# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1500 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address 'Nicholas H. Evans' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; 'Christopher J. Serpell' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA. UK. ; 'Paul D. Beer' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; _publ_contact_author_name 'Paul D. Beer' _publ_contact_author_address ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; _publ_contact_author_email paul.beer@chem.ox.ac.uk _publ_section_title ; Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media ; # Attachment '- 11Cl2.cif' #============================================================================== #TrackingRef '- 11Cl2.cif' #============================================================================== data_BisChlorideCatenane _database_code_depnum_ccdc_archive 'CCDC 832250' #TrackingRef '- 11Cl2.cif' #============================================================================== _audit_creation_date 11-02-15 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 005CJS11 _chemical_name_systematic . _chemical_melting_point . # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.250 0.145 0.250 307 103 ' ' 2 0.750 -0.146 0.750 307 104 ' ' _platon_squeeze_details ; No satisfactory model could be constructed for the diffuse solvent cavity and therefore PLATON SQUEEZE was used to account for the electron density in the refinement. ; # start Validation Reply Form _vrf_PLAT026_BisChlorideCatenane ; PROBLEM: Ratio Observed / Unique Reflections too Low .... 28 Perc. RESPONSE: The crystal diffracted extremely weakly, particularly at high angle. Dispite the use of synchrotron radiation, many of the reflections were simply absent. ; # end Validation Reply Form _cell_length_a 17.303(6) _cell_length_b 9.051(3) _cell_length_c 43.048(16) _cell_angle_alpha 90 _cell_angle_beta 95.680(3) _cell_angle_gamma 90 _cell_volume 6709(4) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/n ' _symmetry_space_group_name_Hall '-P 2yac' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,-y,z+1/2 -x+1/2,y,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol 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' 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' 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' I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C71 Cl1 I1 N12 O5 # Dc = 1.25 Fooo = 2656.00 Mu = 5.74 M = 1263.22 # Found Formula = C64 H76 Cl2 N6 O16 # Dc = 1.24 FOOO = 2656.00 Mu = 1.66 M = 1256.24 _chemical_formula_sum 'C64 H76 Cl2 N6 O16' _chemical_formula_moiety '2(C32 H38 N3 O8), 2Cl' _chemical_compound_source . _chemical_formula_weight 1256.24 _cell_measurement_reflns_used 12833 _cell_measurement_theta_min 1 _cell_measurement_theta_max 32 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_min 0.030 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_max 0.150 _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2656 _exptl_absorpt_coefficient_mu 0.166 # Sheldrick geometric approximatio 0.98 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrystalClear (Rigaku, 1997--2009)' _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type Unknown _diffrn_measurement_device Serial _diffrn_radiation_monochromator 'Si(1 1 1) double-crystal monochromator' _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.68890 _diffrn_measurement_method \w-scans # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'CrystalClear (Rigaku, 1997--2009)' _computing_cell_refinement 'CrystalClear (Rigaku, 1997--2009)' _computing_data_reduction 'CrystalClear (Rigaku, 1997--2009)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_ambient_temperature 150 _diffrn_reflns_number 22082 _reflns_number_total 22082 _diffrn_reflns_av_R_equivalents 0.163 # Number of reflections without Friedels Law is 22082 # Number of reflections with Friedels Law is 22082 # Theoretical number of reflections is about 24977 _diffrn_reflns_theta_min 1.277 _diffrn_reflns_theta_max 31.716 _diffrn_measured_fraction_theta_max 0.884 _diffrn_reflns_theta_full 25.056 _diffrn_measured_fraction_theta_full 0.979 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -65 _diffrn_reflns_limit_l_max 65 _reflns_limit_h_min -25 _reflns_limit_h_max 24 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 63 _oxford_diffrn_Wilson_B_factor 3.94 _oxford_diffrn_Wilson_scale 49.08 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.71 _refine_diff_density_max 1.10 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 8353 _refine_ls_number_restraints 25 _refine_ls_number_parameters 793 _oxford_refine_ls_R_factor_ref 0.1401 _refine_ls_wR_factor_ref 0.2862 _refine_ls_goodness_of_fit_ref 0.9782 _refine_ls_shift/su_max 0.0002607 _refine_ls_shift/su_mean 0.0000277 # The values computed from all data _oxford_reflns_number_all 8353 _refine_ls_R_factor_all 0.1401 _refine_ls_wR_factor_all 0.2862 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6264 _refine_ls_R_factor_gt 0.1122 _refine_ls_wR_factor_gt 0.2568 # 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 Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 66.1 100. 50.0 12.3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Rigaku Americas and Rigaku Corporation. (2009). CrystalClear (Version 2.0). Rigaku Americas, 9009 TX, USA 77381-5209. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 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. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cl1 Cl 0.77441(11) 0.7878(2) 0.41064(4) 0.0543 1.0000 Uani . . . . . . . O2 O 0.6879(3) 0.4242(5) 0.37854(10) 0.0522 1.0000 Uani . . . . . . . C3 C 0.7234(4) 0.3954(7) 0.35210(15) 0.0460 1.0000 Uani . . . . . . . C4 C 0.6971(4) 0.4510(7) 0.32245(15) 0.0487 1.0000 Uani . . . . . . . C5 C 0.7382(4) 0.4168(8) 0.29724(17) 0.0523 1.0000 Uani . . . . . . . C6 C 0.8046(4) 0.3318(8) 0.30097(16) 0.0536 1.0000 Uani . . . . . . . O7 O 0.8488(3) 0.3106(6) 0.27596(12) 0.0730 1.0000 Uani . . . . . . . C8 C 0.8499(5) 0.1645(9) 0.2626(2) 0.0700 1.0000 Uani . . . . . . . C9 C 0.9297(5) 0.1210(11) 0.25630(19) 0.0765 1.0000 Uani . . . . . . . O10 O 0.9694(4) 0.0718(8) 0.28521(15) 0.0920 1.0000 Uani . . . . . . . C11 C 1.0534(6) 0.0780(16) 0.2844(3) 0.1190 1.0000 Uani . . . . . . . C12 C 1.0817(6) 0.2394(14) 0.2888(3) 0.0994 1.0000 Uani . . . . . . . C13 C 1.1203(7) 0.3054(17) 0.2684(3) 0.1251 1.0000 Uani . . . . . . . C14 C 1.1510(8) 0.4572(18) 0.2716(4) 0.1527 1.0000 Uani . . . . . . . O15 O 1.1278(4) 0.5285(10) 0.29729(18) 0.1191 1.0000 Uani . . . . . . . C16 C 1.1761(6) 0.6393(15) 0.3079(3) 0.1117 1.0000 Uani . . . . . . . C17 C 1.1565(6) 0.6872(14) 0.3404(3) 0.1072 1.0000 Uani . . . . . . . O18 O 1.0900(4) 0.7774(7) 0.33725(14) 0.0826 1.0000 Uani . . . . . . . C19 C 1.0652(5) 0.8308(9) 0.3646(2) 0.0631 1.0000 Uani . . . . . . . C20 C 1.0009(5) 0.9258(9) 0.3606(2) 0.0661 1.0000 Uani . . . . . . . C21 C 0.9665(5) 0.9824(8) 0.38585(19) 0.0620 1.0000 Uani . . . . . . . C22 C 0.9975(5) 0.9401(8) 0.41613(18) 0.0570 1.0000 Uani . . . . . . . O23 O 0.9659(3) 0.9805(5) 0.44277(11) 0.0604 1.0000 Uani . . . . . . . C24 C 0.9050(5) 1.0891(8) 0.4402(2) 0.0659 1.0000 Uani . . . . . . . C25 C 0.8738(5) 1.1065(8) 0.4713(2) 0.0730 1.0000 Uani . . . . . . . N26 N 0.8209(3) 0.9862(6) 0.47703(14) 0.0548 1.0000 Uani . . . . . . . C27 C 0.7841(4) 0.9853(8) 0.50292(18) 0.0512 1.0000 Uani . . . . . . . O28 O 0.7974(3) 1.0743(5) 0.52419(12) 0.0603 1.0000 Uani . . . . . . . C29 C 0.7231(4) 0.8674(7) 0.50498(16) 0.0507 1.0000 Uani . . . . . . . C30 C 0.6933(4) 0.8494(8) 0.53375(16) 0.0469 1.0000 Uani . . . . . . . N31 N 0.6357(3) 0.7519(6) 0.53742(12) 0.0455 1.0000 Uani . . . . . . . C32 C 0.6055(4) 0.6710(8) 0.51306(16) 0.0474 1.0000 Uani . . . . . . . C33 C 0.6335(4) 0.6790(7) 0.48400(15) 0.0463 1.0000 Uani . . . . . . . C34 C 0.6929(4) 0.7781(7) 0.48000(16) 0.0472 1.0000 Uani . . . . . . . C35 C 0.5941(4) 0.5830(8) 0.45839(16) 0.0476 1.0000 Uani . . . . . . . O36 O 0.5371(3) 0.5083(6) 0.46369(11) 0.0553 1.0000 Uani . . . . . . . N37 N 0.6211(3) 0.5855(6) 0.43031(12) 0.0490 1.0000 Uani . . . . . . . C38 C 0.5787(4) 0.5019(9) 0.40486(16) 0.0538 1.0000 Uani . . . . . . . C39 C 0.6190(4) 0.5085(9) 0.37483(16) 