7) 1.056(3) 0.767(2) 0.726(2) 0.061 1.000 . Uiso d ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl(32) 0.0460(3) 0.0503(4) 0.0476(4) 0.0041(3) 0.0175(3) -0.0106(3) Cl(36) 0.0650(4) 0.0461(4) 0.0583(4) 0.0099(3) 0.0351(3) -0.0019(3) O(1) 0.0456(9) 0.0365(8) 0.0445(9) -0.0028(7) 0.0109(8) 0.0082(7) O(51) 0.056(1) 0.0429(9) 0.043(1) 0.0034(7) 0.0131(8) 0.0110(8) O(52) 0.0411(8) 0.0439(9) 0.0410(9) -0.0030(7) 0.0089(7) 0.0022(7) N(2) 0.041(1) 0.042(1) 0.046(1) -0.0043(9) 0.0090(9) 0.0058(9) C(3) 0.037(1) 0.028(1) 0.037(1) 0.0011(9) 0.017(1) -0.0021(9) C(4) 0.039(1) 0.030(1) 0.038(1) -0.0015(9) 0.013(1) 0.000(1) C(5) 0.037(1) 0.030(1) 0.038(1) 0.0017(9) 0.017(1) -0.0020(9) C(31) 0.030(1) 0.030(1) 0.038(1) -0.0045(8) 0.0118(9) -0.0009(9) C(32) 0.032(1) 0.035(1) 0.040(1) -0.0054(9) 0.012(1) -0.004(1) C(33) 0.039(1) 0.046(1) 0.039(1) -0.009(1) 0.008(1) -0.003(1) C(34) 0.037(1) 0.045(1) 0.048(2) -0.006(1) 0.002(1) 0.007(1) C(35) 0.034(1) 0.034(1) 0.059(2) 0.0017(9) 0.011(1) 0.004(1) C(36) 0.035(1) 0.032(1) 0.045(1) -0.0030(9) 0.016(1) -0.001(1) C(51) 0.039(1) 0.036(1) 0.040(1) 0.006(1) 0.018(1) -0.004(1) C(53) 0.045(1) 0.053(2) 0.047(2) 0.000(1) 0.006(1) -0.002(1) #------------------------------------------------------------------------------ _refine_special_details ; \s^2^(Fo) is the larger of the value from averaging of equivalent reflections or counting statistics. All hydrogen atoms were observed in difference map and refined positionally. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1/[\s^2^(Fo)] ; _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1686 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_all 0.0436 _refine_ls_wR_factor_ref 0.0376 _refine_ls_goodness_of_fit_all 0.845 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_shift/su_max 0.0120 _refine_ls_shift/su_mean 0.0020 _refine_diff_density_min -0.24 _refine_diff_density_max 0.22 #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl(32) C(32) 1.737(2) . . yes Cl(36) C(36) 1.735(2) . . yes O(1) N(2) 1.400(2) . . yes O(1) C(5) 1.349(2) . . yes O(51) C(51) 1.203(2) . . yes O(52) C(51) 1.325(2) . . yes O(52) C(53) 1.447(3) . . yes N(2) C(3) 1.310(2) . . yes C(3) C(4) 1.417(3) . . yes C(3) C(31) 1.478(3) . . yes C(4) C(5) 1.337(3) . . yes C(4) H(1) 0.91(2) . . no C(5) C(51) 1.477(3) . . yes C(31) C(32) 1.393(3) . . yes C(31) C(36) 1.395(3) . . yes C(32) C(33) 1.383(3) . . yes C(33) C(34) 1.372(3) . . yes C(33) H(2) 0.94(2) . . no C(34) C(35) 1.384(3) . . yes C(34) H(3) 0.97(2) . . no C(35) C(36) 1.382(3) . . yes C(35) H(4) 0.95(2) . . no C(53) H(5) 0.94(2) . . no C(53) H(6) 0.99(2) . . no C(53) H(7) 0.92(2) . . no #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N(2) O(1) C(5) 108.0(1) . . . yes C(51) O(52) C(53) 116.7(2) . . . yes O(1) N(2) C(3) 105.6(2) . . . yes N(2) C(3) C(4) 111.7(2) . . . yes N(2) C(3) C(31) 120.8(2) . . . yes C(4) C(3) C(31) 127.5(2) . . . yes C(3) C(4) C(5) 103.9(2) . . . yes C(3) C(4) H(1) 127(1) . . . no C(5) C(4) H(1) 129(1) . . . no O(1) C(5) C(4) 110.7(2) . . . yes O(1) C(5) C(51) 116.8(2) . . . yes C(4) C(5) C(51) 132.3(2) . . . yes C(3) C(31) C(32) 122.0(2) . . . yes C(3) C(31) C(36) 121.0(2) . . . yes C(32) C(31) C(36) 116.9(2) . . . yes Cl(32) C(32) C(31) 118.7(2) . . . yes Cl(32) C(32) C(33) 119.3(2) . . . yes C(31) C(32) C(33) 122.0(2) . . . yes C(32) C(33) C(34) 