data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address 'Steve Davies' ;Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA UK ; 'Caroline Aciro' ;Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA UK ; 'Tim Claridge ' ;Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA UK ; 'Paul M. Roberts ' ;Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA UK ; 'Angela J. Russell ' ;Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA UK ; 'James Thomson' '' _publ_contact_author_name 'Prof S Davies' _publ_contact_author_email STEVE.DAVIES@CHEM.OX.AC.UK _publ_section_title ; Ammonium directed dihydroxylation of 3-amino-cyclohex-1-enes: development of a metal-free dihydroxylation protocol ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? loop_ _publ_author_footnote ; ? # Footnote for author 1 ; ; ? # Footnote 2 ; _publ_contact_author_address ;Department of Chemistry Chemistry Research Laboratory University of Oxford Mansfield Road Oxford OX1 3TA UK ; _publ_contact_author_fax '+44 1865 275633' _publ_contact_author_phone '+44 1865 275695' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Org.Biomol.Chem. The figures will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Dr Angela Russell' # Attachment 'CCDC679350' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 679350' _audit_creation_date 08-01-31 _audit_creation_method CRYSTALS_ver_12.84 #_oxford_structure_analysis_title '1310821 SGD195' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 24.5125(2) _cell_length_b 9.82110(10) _cell_length_c 30.9595(4) _cell_angle_alpha 90 _cell_angle_beta 106.7096(5) _cell_angle_gamma 90 _cell_volume 7138.47(13) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 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 C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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 C 4.2.6.8 and 6.1.1.4' 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 C 4.2.6.8 and 6.1.1.4' 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 C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 12 # Given Formula = C22 H26 Cl3 N1 O4 # Dc = 1.33 Fooo = 3340.00 Mu = 4.12 M = 712.22 # Found Formula = C17.50 H18 Cl6.67 N0.67 O4.67 # Dc = 1.53 FOOO = 3340.00 Mu = 8.23 M = 823.03 _chemical_formula_sum 'C17.50 H18 Cl6.67 N0.67 O4.67' _chemical_formula_moiety 'C17.50 H18 Cl6.67 N0.67 O4.67' _chemical_compound_source ? _chemical_formula_weight 548.69 _cell_measurement_reflns_used 8099 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 3340 _exptl_absorpt_coefficient_mu 0.823 # Sheldrick geometric approximatio 0.85 0.85 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.85 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 14748 _reflns_number_total 7984 _diffrn_reflns_av_R_equivalents 0.034 # Number of reflections with Friedels Law is 7984 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 8166 _diffrn_reflns_theta_min 