0.0586 1.0000 Uani . . . . . . . C40 C 0.6091(4) 0.7315(9) 0.56871(15) 0.0574 1.0000 Uani . . . . . . . C41 C 1.0620(5) 0.8502(9) 0.4196(2) 0.0648 1.0000 Uani . . . . . . . C42 C 1.0953(5) 0.7959(10) 0.3942(2) 0.0687 1.0000 Uani . . . . . . . C43 C 0.8304(5) 0.2750(8) 0.32999(18) 0.0616 1.0000 Uani . . . . . . . C44 C 0.7890(4) 0.3069(8) 0.35553(17) 0.0576 1.0000 Uani . . . . . . . O45 O 0.5815(3) 1.1510(6) 0.50680(11) 0.0610 1.0000 Uani . U . . . . . C46 C 0.6007(4) 1.1359(7) 0.47649(15) 0.0466 1.0000 Uani . . . . . . . C47 C 0.5540(4) 1.0378(8) 0.45789(17) 0.0538 1.0000 Uani . . . . . . . C48 C 0.5673(4) 1.0138(8) 0.42715(16) 0.0535 1.0000 Uani . . . . . . . C49 C 0.6291(4) 1.0850(8) 0.41476(15) 0.0478 1.0000 Uani . . . . . . . O50 O 0.6466(3) 1.0701(5) 0.38431(11) 0.0585 1.0000 Uani . . . . . . . C51 C 0.5968(5) 0.9800(9) 0.36405(16) 0.0638 1.0000 Uani . . . . . . . C52 C 0.6306(4) 0.9763(9) 0.33273(16) 0.0618 1.0000 Uani . . . . . . . N53 N 0.7043(3) 0.8958(6) 0.33494(13) 0.0508 1.0000 Uani . . . . . . . C54 C 0.7341(4) 0.8477(8) 0.30936(16) 0.0500 1.0000 Uani . . . . . . . O55 O 0.7001(3) 0.8713(6) 0.28288(11) 0.0669 1.0000 Uani . . . . . . . C56 C 0.8092(4) 0.7648(8) 0.31287(16) 0.0469 1.0000 Uani . . . . . . . C57 C 0.8405(4) 0.6968(7) 0.34028(15) 0.0466 1.0000 Uani . . . . . . . C58 C 0.9071(4) 0.6145(8) 0.34036(17) 0.0524 1.0000 Uani . . . . . . . C59 C 0.9471(5) 0.5406(8) 0.3690(2) 0.0619 1.0000 Uani . . . . . . . O60 O 1.0033(3) 0.4545(7) 0.36585(13) 0.0755 1.0000 Uani . . . . . . . N61 N 0.9243(3) 0.5714(7) 0.39680(14) 0.0563 1.0000 Uani . . . . . . . C62 C 0.9703(5) 0.5169(9) 0.42518(19) 0.0703 1.0000 Uani . . . . . . . C63 C 0.9530(5) 0.5945(9) 0.45485(19) 0.0651 1.0000 Uani . . . . . . . O64 O 0.8932(3) 0.5177(6) 0.46823(13) 0.0671 1.0000 Uani . . . . . . . C65 C 0.8758(4) 0.5629(8) 0.49787(18) 0.0582 1.0000 Uani . . . . . . . C66 C 0.8239(4) 0.4797(8) 0.5123(2) 0.0616 1.0000 Uani . . . . . . . C67 C 0.8039(4) 0.5171(8) 0.5415(2) 0.0647 1.0000 Uani . . . . . . . C68 C 0.8367(4) 0.6419(8) 0.5571(2) 0.0564 1.0000 Uani . . . . . . . O69 O 0.8095(3) 0.6715(6) 0.58564(13) 0.0707 1.0000 Uani . . . . . . . C70 C 0.8532(5) 0.7767(10) 0.6054(2) 0.0802 1.0000 Uani . . . . . . . C71 C 0.8068(8) 0.7993(13) 0.6335(3) 0.1141 1.0000 Uani . . . . . . . O72 O 0.7443(4) 0.8964(9) 0.62249(16) 0.1075 1.0000 Uani . . . . . . . C73 C 0.6964(9) 0.9360(16) 0.6457(3) 0.1404 1.0000 Uani . . . . . . . C74 C 0.6537(7) 1.0717(16) 0.6374(3) 0.1127 1.0000 Uani . . . . . . . C75 C 0.6764(7) 1.1682(13) 0.6165(3) 0.1016 1.0000 Uani . U . . . . . C76 C 0.6392(8) 1.3204(13) 0.6099(2) 0.1095 1.0000 Uani . U . . . . . O77 O 0.6395(4) 1.3522(7) 0.57648(14) 0.0899 1.0000 Uani . U . . . . . C78 C 0.5979(5) 1.2478(8) 0.55812(17) 0.0608 1.0000 Uani . U . . . . . C79 C 0.6251(5) 1.2594(8) 0.52600(17) 0.0578 1.0000 Uani . U . . . . . C80 C 0.8888(4) 0.7240(8) 0.54281(19) 0.0581 1.0000 Uani . . . . . . . C81 C 0.9083(4) 0.6871(8) 0.51322(19) 0.0610 1.0000 Uani . . . . . . . C82 C 0.9414(4) 0.6021(8) 0.31294(19) 0.0577 1.0000 Uani . . . . . . . N83 N 0.9110(4) 0.6655(7) 0.28682(14) 0.0599 1.0000 Uani . . . . . . . C84 C 0.8468(5) 0.7456(8) 0.28612(17) 0.0579 1.0000 Uani . . . . . . . C85 C 0.9516(5) 0.6509(11) 0.25766(19) 0.0785 1.0000 Uani . . . . . . . C86 C 0.6732(5) 1.1830(8) 0.43357(17) 0.0586 1.0000 Uani . . . . . . . C87 C 0.6591(4) 1.2097(8) 0.46413(16) 0.0523 1.0000 Uani . . . . . . . Cl2 Cl 0.4893(2) 0.6826(4) 0.31885(8) 0.1296 1.0000 Uani . . . . . . . H41 H 0.6526 0.5103 0.3199 0.0580 1.0000 Uiso R . . . . . . H51 H 0.7207 0.4536 0.2774 0.0631 1.0000 Uiso R . . . . . . H81 H 0.8313 0.0934 0.2774 0.0839 1.0000 Uiso R . . . . . . H82 H 0.8156 0.1615 0.2431 0.0841 1.0000 Uiso R . . . . . . H91 H 0.9276 0.0416 0.2410 0.0929 1.0000 Uiso R . . . . . . H92 H 0.9571 0.2065 0.2479 0.0928 1.0000 Uiso R . . . . . . H111 H 1.0788 0.0165 0.3009 0.1431 1.0000 Uiso R . . . . . . H112 H 1.0670 0.0427 0.2641 0.1430 1.0000 Uiso R . . . . . . H121 H 1.0703 0.2913 0.3066 0.1200 1.0000 Uiso R . . . . . . H131 H 1.1296 0.2527 0.2503 0.1501 1.0000 Uiso R . . . . . . H142 H 