119.3(2) . . . yes C(32) C(33) H(2) 120(1) . . . no C(34) C(33) H(2) 121(1) . . . no C(33) C(34) C(35) 120.7(2) . . . yes C(33) C(34) H(3) 121(1) . . . no C(35) C(34) H(3) 118(1) . . . no C(34) C(35) C(36) 119.2(2) . . . yes C(34) C(35) H(4) 119(1) . . . no C(36) C(35) H(4) 122(1) . . . no Cl(36) C(36) C(31) 119.1(2) . . . yes Cl(36) C(36) C(35) 119.0(2) . . . yes C(31) C(36) C(35) 121.9(2) . . . yes O(51) C(51) O(52) 126.0(2) . . . yes O(51) C(51) C(5) 125.1(2) . . . yes O(52) C(51) C(5) 108.9(2) . . . yes O(52) C(53) H(5) 112(2) . . . no O(52) C(53) H(6) 105(1) . . . no O(52) C(53) H(7) 110(2) . . . no H(5) C(53) H(6) 110(2) . . . no H(5) C(53) H(7) 108(2) . . . no H(6) C(53) H(7) 112(2) . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl(32) C(35) 3.339(2) . 4_565 no Cl(32) C(34) 3.518(2) . 4_565 no Cl(32) C(36) 3.548(2) . 4_565 no Cl(32) C(34) 3.597(2) . 3_675 no Cl(36) O(52) 3.455(2) . 3_676 no Cl(36) C(51) 3.484(2) . 3_676 no Cl(36) O(1) 3.560(2) . 4_465 no Cl(36) C(5) 3.572(2) . 3_676 no O(1) O(52) 3.150(2) . 4_465 no O(1) O(52) 3.276(2) . 2_646 no O(1) C(53) 3.444(3) . 4_465 no O(1) C(53) 3.549(3) . 2_646 no O(51) C(4) 3.260(3) . 2_646 no O(51) C(33) 3.342(3) . 4_566 no O(51) C(53) 3.487(3) . 4_465 no O(52) N(2) 3.443(2) . 4_565 no N(2) C(53) 3.476(4) . 2_646 no C(32) C(34) 3.549(3) . 3_675 no C(32) C(33) 3.556(3) . 3_675 no C(33) C(33) 3.477(4) . 3_675 no #------------------------------------------------------------------------------ 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 Cl(32) C(32) C(31) C(3) . . . . 1.6(3) no Cl(32) C(32) C(31) C(36) . . . . 178.6(1) no Cl(32) C(32) C(33) C(34) . . . . -178.1(2) no Cl(36) C(36) C(31) C(3) . . . . -4.0(3) no Cl(36) C(36) C(31) C(32) . . . . 178.9(1) no Cl(36) C(36) C(35) C(34) . . . . -178.8(2) no O(1) N(2) C(3) C(4) . . . . 0.5(2) no O(1) N(2) C(3) C(31) . . . . -178.5(2) no O(1) C(5) C(4) C(3) . . . . 0.3(2) no O(1) C(5) C(51) O(51) . . . . -5.1(3) no O(1) C(5) C(51) O(52) . . . . 176.7(2) no O(51) C(51) O(52) C(53) . . . . -4.5(3) no O(51) C(51) C(5) C(4) . . . . 170.4(2) no O(52) C(51) C(5) C(4) . . . . -7.7(3) no N(2) O(1) C(5) C(4) . . . . 0.0(2) no N(2) O(1) C(5) C(51) . . . . 176.5(2) no N(2) C(3) C(4) C(5) . . . . -0.5(2) no N(2) C(3) C(31) C(32) . . . . -82.8(2) no N(2) C(3) C(31) C(36) . . . . 100.3(2) no C(3) N(2) O(1) C(5) . . . . -0.3(2) no C(3) C(4) C(5) C(51) . . . . -175.5(2) no C(3) C(31) C(32) C(33) . . . . -177.1(2) no C(3) C(31) C(36) C(35) . . . . 176.5(2) no C(4) C(3) C(31) C(32) . . . . 98.3(3) no C(4) C(3) C(31) C(36) . . . . -78.6(3) no C(5) C(4) C(3) C(31) . . . . 178.5(2) no C(5) C(51) O(52) C(53) . . . . 173.7(2) no C(31) C(32) C(33) C(34) . . . . 0.6(3) no C(31) C(36) C(35) C(34) . . . . 0.6(3) no C(32) C(31) C(36) C(35) . . . . -0.6(3) no C(32) C(33) C(34) C(35) . . . . -0.5(3) no C(33) C(32) C(31) C(36) . . . . 