5.138 _diffrn_reflns_theta_max 27.466 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.917 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _reflns_limit_h_min -31 _reflns_limit_h_max 30 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 40 #_oxford_diffrn_Wilson_B_factor 3.56 #_oxford_diffrn_Wilson_scale 23.55 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.53 _refine_diff_density_max 2.00 _refine_ls_number_reflns 5826 _refine_ls_number_restraints 0 _refine_ls_number_parameters 402 #_refine_ls_R_factor_ref 0.0918 _refine_ls_wR_factor_ref 0.0951 _refine_ls_goodness_of_fit_ref 1.0849 #_reflns_number_all 7984 _refine_ls_R_factor_all 0.1129 _refine_ls_wR_factor_all 0.1107 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 5826 _refine_ls_R_factor_gt 0.0918 _refine_ls_wR_factor_gt 0.0951 _refine_ls_shift/su_max 0.003363 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed # WARNING. The IUCr will not accept Unit Weights _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Quasi-Unit weights W = 1.0 or 1./2F ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. 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 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.4895(2) -0.1750(7) 0.94748(18) 0.0424 1.0000 Uani . . . . . . Cl2 Cl 0.44306(7) -0.2354(2) 0.97711(6) 0.0671 1.0000 Uani . . . . . . C3 C 0.5528(2) -0.1793(5) 0.97640(17) 0.0322 1.0000 Uani . . . . . . O4 O 0.58655(15) -0.1100(4) 0.96126(11) 0.0367 1.0000 Uani . . . . . . O5 O 0.56513(15) -0.2514(4) 1.01023(12) 0.0356 1.0000 Uani . . . . . . Cl6 Cl 0.46949(6) -0.00493(17) 0.93059(5) 0.0517 1.0000 Uani . . . . . . Cl7 Cl 0.48342(7) -0.27780(18) 0.89910(5) 0.0557 1.0000 Uani . . . . . . C8 C 0.3356(3) -0.1472(6) 0.80758(19) 0.0464 1.0000 Uani . . . . . . C9 C 0.3215(2) -0.1719(6) 0.85302(19) 0.0386 1.0000 Uani . . . . . . O10 O 0.31925(15) -0.0541(3) 0.87296(11) 0.0318 1.0000 Uani . . . . . . C11 C 0.2967(2) -0.0576(5) 0.91227(16) 0.0303 1.0000 Uani . . . . . . C12 C 0.3217(2) 0.0684(5) 0.93942(15) 0.0276 1.0000 Uani . . . . . . C13 C 0.2980(2) 0.1966(5) 0.91252(16) 0.0287 1.0000 Uani . . . . . . N14 N 0.32552(17) 0.3229(4) 0.93801(13) 0.0279 1.0000 Uani . . . . . . C15 C 0.2939(2) 0.3782(5) 0.97004(17) 0.0303 1.0000 Uani . . . . . . C16 C 0.3262(2) 0.4868(5) 1.00141(17) 0.0299 1.0000 Uani . . . . . . C17 C 0.3106(2) 0.6235(5) 0.99356(18) 0.0335 1.0000 Uani . . . . . . C18 C 0.3390(2) 0.7235(5) 1.02294(19) 0.0393 1.0000 Uani . . . . . . C19 C 0.3833(2) 0.6882(6) 1.0596(2) 0.0416 1.0000 Uani . . . . . . C20 C 0.3987(2) 0.5525(6) 1.06859(19) 0.0416 1.0000 Uani . . . . . . C21 C 0.3695(2) 0.4526(6) 1.03948(17) 0.0342 1.0000 Uani . . . . . . C22 C 0.3341(2) 0.4349(5) 0.90700(17) 0.0339 1.0000 Uani . . . . . . C23 C 0.3671(2) 0.3889(5) 0.87520(17) 0.0336 1.0000 Uani . . . . . . C24 C 0.4247(2) 0.3604(6) 0.89024(18) 0.0406 1.0000 Uani . . . . . . C25 C 0.4536(3) 0.3183(7) 