1.2075 0.4520 0.2741 0.1810 1.0000 Uiso R . . . . . . H141 H 1.1340 0.5131 0.2528 0.1812 1.0000 Uiso R . . . . . . H162 H 1.2291 0.6027 0.3097 0.1340 1.0000 Uiso R . . . . . . H161 H 1.1709 0.7228 0.2936 0.1340 1.0000 Uiso R . . . . . . H172 H 1.1999 0.7411 0.3509 0.1299 1.0000 Uiso R . . . . . . H171 H 1.1451 0.6005 0.3526 0.1300 1.0000 Uiso R . . . . . . H201 H 0.9804 0.9520 0.3404 0.0779 1.0000 Uiso R . . . . . . H211 H 0.9238 1.0459 0.3830 0.0750 1.0000 Uiso R . . . . . . H241 H 0.9251 1.1829 0.4338 0.0790 1.0000 Uiso R . . . . . . H242 H 0.8635 1.0564 0.4248 0.0790 1.0000 Uiso R . . . . . . H252 H 0.9164 1.1092 0.4876 0.0889 1.0000 Uiso R . . . . . . H251 H 0.8449 1.1986 0.4709 0.0887 1.0000 Uiso R . . . . . . H301 H 0.7136 0.9059 0.5510 0.0556 1.0000 Uiso R . . . . . . H321 H 0.5650 0.6072 0.5160 0.0569 1.0000 Uiso R . . . . . . H341 H 0.7124 0.7858 0.4610 0.0560 1.0000 Uiso R . . . . . . H382 H 0.5765 0.3990 0.4114 0.0650 1.0000 Uiso R . . . . . . H381 H 0.5257 0.5409 0.4009 0.0647 1.0000 Uiso R . . . . . . H391 H 0.6310 0.6104 0.3702 0.0698 1.0000 Uiso R . . . . . . H392 H 0.5839 0.4684 0.3580 0.0699 1.0000 Uiso R . . . . . . H402 H 0.5677 0.6608 0.5676 0.0874 1.0000 Uiso R . . . . . . H401 H 0.6517 0.6963 0.5827 0.0873 1.0000 Uiso R . . . . . . H403 H 0.5907 0.8234 0.5767 0.0872 1.0000 Uiso R . . . . . . H411 H 1.0831 0.8262 0.4396 0.0779 1.0000 Uiso R . . . . . . H421 H 1.1376 0.7346 0.3971 0.0820 1.0000 Uiso R . . . . . . H431 H 0.8753 0.2175 0.3324 0.0750 1.0000 Uiso R . . . . . . H441 H 0.8062 0.2690 0.3749 0.0700 1.0000 Uiso R . . . . . . H471 H 0.5142 0.9881 0.4663 0.0649 1.0000 Uiso R . . . . . . H481 H 0.5345 0.9515 0.4149 0.0638 1.0000 Uiso R . . . . . . H511 H 0.5943 0.8821 0.3728 0.0769 1.0000 Uiso R . . . . . . H512 H 0.5450 1.0225 0.3613 0.0771 1.0000 Uiso R . . . . . . H521 H 0.6394 1.0773 0.3261 0.0750 1.0000 Uiso R . . . . . . H522 H 0.5944 0.9274 0.3175 0.0748 1.0000 Uiso R . . . . . . H571 H 0.8158 0.7063 0.3583 0.0570 1.0000 Uiso R . . . . . . H621 H 1.0250 0.5307 0.4225 0.0852 1.0000 Uiso R . . . . . . H622 H 0.9595 0.4118 0.4273 0.0847 1.0000 Uiso R . . . . . . H631 H 0.9996 0.5957 0.4695 0.0789 1.0000 Uiso R . . . . . . H632 H 0.9371 0.6952 0.4504 0.0788 1.0000 Uiso R . . . . . . H661 H 0.8016 0.3957 0.5024 0.0739 1.0000 Uiso R . . . . . . H671 H 0.7694 0.4583 0.5514 0.0779 1.0000 Uiso R . . . . . . H702 H 0.9048 0.7395 0.6122 0.0980 1.0000 Uiso R . . . . . . H701 H 0.8576 0.8699 0.5943 0.0980 1.0000 Uiso R . . . . . . H712 H 0.8395 0.8451 0.6507 0.1370 1.0000 Uiso R . . . . . . H711 H 0.7857 0.7065 0.6406 0.1370 1.0000 Uiso R . . . . . . H732 H 0.7287 0.9498 0.6655 0.1670 1.0000 Uiso R . . . . . . H731 H 0.6595 0.8561 0.6481 0.1672 1.0000 Uiso R . . . . . . H741 H 0.6073 1.0910 0.6465 0.1341 1.0000 Uiso R . . . . . . H751 H 0.7182 1.1409 0.6054 0.1212 1.0000 Uiso R . . . . . . H762 H 0.6695 1.3984 0.6221 0.1361 1.0000 Uiso R . . . . . . H761 H 0.5853 1.3199 0.6158 0.1362 1.0000 Uiso R . . . . . . H782 H 0.6126 1.1485 0.5681 0.0691 1.0000 Uiso R . . . . . . H781 H 0.5424 1.2652 0.5574 0.0697 1.0000 Uiso R . . . . . . H792 H 0.6803 1.2398 0.5270 0.0691 1.0000 Uiso R . . . . . . H791 H 0.6150 1.3574 0.5176 0.0691 1.0000 Uiso R . . . . . . H801 H 0.9117 0.8064 0.5529 0.0698 1.0000 Uiso R . . . . . . H811 H 0.9437 0.7447 0.5038 0.0728 1.0000 Uiso R . . . . . . H821 H 0.9864 0.5473 0.3131 0.0697 1.0000 Uiso R . . . . . . H841 H 0.8272 0.7892 0.2677 0.0701 1.0000 Uiso R . . . . . . H851 H 0.9261 0.7107 0.2414 0.1179 1.0000 Uiso R . . . . . . H853 H 1.0040 0.6834 0.2622 0.1179 1.0000 Uiso R . . . . . . H852 H 0.9518 0.5496 0.2510 0.1178 1.0000 Uiso R . . . . . . H861 H 0.7144 1.2317 0.4254 0.0700 1.0000 Uiso R . . . . . . H871 H 0.6891 1.2773 0.4761 0.0629 1.0000 Uiso R . . . . . . H371 H 0.6654 0.6241 0.4278 0.0589 1.0000 Uiso R . . . . . . H261 H 0.8004 0.9389 0.4613 0.0649 1.0000 Uiso R . . . . . . H611 H 0.8873 0.6374 0.3985 0.0695 1.0000 Uiso R . . . . . . H531 H 0.7299 0.8811 0.3532 0.0618 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0672(11) 0.0494(10) 0.0467(10) 0.0021(8) 0.0073(8) -0.0043(9) O2 