0.0(3) no C(33) C(34) C(35) C(36) . . . . -0.1(3) no #------------------------------------------------------------------------------ _geom_special_details ; Table of Least-Squares Planes #----------------------------- #------------- Plane number 1 --------------- Atoms Defining Plane Distance esd O(1) ( 1) -0.0007 0.0015 N(2) ( 1) 0.0022 0.0019 C(3) ( 1) -0.0026 0.0018 C(4) ( 1) 0.0025 0.0021 C(5) ( 1) -0.0005 0.0018 Additional Atoms Distance C(31) ( 1) -0.0335 C(51) ( 1) -0.0841 H(1) ( 1) -0.0001 Mean deviation from plane is 0.0017 angstroms Chi-squared: 5.0 #------------- Plane number 2 --------------- Atoms Defining Plane Distance esd C(31) ( 1) 0.0015 0.0018 C(32) ( 1) 0.0017 0.0019 C(33) ( 1) -0.0041 0.0021 C(34) ( 1) 0.0016 0.0021 C(35) ( 1) 0.0025 0.0021 C(36) ( 1) -0.0039 0.0019 Additional Atoms Distance Cl(32) ( 1) 0.0453 Cl(36) ( 1) -0.0340 C(3) ( 1) 0.0711 H(2) ( 1) 0.0248 H(3) ( 1) 0.0265 H(4) ( 1) 0.0076 Mean deviation from plane is 0.0025 angstroms Chi-squared: 11.5 Dihedral angles between least-squares planes plane plane angle 2 1 80.59 #------------- Plane number 3 --------------- Atoms Defining Plane Distance esd O(51) ( 1) -0.0025 0.0015 O(52) ( 1) -0.0019 0.0014 C(5) ( 1) -0.0029 0.0018 C(51) ( 1) 0.0105 0.0019 Additional Atoms Distance C(53) ( 1) -0.1346 O(1) ( 1) 0.0759 N(2) ( 1) -0.0328 C(3) ( 1) -0.1759 C(4) ( 1) -0.1561 Mean deviation from plane is 0.0044 angstroms Chi-squared: 37.9 Dihedral angles between least-squares planes plane plane angle 3 1 6.79 3 2 84.01 ; #------------------------------------------------------------------------------ #===END data_ckl3 _database_code_CSD 191573 #------------------------------------------------------------------------------ _audit_creation_date '2000-06-29' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; 2000-06-30 - Report on C6 H7 N O3 by Anthony C. Willis for Connie K. Y. Lee and Christopher J. Easton 2000-06-30 - passes checkcif tests with 1 minor warning ; #------------------------------------------------------------------------------ _publ_requested_journal ' JCS Perkin 2 ' _publ_requested_category 'FO ' _publ_contact_author_name ' Anthony C. Willis ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' 61 2 6125 4109 ' _publ_contact_author_fax ' 61 2 6125 0750 ' _publ_contact_author_email ' willis@rsc.anu.edu.au ' loop_ _publ_author_name _publ_author_address ' Connie K. Y. Lee ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Christopher J. Easton ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Mariana Gebara-Coghlan ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Leo Radom ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Anthony P. Scott ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Gregory W. Simpson ' ; CSIRO Molecular Science, Bayview Ave, Clayton, Victoria 3168, Australia ; ' Anthony C. Willis ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_section_title ; Substituent effects in isoxazoles: identification of 4-substituted isoxazoles as Michael acceptors ; _publ_section_title_footnote ' ENTER ANY FOOTNOTES TO TITLE ' _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. 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. 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., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Blessing, R. H.; Acta Crystallogr., Section A, 51, 33-37 (1995). Blessing, R. H.; J. Appl. Crystallogr., 30, 421-426 (1997). ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 7.8027(3) _cell_length_b 11.2422(5) _cell_length_c 8.4806(4) _cell_angle_alpha 90 _cell_angle_beta 111.428(2) _cell_angle_gamma 90 _cell_volume 692.49(5) _cell_formula_units_Z 4 _cell_measurement_temperature 200.0 _cell_measurement_reflns_used 9111 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 27.48 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 141.13 _chemical_formula_analytical ? _chemical_formula_sum 'C6 H7 N O3 ' _chemical_formula_moiety 'C6 H7 N O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 296.00 _exptl_absorpt_coefficient_mu 0.110 #units are mm-1 # Absorption correction _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min .888 _exptl_absorpt_correction_T_max .994 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) 1 0 0 0.0200 -1 0 0 0.1000 1 -1 0 0.0100 0 1 0 0.1500 0 -1 0 0.1400 0 -1 1 0.0800 0 1 -1 0.1200 0 1 2 0.1200 0 -1 -2 0.1600 ; #------------------------------------------------------------------------------ _diffrn_special_details ; CCD data collecting conditions- omega scans of 2 deg/frame at rate of 20 sec/deg, crystal-detector distance 30mm, multiple scan sets so over 94 percent of data collected with 4-fold redundancy or more. ; _diffrn_ambient_temperature 200.0 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'CCD' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_detector_area_resol_mean ? _diffrn_measurement_method 'CCD' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 14023 _reflns_number_total 1573 _reflns_number_gt 904 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.05880 _diffrn_reflns_av_sigmaI/netI 0.140 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.45 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 24 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 28 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 4 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 12 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ 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_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.8648(2) 0.1281(1) 0.5621(2) 0.0494(4) 1.000 . Uani d ? O(2) 0.4879(2) -0.1816(1) 0.3079(2) 0.0541(4) 1.000 . Uani d ? O(3) 0.4321(2) -0.0083(1) 0.1671(1) 0.0496(4) 1.000 . Uani d ? N(1) 0.9201(2) 0.0232(1) 0.6625(2) 0.0490(5) 1.000 . Uani d ? C(1) 0.8053(2) -0.0596(2) 0.5783(2) 0.0407(5) 1.000 . Uani d ? C(2) 0.6744(2) -0.0143(1) 0.4248(2) 0.0339(5) 1.000 . Uani d ? C(3) 0.7203(3) 0.1010(2) 0.4239(2) 0.0416(5) 1.000 . Uani d ? C(4) 0.8238(4) -0.1823(2) 0.6479(3) 0.0631(7) 1.000 . Uani d ? C(5) 0.5243(2) -0.0779(2) 0.2973(2) 0.0385(5) 1.000 . Uani d ? C(6) 0.2800(3) -0.0635(3) 0.0316(3) 0.0626(7) 1.000 . Uani d ? H(1) 0.663(3) 0.167(2) 0.341(2) 0.065(6) 1.000 . Uiso d ? H(2) 0.931(3) -0.190(2) 0.744(3) 0.101(5) 1.000 . Uiso d ? H(3) 0.712(3) -0.206(2) 0.667(3) 0.101 1.000 . Uiso d ? H(4) 0.835(3) -0.242(2) 0.570(3) 0.101 1.000 . Uiso d ? H(5) 0.327(3) -0.129(2) -0.023(3) 0.089(4) 1.000 . Uiso d ? H(6) 0.196(3) -0.092(2) 0.077(3) 0.089 1.000 . Uiso d ? H(7) 0.218(3) 0.004(2) -0.058(3) 0.089 1.000 . Uiso d ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0452(8) 0.0485(8) 0.0453(8) -0.0063(6) 0.0054(7) -0.0036(6) O(2) 0.0623(9) 0.0397(8) 0.0523(9) -0.0083(7) 0.0112(7) -0.0075(6) O(3) 0.0444(8) 0.0553(8) 0.0366(8) -0.0047(7) -0.0001(6) 0.0012(6) N(1) 0.0401(9) 0.060(1) 0.0398(9) 0.0000(8) 0.0056(8) 0.0035(8) C(1) 0.036(1) 0.046(1) 0.038(1) 0.0039(9) 0.0117(9) 0.0035(9) C(2) 0.0322(9) 0.036(1) 0.032(1) 0.0028(8) 0.0091(8) -0.0005(8) C(3) 0.037(1) 0.044(1) 0.037(1) 0.0003(9) 0.0058(9) -0.0017(9) C(4) 0.061(1) 0.055(1) 0.064(2) 0.010(1) 0.012(1) 0.024(1) C(5) 0.038(1) 0.042(1) 0.034(1) 0.0029(9) 0.0115(9) -0.0035(8) C(6) 0.050(1) 0.085(2) 0.038(1) -0.014(1) -0.001(1) -0.008(1) #------------------------------------------------------------------------------ _refine_special_details ; \s^2^(Fo) is the larger of the value from averaging of equivalent reflections or counting statistics. All hydrogen atoms were observed in difference map and refined with isotropic displacement parameters. B constrained to be equal for H atoms of each methyl group. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1/[\s^2^(Fo)] ; _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 904 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_number_constraints 4 _refine_ls_R_factor_all 0.0705 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_all 0.0475 _refine_ls_wR_factor_ref 0.0402 _refine_ls_goodness_of_fit_all 0.876 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_shift/su_max 0.0030 _refine_ls_shift/su_mean 0.0004 _refine_diff_density_min -0.16 _refine_diff_density_max 0.12 #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) N(1) 1.427(2) . . yes O(1) C(3) 1.331(2) . . yes O(2) C(5) 1.211(2) . . yes O(3) C(5) 1.330(2) . . yes O(3) C(6) 1.455(2) . . yes N(1) C(1) 1.308(2) . . yes C(1) C(2) 1.423(2) . . yes C(1) C(4) 1.487(3) . . yes C(2) C(3) 1.345(2) . . yes C(2) C(5) 1.459(2) . . yes C(3) H(1) 1.01(2) . . no C(4) H(2) 0.93(3) . . no C(4) H(3) 0.98(3) . . no C(4) H(4) 0.97(3) . . no C(6) H(5) 1.01(2) . . no C(6) H(6) 0.93(3) . . no C(6) H(7) 1.06(3) . . no #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N(1) O(1) C(3) 108.1(1) . . . yes C(5) O(3) C(6) 116.2(2) . . . yes O(1) N(1) C(1) 105.3(1) . . . yes N(1) C(1) C(2) 111.4(2) . . . yes N(1) C(1) C(4) 119.7(2) . . . yes C(2) C(1) C(4) 128.9(2) . . . yes C(1) C(2) C(3) 104.3(2) . . . yes C(1) C(2) C(5) 128.0(2) . . . yes C(3) C(2) C(5) 127.7(2) . . . yes O(1) C(3) C(2) 111.0(2) . . . yes O(1) C(3) H(1) 117(1) . . . no C(2) C(3) H(1) 132(1) . . . no C(1) C(4) H(2) 111(2) . . . no C(1) C(4) H(3) 111(1) . . . no C(1) C(4) H(4) 113(2) . . . no H(2) C(4) H(3) 114(2) . . . no H(2) C(4) H(4) 105(2) . . . no H(3) C(4) H(4) 103(2) . . . no O(2) C(5) O(3) 123.9(2) . . . yes O(2) C(5) C(2) 124.3(2) . . . yes O(3) C(5) C(2) 111.8(2) . . . yes O(3) C(6) H(5) 110(1) . . . no O(3) C(6) H(6) 109(2) . . . no O(3) C(6) H(7) 107(1) . . . no H(5) C(6) H(6) 111(2) . . . no H(5) C(6) H(7) 110(2) . . . no H(6) C(6) H(7) 110(2) . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) C(1) 3.299(2) . 3_756 no O(1) O(2) 3.372(2) . 3_656 no O(1) N(1) 3.417(2) . 3_756 no O(1) C(4) 3.482(2) . 2_756 no O(1) C(4) 3.551(3) . 3_756 no O(2) C(3) 3.185(2) . 2_645 no O(2) C(3) 3.366(2) . 3_656 no O(3) C(6) 3.362(3) . 3_655 no O(3) O(3) 3.375(2) . 3_655 no O(3) C(1) 3.405(2) . 3_656 no O(3) N(1) 3.545(2) . 3_656 no N(1) C(3) 3.444(2) . 3_756 no N(1) N(1) 3.454(3) . 3_756 no N(1) C(1) 3.482(2) . 3_756 no N(1) C(6) 3.494(3) . 1_656 no N(1) C(2) 3.504(2) . 3_756 no N(1) C(6) 3.512(3) . 3_656 no C(1) C(5) 3.478(2) . 3_656 no C(2) C(2) 3.418(3) . 3_656 no C(2) C(5) 3.421(2) . 3_656 no C(3) C(5) 3.549(3) . 3_656 no #------------------------------------------------------------------------------ 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) N(1) C(1) C(2) . . . . 0.0(2) no O(1) N(1) C(1) C(4) . . . . 180.0(2) no O(1) C(3) C(2) C(1) . . . . -0.2(2) no O(1) C(3) C(2) C(5) . . . . 