0.8600(2) 0.0509 1.0000 Uani . . . . . . C26 C 0.4258(3) 0.3055(7) 0.8147(2) 0.0494 1.0000 Uani . . . . . . C27 C 0.3677(3) 0.3327(7) 0.79940(19) 0.0493 1.0000 Uani . . . . . . C28 C 0.3391(3) 0.3737(7) 0.82972(18) 0.0450 1.0000 Uani . . . . . . C29 C 0.2330(2) 0.2016(6) 0.89811(18) 0.0355 1.0000 Uani . . . . . . C30 C 0.2097(2) 0.0742(6) 0.86965(19) 0.0416 1.0000 Uani . . . . . . C31 C 0.2322(2) -0.0559(6) 0.89589(19) 0.0389 1.0000 Uani . . . . . . O32 O 0.30636(14) 0.0630(4) 0.98055(11) 0.0319 1.0000 Uani . . . . . . O33 O 0.31261(19) -0.2815(4) 0.86531(14) 0.0470 1.0000 Uani . . . . . . Cl34 Cl 0.39094(8) -0.0357(2) 0.81312(5) 0.0603 1.0000 Uani . . . . . . Cl35 Cl 0.35317(18) -0.3024(2) 0.78750(10) 0.1395 1.0000 Uani . . . . . . Cl36 Cl 0.27317(9) -0.0764(5) 0.77140(6) 0.1389 1.0000 Uani . . . . . . H111 H 0.3110 -0.1390 0.9303 0.0375 1.0000 Uiso R . . . . . H121 H 0.3631 0.0680 0.9460 0.0339 1.0000 Uiso R . . . . . H131 H 0.3111 0.1930 0.8855 0.0335 1.0000 Uiso R . . . . . H151 H 0.2884 0.3016 0.9879 0.0365 1.0000 Uiso R . . . . . H152 H 0.2574 0.4127 0.9525 0.0368 1.0000 Uiso R . . . . . H171 H 0.2802 0.6475 0.9685 0.0409 1.0000 Uiso R . . . . . H181 H 0.3271 0.8137 1.0174 0.0498 1.0000 Uiso R . . . . . H191 H 0.4037 0.7565 1.0785 0.0505 1.0000 Uiso R . . . . . H201 H 0.4281 0.5287 1.0934 0.0491 1.0000 Uiso R . . . . . H211 H 0.3792 0.3611 1.0456 0.0418 1.0000 Uiso R . . . . . H221 H 0.3548 0.5081 0.9254 0.0409 1.0000 Uiso R . . . . . H222 H 0.2972 0.4670 0.8898 0.0408 1.0000 Uiso R . . . . . H241 H 0.4433 0.3683 0.9209 0.0481 1.0000 Uiso R . . . . . H251 H 0.4926 0.2993 0.8708 0.0630 1.0000 Uiso R . . . . . H261 H 0.4461 0.2789 0.7949 0.0627 1.0000 Uiso R . . . . . H271 H 0.3477 0.3235 0.7689 0.0581 1.0000 Uiso R . . . . . H281 H 0.3002 0.3900 0.8194 0.0531 1.0000 Uiso R . . . . . H291 H 0.2192 0.2026 0.9245 0.0411 1.0000 Uiso R . . . . . H292 H 0.2202 0.2834 0.8807 0.0408 1.0000 Uiso R . . . . . H301 H 0.1680 0.0733 0.8615 0.0468 1.0000 Uiso R . . . . . H302 H 0.2214 0.0760 0.8425 0.0469 1.0000 Uiso R . . . . . H311 H 0.2184 -0.0610 0.9222 0.0473 1.0000 Uiso R . . . . . H312 H 0.2191 -0.1344 0.8769 0.0468 1.0000 Uiso R . . . . . H141 H 0.3600 0.2982 0.9548 0.0420 1.0000 Uiso R . . . . . H321 H 0.3361 0.0713 1.0007 0.0492 1.0000 Uiso R . . . . . C37 C 0.1213(3) 0.5411(7) 0.8291(2) 0.0515 1.0000 Uani . . . . . . C38 C 0.1243(2) 0.5097(6) 0.87831(18) 0.0388 1.0000 Uani . . . . . . O39 O 0.16847(17) 0.5049(5) 0.90708(14) 0.0505 1.0000 Uani . . . . . . O40 O 0.07369(16) 0.4890(5) 0.88269(12) 0.0476 1.0000 Uani . . . . . . Cl41 Cl 0.18793(8) 0.5926(2) 0.82451(7) 0.0693 1.0000 Uani . . . . . . Cl42 Cl 0.10547(13) 0.3838(3) 0.80009(7) 0.1066 1.0000 Uani . . . . . . Cl43 Cl 0.07252(11) 0.6695(4) 0.80775(9) 0.1316 1.0000 Uani . . . . . . Cl1 Cl 0.05028(14) 0.0371(3) 0.78752(14) 0.1419 1.0000 Uani . . . . . . H402 H 0.0759 0.4605 0.9079 0.0701 1.0000 Uiso R . . . . . C4 C 0.0000 0.116(2) 0.7500 0.2928 0.5000 Uani S T . . . . H42 H 0.0191 0.1744 0.7332 0.3820 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 C1 0.035(3) 0.056(4) 0.034(3) 0.005(3) 0.006(2) 0.001(3) Cl2 0.0351(8) 0.1039(15) 0.0631(10) 0.0179(10) 0.0156(7) -0.0069(9) C3 0.030(2) 0.038(3) 0.031(3) -0.003(2) 0.012(2) 0.005(2) O4 0.0313(18) 0.048(2) 0.0297(18) 0.0054(16) 0.0073(15) 0.0014(17) O5 0.0334(19) 0.042(2) 0.0311(19) 0.0059(16) 0.0083(15) 0.0032(16) Cl6 0.0402(7) 0.0577(9) 0.0533(9) 0.0022(7) 0.0075(6) 0.0197(7) Cl7 0.0543(9) 0.0589(10) 0.0432(8) -0.0121(7) -0.0030(7) 0.0029(8) C8 0.063(4) 0.046(3) 0.035(3) -0.009(3) 0.021(3) -0.014(3) C9 0.045(3) 0.035(3) 0.040(3) -0.008(2) 0.019(2) -0.006(2) O10 0.043(2) 0.0277(18) 0.0286(17) -0.0034(14) 0.0172(15) -0.0049(16) C11 0.035(3) 0.029(3) 0.031(2) 0.000(2) 0.017(2) 0.000(2) C12 0.026(2) 0.030(3) 0.027(2) 0.001(2) 0.0097(19) -0.001(2) C13 0.031(2) 0.027(2) 0.027(2) -0.002(2) 0.0054(19) -0.001(2) N14 0.028(2) 0.028(2) 0.029(2) 0.0004(17) 0.0098(16) 0.0005(17) C15 0.030(2) 0.031(3) 0.032(2) -0.003(2) 0.012(2) 0.003(2) C16 0.031(2) 0.030(3) 0.032(2) -0.002(2) 0.015(2) -0.002(2) C17 0.035(3) 0.034(3) 0.035(3) 0.003(2) 0.014(2) 0.002(2) C18 0.052(3) 0.025(3) 0.047(3) -0.003(2) 0.024(3) 0.001(2) C19 0.039(3) 0.039(3) 0.049(3) -0.017(3) 0.016(3) -0.008(2) C20 0.034(3) 0.047(3) 0.041(3) -0.007(3) 0.008(2) 0.006(3) C21 0.034(3) 0.032(3) 0.037(3) -0.003(2) 0.011(2) 0.008(2) C22 0.046(3) 0.026(3) 0.031(3) 0.005(2) 0.013(2) 0.003(2) C23 0.044(3) 0.027(3) 0.030(2) 0.003(2) 0.011(2) -0.003(2) C24 0.039(3) 0.051(3) 0.031(3) 0.000(2) 0.009(2) -0.011(3) C25 0.040(3) 0.064(4) 0.052(4) -0.003(3) 0.019(3) -0.006(3) C26 0.059(4) 0.053(4) 0.045(3) -0.005(3) 0.029(3) -0.005(3) C27 0.054(4) 0.064(4) 0.027(3) -0.003(3) 0.008(3) 0.008(3) C28 0.043(3) 0.062(4) 0.028(3) 0.004(3) 0.007(2) 0.010(3) C29 0.030(3) 0.036(3) 0.038(3) -0.002(2) 0.004(2) 0.003(2) C30 0.033(3) 0.046(3) 0.040(3) -0.008(3) 0.002(2) -0.001(2) C31 0.036(3) 0.042(3) 0.040(3) -0.008(2) 0.013(2) -0.008(2) O32 0.0328(18) 0.038(2) 0.0256(17) 0.0006(15) 0.0101(14) -0.0018(16) O33 0.067(3) 0.030(2) 0.053(2) -0.0023(18) 0.033(2) -0.005(2) Cl34 0.0645(10) 0.0786(12) 0.0449(8) -0.0037(8) 0.0271(8) -0.0254(9) Cl35 0.292(4) 0.0573(13) 0.134(2) -0.0427(14) 0.165(3) -0.0476(19) Cl36 0.0543(11) 0.320(5) 0.0333(9) 0.0315(17) -0.0013(8) 0.0014(19) C37 0.054(4) 0.068(4) 0.036(3) -0.004(3) 0.017(3) -0.009(3) C38 0.043(3) 0.035(3) 0.036(3) -0.004(2) 0.008(2) 0.006(2) O39 0.039(2) 0.063(3) 0.045(2) -0.002(2) 0.0058(18) 0.012(2) O40 0.039(2) 0.071(3) 0.0301(19) 0.012(2) 0.0062(16) -0.001(2) Cl41 0.0663(11) 0.0708(12) 0.0840(13) 0.0095(10) 0.0424(10) 0.0008(9) Cl42 0.152(2) 0.117(2) 0.0616(12) -0.0416(13) 0.0476(14) -0.0681(18) Cl43 0.1041(18) 0.211(3) 0.0995(17) 0.108(2) 0.0614(15) 0.098(2) Cl1 0.105(2) 0.103(2) 0.170(3) 0.001(2) -0.037(2) -0.0061(17) C4 0.15(3) 0.020(11) 0.51(8) 0.0000 -0.23(4) 0.0000 _refine_ls_extinction_method None #_oxford_refine_ls_scale 0.1977(5) 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 C1 . Cl2 . 