0.061(3) 0.053(3) 0.045(3) 0.003(2) 0.014(2) -0.003(2) C3 0.056(4) 0.042(4) 0.041(4) 0.000(3) 0.011(3) -0.011(3) C4 0.056(4) 0.042(4) 0.049(4) -0.004(3) 0.011(3) -0.005(3) C5 0.052(4) 0.048(4) 0.057(4) 0.001(3) 0.006(3) -0.008(4) C6 0.068(5) 0.054(4) 0.041(4) -0.002(3) 0.018(4) -0.022(4) O7 0.102(4) 0.054(3) 0.069(3) -0.004(3) 0.039(3) -0.011(3) C8 0.083(6) 0.065(5) 0.064(5) 0.001(4) 0.018(4) -0.001(5) C9 0.081(6) 0.094(7) 0.056(5) -0.012(5) 0.014(4) 0.005(5) O10 0.076(4) 0.114(5) 0.084(4) 0.027(4) 0.002(3) -0.001(4) C11 0.090(8) 0.135(11) 0.131(10) 0.020(8) 0.006(7) 0.004(8) C12 0.089(7) 0.124(10) 0.083(7) 0.000(7) -0.005(6) 0.002(7) C13 0.102(9) 0.154(13) 0.124(10) -0.037(9) 0.036(8) -0.025(9) C14 0.119(10) 0.160(14) 0.190(14) -0.070(12) 0.070(10) -0.046(10) O15 0.082(5) 0.161(7) 0.124(6) -0.068(6) 0.055(4) -0.025(5) C16 0.089(7) 0.133(10) 0.119(9) -0.049(8) 0.040(6) -0.025(7) C17 0.064(6) 0.135(10) 0.123(9) -0.037(8) 0.011(6) -0.012(7) O18 0.085(4) 0.077(4) 0.088(4) -0.008(3) 0.022(3) 0.003(3) C19 0.065(5) 0.055(5) 0.072(6) -0.012(4) 0.021(4) -0.009(4) C20 0.073(6) 0.054(5) 0.072(5) 0.002(4) 0.012(4) -0.018(4) C21 0.063(5) 0.050(4) 0.074(5) 0.002(4) 0.011(4) -0.008(4) C22 0.067(5) 0.038(4) 0.066(5) 0.001(4) 0.004(4) -0.014(4) O23 0.067(3) 0.053(3) 0.060(3) -0.003(2) 0.003(3) -0.008(3) C24 0.079(5) 0.034(4) 0.088(6) 0.007(4) 0.023(4) -0.010(4) C25 0.096(6) 0.033(4) 0.092(6) -0.006(4) 0.019(5) -0.010(4) N26 0.066(4) 0.037(3) 0.060(4) -0.002(3) 0.003(3) -0.010(3) C27 0.055(4) 0.037(4) 0.061(5) 0.006(4) 0.006(4) -0.001(3) O28 0.074(3) 0.046(3) 0.060(3) -0.016(3) 0.000(3) -0.009(3) C29 0.058(4) 0.037(4) 0.057(4) -0.001(3) 0.004(4) 0.009(3) C30 0.044(4) 0.047(4) 0.049(4) -0.009(3) -0.001(3) 0.013(3) N31 0.040(3) 0.051(3) 0.046(3) -0.002(3) 0.006(2) -0.002(3) C32 0.039(4) 0.046(4) 0.058(4) -0.004(3) 0.010(3) 0.004(3) C33 0.048(4) 0.041(4) 0.049(4) -0.002(3) -0.001(3) 0.007(3) C34 0.050(4) 0.044(4) 0.048(4) 0.000(3) 0.001(3) -0.005(3) C35 0.050(4) 0.043(4) 0.049(4) -0.001(3) 0.003(3) 0.002(3) O36 0.054(3) 0.062(3) 0.051(3) -0.010(2) 0.011(2) -0.012(3) N37 0.050(3) 0.049(3) 0.049(3) -0.007(3) 0.010(3) -0.001(3) C38 0.038(4) 0.069(5) 0.057(4) -0.011(4) 0.017(3) -0.003(3) C39 0.063(5) 0.068(5) 0.043(4) -0.001(4) 0.000(3) -0.005(4) C40 0.054(4) 0.075(5) 0.044(4) -0.010(4) 0.013(3) -0.004(4) C41 0.059(5) 0.061(5) 0.073(5) -0.003(4) 0.002(4) -0.007(4) C42 0.058(5) 0.068(5) 0.079(6) -0.002(5) -0.001(4) -0.009(4) C43 0.064(5) 0.050(4) 0.074(6) 0.004(4) 0.024(4) -0.005(4) C44 0.066(5) 0.057(5) 0.051(4) 0.011(4) 0.015(4) -0.007(4) O45 0.071(3) 0.059(3) 0.055(3) -0.006(2) 0.017(2) -0.015(3) C46 0.054(4) 0.042(4) 0.047(4) 0.009(3) 0.023(3) -0.001(3) C47 0.060(5) 0.043(4) 0.062(5) 0.001(4) 0.022(4) -0.004(4) C48 0.061(5) 0.046(4) 0.054(4) -0.001(3) 0.008(4) 0.004(4) C49 0.050(4) 0.048(4) 0.049(4) 0.009(3) 0.024(3) 0.008(3) O50 0.077(3) 0.053(3) 0.049(3) 0.008(2) 0.023(3) -0.004(3) C51 0.076(5) 0.068(5) 0.047(4) -0.001(4) 0.004(4) 0.009(4) C52 0.066(5) 0.071(5) 0.050(4) 0.007(4) 0.013(4) 0.008(4) N53 0.055(4) 0.056(4) 0.041(3) 0.002(3) 0.005(3) 0.010(3) C54 0.056(4) 0.052(4) 0.043(4) 0.000(3) 0.013(3) -0.003(4) O55 0.075(4) 0.087(4) 0.040(3) 0.001(3) 0.007(3) 0.013(3) C56 0.041(4) 0.046(4) 0.055(4) -0.003(3) 0.012(3) 0.001(3) C57 0.055(4) 0.041(4) 0.044(4) 0.000(3) 0.006(3) -0.005(3) C58 0.051(4) 0.043(4) 0.062(5) -0.001(3) 0.004(4) -0.009(4) C59 0.064(5) 0.045(4) 0.076(6) 0.007(4) 0.000(4) -0.001(4) O60 0.074(4) 0.072(4) 0.080(4) 0.001(3) 0.002(3) 0.014(3) N61 0.062(4) 0.049(4) 0.057(4) 0.007(3) 0.001(3) -0.003(3) C62 0.077(6) 0.051(5) 0.080(6) 0.012(4) -0.008(5) 0.001(4) C63 0.071(5) 0.052(5) 0.071(5) 0.017(4) 0.000(4) -0.003(4) O64 0.053(3) 0.060(3) 0.087(4) -0.010(3) 0.000(3) -0.009(3) C65 0.064(5) 0.035(4) 0.072(5) 0.000(4) -0.008(4) -0.007(4) C66 0.049(4) 0.046(4) 0.090(6) -0.016(4) 0.007(4) -0.015(4) C67 0.054(5) 0.041(4) 0.097(6) -0.004(4) 0.001(4) -0.005(4) C68 0.034(4) 0.047(4) 0.087(6) 0.009(4) 0.000(4) -0.004(3) O69 0.066(3) 0.065(4) 0.081(4) -0.009(3) 0.004(3) -0.012(3) C70 0.082(6) 0.071(6) 0.082(6) -0.006(5) -0.018(5) -0.008(5) C71 0.151(10) 