179.6(2) no O(2) C(5) O(3) C(6) . . . . -0.3(3) no O(2) C(5) C(2) C(1) . . . . 1.6(3) no O(2) C(5) C(2) C(3) . . . . -178.2(2) no O(3) C(5) C(2) C(1) . . . . -178.2(2) no O(3) C(5) C(2) C(3) . . . . 2.0(2) no N(1) O(1) C(3) C(2) . . . . 0.2(2) no N(1) C(1) C(2) C(3) . . . . 0.1(2) no N(1) C(1) C(2) C(5) . . . . -179.7(2) no C(1) N(1) O(1) C(3) . . . . -0.1(2) no C(2) C(5) O(3) C(6) . . . . 179.4(2) no C(3) C(2) C(1) C(4) . . . . -179.8(2) no C(4) C(1) C(2) C(5) . . . . 0.4(3) no #------------------------------------------------------------------------------ _geom_special_details ; Table of Least-Squares Planes #----------------------------- #------------- Plane number 1 --------------- Atoms Defining Plane Distance esd O(1) ( 1) -0.0006 0.0013 N(1) ( 1) 0.0003 0.0015 C(1) ( 1) 0.0002 0.0017 C(2) ( 1) -0.0008 0.0015 C(3) ( 1) 0.0016 0.0019 Additional Atoms Distance O(2) ( 1) -0.0405 O(3) ( 1) 0.0324 C(4) ( 1) 0.0021 C(5) ( 1) -0.0075 C(6) ( 1) 0.0426 Mean deviation from plane is 0.0007 angstroms Chi-squared: 1.2 #------------- Plane number 2 --------------- Atoms Defining Plane Distance esd O(2) ( 1) 0.0003 0.0013 O(3) ( 1) 0.0002 0.0012 C(2) ( 1) 0.0003 0.0015 C(5) ( 1) -0.0014 0.0017 Additional Atoms Distance O(1) ( 1) -0.0287 N(1) ( 1) 0.0183 C(1) ( 1) 0.0346 C(3) ( 1) -0.0345 C(4) ( 1) 0.0846 C(6) ( 1) 0.0117 Mean deviation from plane is 0.0006 angstroms Chi-squared: 0.8 Dihedral angles between least-squares planes plane plane angle 2 1 1.87 ; #------------------------------------------------------------------------------ #===END data_ckl1 _database_code_CSD 191574 #------------------------------------------------------------------------------ _audit_creation_date '2000-01-18' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; ? ; #------------------------------------------------------------------------------ _publ_requested_journal ' JCS Perkin 2 ' _publ_requested_category ' FO' _publ_contact_author_name ' Anthony C. Willis ' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' 61 2 6125 4109 ' _publ_contact_author_fax ' 61 2 6125 0750 ' _publ_contact_author_email ' willis@rsc.anu.edu.au ' loop_ _publ_author_name _publ_author_address ' Connie K. Y. Lee ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Christopher J. Easton ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Mariana Gebara-Coghlan ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Leo Radom ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Anthony P. Scott ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; ' Gregory W. Simpson ' ; CSIRO Molecular Science, Bayview Ave, Clayton, Victoria 3168, Australia ; ' Anthony C. Willis ' ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_section_title ; Substituent effects in isoxazoles: identification of 4-substituted isoxazoles as Michael acceptors ; _publ_section_title_footnote ' ENTER ANY FOOTNOTES TO TITLE ' _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. 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. 