1.757(6) yes C1 . C3 . 1.553(7) yes C1 . Cl6 . 1.777(6) yes C1 . Cl7 . 1.777(6) yes C3 . O4 . 1.261(6) yes C3 . O5 . 1.228(6) yes C8 . C9 . 1.560(8) yes C8 . Cl34 . 1.714(6) yes C8 . Cl35 . 1.746(7) yes C8 . Cl36 . 1.759(7) yes C9 . O10 . 1.320(6) yes C9 . O33 . 1.184(6) yes O10 . C11 . 1.475(5) yes C11 . C12 . 1.522(7) yes C11 . C31 . 1.516(7) yes C11 . H111 . 0.980 no C12 . C13 . 1.529(7) yes C12 . O32 . 1.429(5) yes C12 . H121 . 0.977 no C13 . N14 . 1.520(6) yes C13 . C29 . 1.526(7) yes C13 . H131 . 0.979 no N14 . C15 . 1.524(6) yes N14 . C22 . 1.514(6) yes N14 . H141 . 0.890 no C15 . C16 . 1.506(7) yes C15 . H151 . 0.966 no C15 . H152 . 0.965 no C16 . C17 . 1.398(7) yes C16 . C21 . 1.382(7) yes C17 . C18 . 1.383(7) yes C17 . H171 . 0.937 no C18 . C19 . 1.369(8) yes C18 . H181 . 0.933 no C19 . C20 . 1.391(8) yes C19 . H191 . 0.935 no C20 . C21 . 1.385(8) yes C20 . H201 . 0.919 no C21 . H211 . 0.935 no C22 . C23 . 1.512(7) yes C22 . H221 . 0.965 no C22 . H222 . 0.962 no C23 . C24 . 1.381(8) yes C23 . C28 . 1.386(7) yes C24 . C25 . 1.390(8) yes C24 . H241 . 0.930 no C25 . C26 . 1.378(9) yes C25 . H251 . 0.936 no C26 . C27 . 1.391(9) yes C26 . H261 . 0.933 no C27 . C28 . 1.383(8) yes C27 . H271 . 0.935 no C28 . H281 . 0.929 no C29 . C30 . 1.542(7) yes C29 . H291 . 0.970 no C29 . H292 . 0.967 no C30 . C31 . 1.529(8) yes C30 . H301 . 0.980 no C30 . H302 . 0.963 no C31 . H311 . 0.967 no C31 . H312 . 0.967 no O32 . H321 . 0.816 no C37 . C38 . 1.535(8) yes C37 . Cl41 . 1.755(6) yes C37 . Cl42 . 1.773(7) yes C37 . Cl43 . 1.733(7) yes C38 . O39 . 1.189(6) yes C38 . O40 . 1.302(7) yes O40 . H402 . 0.818 no Cl1 . C4 . 1.625(11) yes C4 . H42 5_556 0.980 no C4 . H42 . 0.980 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl2 . C1 . C3 . 112.3(4) yes Cl2 . C1 . Cl6 . 107.8(3) yes C3 . C1 . Cl6 . 109.9(4) yes Cl2 . C1 . Cl7 . 109.8(3) yes C3 . C1 . Cl7 . 107.3(4) yes Cl6 . C1 . Cl7 . 109.7(3) yes C1 . C3 . O4 . 115.1(4) yes C1 . C3 . O5 . 117.9(5) yes O4 . C3 . O5 . 126.9(5) yes C9 . C8 . Cl34 . 112.5(4) yes C9 . C8 . Cl35 . 109.1(4) yes Cl34 . C8 . Cl35 . 108.9(4) yes C9 . C8 . Cl36 . 105.0(4) yes Cl34 . C8 . Cl36 . 109.2(4) yes Cl35 . C8 . Cl36 . 112.2(4) yes C8 . C9 . O10 . 109.6(5) yes C8 . C9 . O33 . 122.7(5) yes O10 . C9 . O33 . 127.6(5) yes C9 . O10 . C11 . 116.3(4) yes O10 . C11 . C12 . 104.4(4) yes O10 . C11 . C31 . 109.1(4) yes C12 . C11 . C31 . 113.1(4) yes O10 . C11 . H111 . 109.3 no C12 . C11 . H111 . 109.1 no C31 . C11 . H111 . 111.6 no C11 . C12 . C13 . 109.8(4) yes C11 . C12 . O32 . 107.1(4) yes C13 . C12 . O32 . 111.1(4) yes C11 . C12 . H121 . 110.0 no C13 . C12 . H121 . 109.1 no O32 . C12 . H121 . 109.7 no C12 . C13 . N14 . 110.3(4) yes C12 . C13 . C29 . 112.8(4) yes N14 . C13 . C29 . 