0.091(8) 0.090(8) -0.011(6) -0.041(8) 0.016(8) O72 0.104(5) 0.129(6) 0.089(5) 0.001(4) 0.006(4) 0.012(5) C73 0.176(13) 0.125(11) 0.129(11) -0.007(9) 0.056(10) 0.040(10) C74 0.124(9) 0.136(11) 0.081(7) -0.006(7) 0.023(6) 0.010(9) C75 0.110(8) 0.100(8) 0.092(7) -0.006(5) 0.001(6) 0.005(7) C76 0.138(9) 0.115(9) 0.073(3) -0.017(5) -0.006(6) 0.006(8) O77 0.113(5) 0.079(4) 0.077(3) -0.021(3) 0.010(3) -0.015(3) C78 0.078(5) 0.044(4) 0.063(3) -0.003(3) 0.018(3) -0.002(3) C79 0.071(5) 0.042(4) 0.063(3) 0.000(3) 0.016(3) -0.003(4) C80 0.051(4) 0.045(4) 0.076(5) -0.002(4) -0.007(4) -0.001(4) C81 0.056(4) 0.042(4) 0.081(6) 0.021(4) -0.012(4) -0.011(4) C82 0.048(4) 0.051(4) 0.073(5) -0.001(4) 0.003(4) 0.001(4) N83 0.057(4) 0.066(4) 0.059(4) -0.001(3) 0.015(3) 0.005(3) C84 0.067(5) 0.054(5) 0.053(4) 0.007(4) 0.008(4) -0.002(4) C85 0.056(5) 0.118(8) 0.067(5) -0.010(5) 0.034(4) 0.014(5) C86 0.068(5) 0.049(4) 0.061(5) 0.016(4) 0.017(4) -0.008(4) C87 0.048(4) 0.060(5) 0.051(4) 0.007(4) 0.014(3) -0.003(4) Cl2 0.131(3) 0.146(3) 0.114(2) 0.012(2) 0.0233(19) 0.012(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2608(4) 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 O2 . C3 . 1.371(8) yes O2 . C39 . 1.411(9) yes C3 . C4 . 1.405(9) yes C3 . C44 . 1.385(10) yes C4 . C5 . 1.390(9) yes C4 . H41 . 0.937 no C5 . C6 . 1.378(10) yes C5 . H51 . 0.938 no C6 . O7 . 1.395(8) yes C6 . C43 . 1.383(11) yes O7 . C8 . 1.442(10) yes C8 . C9 . 1.487(11) yes C8 . H81 . 0.982 no C8 . H82 . 0.981 no C9 . O10 . 1.431(10) yes C9 . H91 . 0.973 no C9 . H92 . 0.994 no O10 . C11 . 1.459(12) yes C11 . C12 . 1.547(17) yes C11 . H111 . 0.975 no C11 . H112 . 0.978 no C12 . C13 . 1.301(15) yes C12 . H121 . 0.935 no C13 . C14 . 1.475(18) yes C13 . H131 . 0.942 no C14 . O15 . 1.373(14) yes C14 . H142 . 0.974 no C14 . H141 . 0.978 no O15 . C16 . 1.356(12) yes C16 . C17 . 1.534(14) yes C16 . H162 . 0.972 no C16 . H161 . 0.972 no C17 . O18 . 1.405(12) yes C17 . H172 . 0.969 no C17 . H171 . 0.975 no O18 . C19 . 1.378(9) yes C19 . C20 . 1.404(11) yes C19 . C42 . 1.367(11) yes C20 . C21 . 1.388(11) yes C20 . H201 . 0.938 no C21 . C22 . 1.412(11) yes C21 . H211 . 0.934 no C22 . O23 . 1.368(9) yes C22 . C41 . 1.378(11) yes O23 . C24 . 1.437(9) yes C24 . C25 . 1.498(11) yes C24 . H241 . 0.969 no C24 . H242 . 0.974 no C25 . N26 . 1.459(9) yes C25 . H252 . 0.968 no C25 . H251 . 0.972 no N26 . C27 . 1.337(9) yes N26 . H261 . 0.849 no C27 . O28 . 1.224(8) yes C27 . C29 . 1.510(10) yes C29 . C30 . 1.398(9) yes C29 . C34 . 1.404(9) yes C30 . N31 . 1.351(8) yes C30 . H301 . 0.941 no N31 . C32 . 1.342(8) yes N31 . C40 . 1.478(8) yes C32 . C33 . 1.388(9) yes C32 . H321 . 0.926 no C33 . C34 . 1.387(9) yes C33 . C35 . 1.512(9) yes C34 . H341 . 0.919 no C35 . O36 . 1.236(8) yes C35 . N37 . 1.338(8) yes N37 . C38 . 1.467(9) yes N37 . H371 . 0.859 no C38 . C39 . 1.529(9) yes C38 . H382 . 0.975 no C38 . H381 . 0.982 no C39 . H391 . 0.970 no C39 . H392 . 0.968 no C40 . H402 . 0.958 no C40 . H401 . 0.960 no C40 . H403 . 0.965 no C41 . C42 . 1.375(11) yes C41 . H411 . 0.928 no C42 . H421 . 0.916 no C43 . C44 . 1.400(10) yes C43 . H431 . 0.933 no C44 . H441 . 0.924 no O45 . C46 . 1.384(8) yes O45 . C79 . 1.446(9) yes C46 . C47 . 1.398(10) yes C46 . C87 . 1.363(9) yes C47 . C48 . 1.383(10) yes C47 . H471 . 0.925 no C48 . C49 . 1.397(10) yes C48 . H481 . 0.928 no C49 . O50 . 1.381(8) yes C49 . C86 . 1.380(10) yes O50 . C51 . 1.420(9) yes C51 . C52 . 1.522(10) yes C51 . H511 . 0.966 no C51 . H512 . 0.972 no C52 . N53 . 1.464(9) yes C52 . H521 . 0.974 no C52 . H522 . 0.969 no N53 . C54 . 1.334(8) yes N53 . H531 . 0.874 no C54 . O55 . 1.249(8) yes C54 . C56 . 1.495(10) yes C56 . C57 . 1.392(9) yes C56 . C84 . 1.389(10) yes C57 . C58 . 1.373(10) yes C57 . H571 . 0.924 no C58 . C59 . 1.510(11) yes C58 . C82 . 1.377(10) yes C59 . O60 . 1.264(9) yes C59 . N61 . 1.326(10) yes N61 . C62 . 1.476(9) yes N61 . H611 . 0.884 no C62 . C63 . 1.513(11) yes C62 . H621 . 0.973 no C62 . H622 . 0.976 no C63 . O64 . 1.415(9) yes C63 . H631 . 0.975 no C63 . H632 . 0.965 no O64 . C65 . 1.401(9) yes C65 . C66 . 1.367(10) yes C65 . C81 . 