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., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ _computing_cell_refinement 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 5.8086(2) _cell_length_b 6.3238(3) _cell_length_c 8.8391(4) _cell_angle_alpha 90 _cell_angle_beta 92.435(2) _cell_angle_gamma 90 _cell_volume 324.39(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200.0 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/m ' _symmetry_Int_Tables_number 11 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y, -z' ' -x, -y, -z' ' +x,1/2-y, +z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 141.13 _chemical_formula_analytical ? _chemical_formula_sum 'C6 H7 N O3 ' _chemical_formula_moiety 'C6 H7 N O3 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 148.00 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_special_details ; Absorption corrected in Scalepack processing ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 200.0 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'CCD' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_detector_area_resol_mean ? _diffrn_measurement_method ' \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 9358 _reflns_number_total 749 _reflns_number_gt 693 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_sigmaI/netI 0.030 _diffrn_reflns_theta_full 26.7 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 26.74 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 12 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 14 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 2 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 6 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ 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_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.4487(2) 0.2500 0.4885(1) 0.0315(3) 1.0 ST Uani d ? O(2) 0.7107(2) 0.2500 0.8564(1) 0.0453(4) 1.0 ST Uani d ? O(3) 0.3395(2) 0.2500 0.7759(1) 0.0323(3) 1.0 ST Uani d ? N(1) 0.5495(2) 0.2500 0.3455(1) 0.0340(4) 1.0 ST Uani d ? C(1) 0.7726(2) 0.2500 0.3728(2) 0.0288(4) 1.0 ST Uani d ? C(2) 0.8283(2) 0.2500 0.5308(2) 0.0288(4) 1.0 ST Uani d ? C(3) 0.6221(2) 0.2500 0.5950(2) 0.0274(4) 1.0 ST Uani d ? C(4) 0.9321(3) 0.2500 0.2459(2) 0.0382(5) 1.0 ST Uani d ? C(5) 0.5639(2) 0.2500 0.7563(2) 0.0291(4) 1.0 ST Uani d ? C(6) 0.2730(3) 0.2500 0.9333(2) 0.0388(5) 1.0 ST Uani d ? H(1) 0.985(3) 0.2500 0.583(2) 0.045(5) 1.0 S Uiso d ? H(2) 0.859(4) 0.2500 0.152(3) 0.057(3) 1.0 S Uiso d ? H(3) 1.033(3) 0.124(2) 0.250(2) 0.057 1.000 . Uiso d ? H(4) 0.115(4) 0.2500 0.930(3) 0.058(3) 1.0 S Uiso d ? H(5) 0.330(2) 0.126(2) 0.984(2) 0.058 1.000 . Uiso d ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0251(6) 0.0408(6) 0.0285(6) 0.0000 0.0011(4) 0.0000 O(2) 0.0292(6) 0.0756(9) 0.0307(6) 0.0000 -0.0019(5) 0.0000 O(3) 0.0247(6) 0.0424(6) 0.0300(6) 0.0000 0.0035(4) 0.0000 N(1) 0.0337(7) 0.0409(7) 0.0275(7) 0.0000 0.0027(5) 0.0000 C(1) 0.0305(8) 0.0264(7) 0.0294(8) 0.0000 0.0029(6) 0.0000 C(2) 0.0250(8) 0.0306(7) 0.0306(8) 0.0000 0.0000(6) 0.0000 C(3) 0.0268(7) 0.0265(7) 0.0286(8) 0.0000 -0.0014(5) 0.0000 C(4) 0.0366(9) 0.0459(9) 0.0326(9) 0.0000 0.0071(7) 0.0000 C(5) 0.0268(7) 0.0312(8) 0.0296(8) 0.0000 0.0024(6) 0.0000 C(6) 0.0316(9) 0.054(1) 0.0310(9) 0.0000 0.0086(7) 0.0000 #------------------------------------------------------------------------------ _refine_special_details ; Hydrogen atoms refined positionally and isotropic displacement factors, with restraints U(H3)=U(H2) and U(H5)=U(H4). ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00040|Fo|^2^]' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 693 _refine_ls_number_parameters 76 _refine_ls_number_restraints 0 _refine_ls_number_constraints 2 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_all 0.0539 _refine_ls_wR_factor_ref 0.0526 _refine_ls_goodness_of_fit_all 2.078 _refine_ls_goodness_of_fit_ref 2.117 _refine_ls_shift/su_max 0.0053 _refine_ls_shift/su_mean 0.0014 _refine_diff_density_min -0.17 _refine_diff_density_max 0.25 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) N(1) 1.416(2) . . yes O(1) C(3) 1.349(2) . . yes O(2) C(5) 1.203(2) . . yes O(3) C(5) 1.322(2) . . yes O(3) C(6) 1.460(2) . . yes N(1) C(1) 1.308(2) . . yes C(1) C(2) 1.420(2) . . yes C(1) C(4) 1.485(2) . . yes C(2) C(3) 1.347(2) . . yes C(2) H(1) 1.00(2) . . no C(3) C(5) 1.479(2) . . yes C(4) H(2) 0.92(2) . . no C(4) H(3) 0.99(1) . . no C(4) H(3) 0.99(1) . 4 no C(6) H(4) 0.92(2) . . no C(6) H(5) 0.96(2) . . no C(6) H(5) 0.96(2) . 4 no #------------------------------------------------------------------------------ loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N(1) O(1) C(3) 107.4(1) . . . yes C(5) O(3) C(6) 115.3(1) . . . yes O(1) N(1) C(1) 106.2(1) . . . yes N(1) C(1) C(2) 111.4(1) . . . yes N(1) C(1) C(4) 120.4(1) . . . yes C(2) C(1) C(4) 128.3(1) . . . yes C(1) C(2) C(3) 104.2(1) . . . yes C(1) C(2) H(1) 128(1) . . . no C(3) C(2) H(1) 128(1) . . . no O(1) C(3) C(2) 110.9(1) . . . yes O(1) C(3) C(5) 118.6(1) . . . yes C(2) C(3) C(5) 130.5(1) . . . yes C(1) C(4) H(2) 114(1) . . . no C(1) C(4) H(3) 111.1(7) . . . no C(1) C(4) H(3) 111.1(7) . . 4 no H(2) C(4) H(3) 106(1) . . . no H(2) C(4) H(3) 106(1) . . 4 no H(3) C(4) H(3) 108(2) . . 4 no O(2) C(5) O(3) 125.2(1) . . . yes O(2) C(5) C(3) 121.7(1) . . . yes O(3) C(5) C(3) 113.2(1) . . . yes O(3) C(6) H(4) 106(1) . . . no O(3) C(6) H(5) 110.3(8) . . . no O(3) C(6) H(5) 110.3(8) . . 4 no H(4) C(6) H(5) 110(1) . . . no H(4) C(6) H(5) 110(1) . . 4 no H(5) C(6) H(5) 110(2) . . 4 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) O(1) 3.2223(4) . 2_656 no O(1) O(1) 3.2223(4) . 2_646 no O(1) C(3) 3.2690(4) . 2_656 no O(1) C(3) 3.2690(4) . 2_646 no O(1) N(1) 3.4856(6) . 2_656 no O(1) N(1) 3.4856(6) . 2_646 no O(1) C(2) 3.5486(8) . 2_656 no O(1) C(2) 3.5486(8) . 2_646 no O(2) C(6) 3.308(2) . 1_655 no O(3) N(1) 3.4093(6) . 2_656 no O(3) N(1) 3.4093(6) . 2_646 no O(3) C(1) 3.4753(7) . 2_656 no O(3) C(1) 3.4753(7) . 2_646 no O(3) C(4) 3.5353(9) . 2_656 no O(3) C(4) 3.5353(9) . 2_646 no N(1) C(5) 3.3453(6) . 2_656 no N(1) C(5) 3.3453(6) . 2_646 no N(1) C(3) 3.3634(6) . 2_656 no N(1) C(3) 3.3634(6) . 2_646 no C(4) C(6) 3.467(2) . 1_654 no #------------------------------------------------------------------------------ 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) N(1) C(1) C(2) . . . . 0.0000(3) no O(1) N(1) C(1) C(4) . . . . 180.0000 no O(1) C(3) C(2) C(1) . . . . 0.0000 no O(1) C(3) C(5) O(2) . . . . 180.0000(1) no O(1) C(3) C(5) O(3) . . . . 0.0000 no O(2) C(5) O(3) C(6) . . . . 0.0000 no O(2) C(5) C(3) C(2) . . . . 0.0000(1) no O(3) C(5) C(3) C(2) . . . . 180.0000(1) no N(1) O(1) C(3) C(2) . . . . 0.0000(2) no N(1) O(1) C(3) C(5) . . . . 180.0000(1) no N(1) C(1) C(2) C(3) . . . . 0.0000(1) no C(1) N(1) O(1) C(3) . . . . 0.0000(2) no C(1) C(2) C(3) C(5) . . . . 180.0000(2) no C(3) C(2) C(1) C(4) . . . . 180.0000(1) no C(3) C(5) O(3) C(6) . . . . 180.0000(1) no #------------------------------------------------------------------------------ #===END