113.3(4) yes C12 . C13 . H131 . 105.5 no N14 . C13 . H131 . 105.4 no C29 . C13 . H131 . 108.9 no C13 . N14 . C15 . 113.3(4) yes C13 . N14 . C22 . 112.7(4) yes C15 . N14 . C22 . 110.1(4) yes C13 . N14 . H141 . 106.7 no C15 . N14 . H141 . 107.0 no C22 . N14 . H141 . 106.6 no N14 . C15 . C16 . 113.6(4) yes N14 . C15 . H151 . 106.0 no C16 . C15 . H151 . 108.5 no N14 . C15 . H152 . 108.7 no C16 . C15 . H152 . 110.2 no H151 . C15 . H152 . 109.7 no C15 . C16 . C17 . 120.1(5) yes C15 . C16 . C21 . 120.7(5) yes C17 . C16 . C21 . 119.1(5) yes C16 . C17 . C18 . 120.4(5) yes C16 . C17 . H171 . 119.9 no C18 . C17 . H171 . 119.7 no C17 . C18 . C19 . 119.6(5) yes C17 . C18 . H181 . 118.7 no C19 . C18 . H181 . 121.7 no C18 . C19 . C20 . 120.9(5) yes C18 . C19 . H191 . 119.4 no C20 . C19 . H191 . 119.7 no C19 . C20 . C21 . 119.2(5) yes C19 . C20 . H201 . 121.0 no C21 . C20 . H201 . 119.8 no C20 . C21 . C16 . 120.6(5) yes C20 . C21 . H211 . 119.7 no C16 . C21 . H211 . 119.7 no N14 . C22 . C23 . 113.2(4) yes N14 . C22 . H221 . 108.2 no C23 . C22 . H221 . 108.5 no N14 . C22 . H222 . 107.9 no C23 . C22 . H222 . 109.5 no H221 . C22 . H222 . 109.5 no C22 . C23 . C24 . 121.8(5) yes C22 . C23 . C28 . 119.5(5) yes C24 . C23 . C28 . 118.7(5) yes C23 . C24 . C25 . 120.2(5) yes C23 . C24 . H241 . 118.8 no C25 . C24 . H241 . 121.0 no C24 . C25 . C26 . 120.8(6) yes C24 . C25 . H251 . 119.2 no C26 . C25 . H251 . 120.0 no C25 . C26 . C27 . 119.3(5) yes C25 . C26 . H261 . 119.5 no C27 . C26 . H261 . 121.2 no C26 . C27 . C28 . 119.5(5) yes C26 . C27 . H271 . 121.0 no C28 . C27 . H271 . 119.5 no C23 . C28 . C27 . 121.4(5) yes C23 . C28 . H281 . 119.5 no C27 . C28 . H281 . 119.1 no C13 . C29 . C30 . 108.9(4) yes C13 . C29 . H291 . 110.0 no C30 . C29 . H291 . 109.1 no C13 . C29 . H292 . 109.4 no C30 . C29 . H292 . 110.4 no H291 . C29 . H292 . 109.0 no C29 . C30 . C31 . 110.9(4) yes C29 . C30 . H301 . 110.0 no C31 . C30 . H301 . 108.5 no C29 . C30 . H302 . 109.3 no C31 . C30 . H302 . 109.1 no H301 . C30 . H302 . 109.0 no C30 . C31 . C11 . 111.6(4) yes C30 . C31 . H311 . 109.4 no C11 . C31 . H311 . 107.4 no C30 . C31 . H312 . 109.8 no C11 . C31 . H312 . 109.1 no H311 . C31 . H312 . 109.6 no C12 . O32 . H321 . 105.7 no C38 . C37 . Cl41 . 111.0(4) yes C38 . C37 . Cl42 . 105.6(4) yes Cl41 . C37 . Cl42 . 106.4(4) yes C38 . C37 . Cl43 . 110.8(4) yes Cl41 . C37 . Cl43 . 108.4(4) yes Cl42 . C37 . Cl43 . 114.5(4) yes C37 . C38 . O39 . 121.6(5) yes C37 . C38 . O40 . 111.1(5) yes O39 . C38 . O40 . 127.3(5) yes C38 . O40 . H402 . 110.6 no H42 5_556 C4 . Cl1 . 106.2 no H42 5_556 C4 . Cl1 5_556 106.2 no Cl1 . C4 . Cl1 5_556 123.2(15) yes H42 5_556 C4 . H42 . 108.0 no Cl1 . C4 . H42 . 106.2 no Cl1 5_556 C4 . H42 . 106.2 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N14 . H141 . O5 2_657 178 0.89 1.90 2.788(2) yes O32 . H321 . O4 2_657 167 0.82 1.96 2.762(2) yes O40 . H402 . O4 3_455 174 0.82 1.74 2.554(2) yes