1.394(10) yes C66 . C67 . 1.381(11) yes C66 . H661 . 0.935 no C67 . C68 . 1.405(11) yes C67 . H671 . 0.932 no C68 . O69 . 1.383(9) yes C68 . C80 . 1.362(10) yes O69 . C70 . 1.441(10) yes C70 . C71 . 1.532(15) yes C70 . H702 . 0.972 no C70 . H701 . 0.976 no C71 . O72 . 1.438(12) yes C71 . H712 . 0.976 no C71 . H711 . 0.976 no O72 . C73 . 1.406(13) yes C73 . C74 . 1.460(17) yes C73 . H732 . 0.982 no C73 . H731 . 0.976 no C74 . C75 . 1.343(15) yes C74 . H741 . 0.944 no C75 . C76 . 1.534(15) yes C75 . H751 . 0.937 no C76 . O77 . 1.469(12) yes C76 . H762 . 0.996 no C76 . H761 . 0.991 no O77 . C78 . 1.386(9) yes C78 . C79 . 1.508(10) yes C78 . H782 . 1.017 no C78 . H781 . 0.971 no C79 . H792 . 0.968 no C79 . H791 . 0.967 no C80 . C81 . 1.391(11) yes C80 . H801 . 0.931 no C81 . H811 . 0.928 no C82 . N83 . 1.324(9) yes C82 . H821 . 0.922 no N83 . C84 . 1.324(9) yes N83 . C85 . 1.504(9) yes C84 . H841 . 0.922 no C85 . H851 . 0.957 no C85 . H853 . 0.954 no C85 . H852 . 0.960 no C86 . C87 . 1.382(10) yes C86 . H861 . 0.935 no C87 . H871 . 0.924 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 C3 . O2 . C39 . 116.9(5) yes O2 . C3 . C4 . 123.7(6) yes O2 . C3 . C44 . 116.8(6) yes C4 . C3 . C44 . 119.5(6) yes C3 . C4 . C5 . 119.0(7) yes C3 . C4 . H41 . 119.9 no C5 . C4 . H41 . 121.0 no C4 . C5 . C6 . 121.2(7) yes C4 . C5 . H51 . 119.1 no C6 . C5 . H51 . 119.7 no C5 . C6 . O7 . 120.1(7) yes C5 . C6 . C43 . 120.2(7) yes O7 . C6 . C43 . 119.6(7) yes C6 . O7 . C8 . 117.5(6) yes O7 . C8 . C9 . 111.4(7) yes O7 . C8 . H81 . 109.0 no C9 . C8 . H81 . 108.4 no O7 . C8 . H82 . 109.6 no C9 . C8 . H82 . 109.2 no H81 . C8 . H82 . 109.2 no C8 . C9 . O10 . 107.3(7) yes C8 . C9 . H91 . 110.3 no O10 . C9 . H91 . 109.9 no C8 . C9 . H92 . 110.2 no O10 . C9 . H92 . 110.6 no H91 . C9 . H92 . 108.5 no C9 . O10 . C11 . 111.1(7) yes O10 . C11 . C12 . 109.7(10) yes O10 . C11 . H111 . 109.8 no C12 . C11 . H111 . 109.5 no O10 . C11 . H112 . 109.8 no C12 . C11 . H112 . 108.5 no H111 . C11 . H112 . 109.5 no C11 . C12 . C13 . 121.8(12) yes C11 . C12 . H121 . 119.1 no C13 . C12 . H121 . 119.1 no C12 . C13 . C14 . 124.6(13) yes C12 . C13 . H131 . 118.0 no C14 . C13 . H131 . 117.4 no C13 . C14 . O15 . 112.5(12) yes C13 . C14 . H142 . 108.3 no O15 . C14 . H142 . 107.9 no C13 . C14 . H141 . 109.1 no O15 . C14 . H141 . 109.7 no H142 . C14 . H141 . 109.3 no C14 . O15 . C16 . 113.5(8) yes O15 . C16 . C17 . 109.3(9) yes O15 . C16 . H162 . 108.7 no C17 . C16 . H162 . 108.5 no O15 . C16 . H161 . 110.3 no C17 . C16 . H161 . 110.0 no H162 . C16 . H161 . 110.0 no C16 . C17 . O18 . 109.2(10) yes C16 . C17 . H172 . 109.7 no O18 . C17 . H172 . 109.9 no C16 . C17 . H171 . 109.8 no O18 . C17 . H171 . 108.2 no H172 . C17 . H171 . 110.0 no C17 . O18 . C19 . 116.3(8) yes O18 . C19 . C20 . 114.9(8) yes O18 . C19 . C42 . 126.4(8) yes C20 . C19 . C42 . 118.6(7) yes C19 . C20 . C21 . 121.9(8) yes C19 . C20 . H201 . 119.3 no C21 . C20 . H201 . 118.8 no C20 . C21 . C22 . 118.0(8) yes C20 . C21 . H211 . 121.3 no C22 . C21 . H211 . 120.7 no C21 . C22 . O23 . 123.7(7) yes C21 . C22 . C41 . 119.3(8) yes O23 . C22 . C41 . 117.0(7) yes C22 . O23 . C24 . 118.0(6) yes O23 . C24 . C25 . 109.3(7) yes O23 . C24 . H241 . 109.8 no C25 . C24 . H241 . 109.6 no O23 . C24 . H242 . 109.2 no C25 . C24 . H242 . 109.6 no H241 . C24 . H242 . 109.4 no C24 . C25 . N26 . 111.1(6) yes C24 . C25 . H252 . 109.6 no N26 . C25 . H252 . 109.9 no C24 . C25 . H251 . 107.9 no N26 . C25 . H251 . 108.2 no H252 . C25 . H251 . 110.0 no C25 . N26 . C27 . 120.3(6) yes C25 . N26 . H261 . 117.4 no C27 . N26 . H261 . 117.8 no N26 . C27 . O28 . 123.4(6) yes N26 . C27 . C29 . 116.5(6) yes O28 . C27 . C29 . 120.1(7) yes C27 . C29 . C30 . 117.1(6) yes C27 . C29 . C34 . 124.8(6) yes C30 . C29 . C34 . 118.0(6) yes C29 . C30 . N31 . 121.4(6) yes C29 . C30 . H301 . 119.6 no N31 . C30 . H301 . 119.0 no C30 . N31 . C32 . 120.0(6) yes C30 . N31 . C40 . 119.2(6) yes C32 . N31 . C40 . 120.7(6) yes N31 . C32 . C33 . 122.1(6) yes N31 . C32 . H321 . 118.3 no C33 . C32 . H321 . 119.6 no C32 . C33 . C34 . 118.4(6) yes C32 . C33 . C35 . 117.0(6) yes C34 . C33 . C35 . 124.5(6) yes C29 . C34 . C33 . 120.1(6) yes C29 . C34 . H341 . 119.8 no C33 . C34 . H341 . 120.1 no C33 . C35 . O36 . 119.4(6) yes C33 . C35 . N37 . 118.4(6) yes O36 . C35 . N37 . 122.2(6) yes C35 . N37 . C38 . 118.2(6) yes C35 . N37 . H371 . 121.1 no C38 . N37 . H371 . 120.1 no N37 . C38 . C39 . 112.0(6) yes N37 . C38 . H382 . 107.9 no C39 . C38 . H382 . 108.5 no N37 . C38 . H381 . 109.5 no C39 . C38 . H381 . 109.6 no H382 . C38 . H381 . 109.3 no C38 . C39 . O2 . 109.5(6) yes C38 . C39 . H391 . 109.6 no O2 . C39 . H391 . 110.0 no C38 . C39 . H392 . 108.2 no O2 . C39 . H392 . 110.0 no H391 . C39 . H392 . 109.5 no N31 . C40 . H402 . 109.8 no N31 . C40 . H401 . 109.0 no H402 . C40 . H401 . 109.5 no N31 . C40 . H403 . 111.1 no H402 . C40 . H403 . 108.8 no H401 . C40 . H403 . 108.8 no C22 . C41 . C42 . 121.7(8) yes C22 . C41 . H411 . 118.6 no C42 . C41 . H411 . 119.7 no C41 . C42 . C19 . 120.5(8) yes C41 . C42 . H421 . 120.0 no C19 . C42 . H421 . 119.5 no C6 . C43 . C44 . 119.2(7) yes C6 . C43 . H431 . 120.0 no C44 . C43 . H431 . 120.8 no C43 . C44 . C3 . 120.9(7) yes C43 . C44 . H441 . 119.3 no C3 . C44 . H441 . 119.8 no C46 . O45 . C79 . 116.5(5) yes O45 . C46 . C47 . 115.1(6) yes O45 . C46 . C87 . 125.1(6) yes C47 . C46 . C87 . 119.8(6) yes C46 . C47 . C48 . 120.4(6) yes C46 . C47 . H471 . 119.7 no C48 . C47 . H471 . 119.9 no C47 . C48 . C49 . 120.0(7) yes C47 . C48 . H481 . 119.3 no C49 . C48 . H481 . 120.8 no C48 . C49 . O50 . 124.4(7) yes C48 . C49 . C86 . 118.2(6) yes O50 . C49 . C86 . 117.3(6) yes C49 . O50 . C51 . 117.5(5) yes O50 . C51 . C52 . 107.1(6) yes O50 . C51 . H511 . 109.6 no C52 . C51 . H511 . 111.2 no O50 . C51 . H512 . 110.1 no C52 . C51 . H512 . 109.3 no H511 . C51 . H512 . 109.5 no C51 . C52 . N53 . 111.2(6) yes C51 . C52 . H521 . 109.0 no N53 . C52 . H521 . 109.0 no C51 . C52 . H522 . 109.3 no N53 . C52 . H522 . 108.5 no H521 . C52 . H522 . 109.8 no C52 . N53 . C54 . 120.9(6) yes C52 . N53 . H531 . 119.7 no C54 . N53 . H531 . 119.4 no N53 . C54 . O55 . 120.8(7) yes N53 . C54 . C56 . 118.9(6) yes O55 . C54 . C56 . 120.3(6) yes C54 . C56 . C57 . 124.7(6) yes C54 . C56 . C84 . 117.0(6) yes C57 . C56 . C84 . 118.2(6) yes C56 . C57 . C58 . 119.9(6) yes C56 . C57 . H571 . 119.7 no C58 . C57 . H571 . 120.4 no C57 . C58 . C59 . 124.0(7) yes C57 . C58 . C82 . 118.4(7) yes C59 . C58 . C82 . 117.6(7) yes C58 . C59 . O60 . 118.7(8) yes C58 . C59 . N61 . 119.4(7) yes O60 . C59 . N61 . 121.9(7) yes C59 . N61 . C62 . 119.5(7) yes C59 . N61 . H611 . 119.9 no C62 . N61 . H611 . 119.6 no N61 . C62 . C63 . 114.1(7) yes N61 . C62 . H621 . 108.1 no C63 . C62 . H621 . 108.5 no N61 . C62 . H622 . 108.1 no C63 . C62 . H622 . 108.4 no H621 . C62 . H622 . 109.5 no C62 . C63 . O64 . 109.3(7) yes C62 . C63 . H631 . 109.4 no O64 . C63 . H631 . 109.5 no C62 . C63 . H632 . 110.4 no O64 . C63 . H632 . 109.8 no H631 . C63 . H632 . 108.5 no C63 . O64 . C65 . 117.3(6) yes O64 . C65 . C66 . 117.5(6) yes O64 . C65 . C81 . 123.7(7) yes C66 . C65 . C81 . 118.8(8) yes C65 . C66 . C67 . 120.9(7) yes C65 . C66 . H661 . 120.1 no C67 . C66 . H661 . 119.0 no C66 . C67 . C68 . 120.5(7) yes C66 . C67 . H671 . 120.3 no C68 . C67 . H671 . 119.2 no C67 . C68 . O69 . 115.0(7) yes C67 . C68 . C80 . 118.4(8) yes O69 . C68 . C80 . 126.5(7) yes C68 . O69 . C70 . 116.6(6) yes O69 . C70 . C71 . 105.6(8) yes O69 . C70 . H702 . 111.2 no C71 . C70 . H702 . 110.2 no O69 . C70 . H701 . 110.2 no C71 . C70 . H701 . 110.1 no H702 . C70 . H701 . 109.5 no C70 . C71 . O72 . 104.8(8) yes C70 . C71 . H712 . 110.1 no O72 . C71 . H712 . 110.6 no C70 . C71 . H711 . 111.9 no O72 . C71 . H711 . 109.7 no H712 . C71 . H711 . 109.7 no C71 . O72 . C73 . 113.4(9) yes O72 . C73 . C74 . 111.1(11) yes O72 . C73 . H732 . 109.0 no C74 . C73 . H732 . 109.6 no O72 . C73 . H731 . 108.8 no C74 . C73 . H731 . 109.2 no H732 . C73 . H731 . 109.0 no C73 . C74 . C75 . 122.5(12) yes C73 . C74 . H741 . 119.0 no C75 . C74 . H741 . 118.4 no C74 . C75 . C76 . 124.2(12) yes C74 . C75 . H751 . 117.5 no C76 . C75 . H751 . 118.3 no C75 . C76 . O77 . 108.3(9) yes C75 . C76 . H762 . 110.6 no O77 . C76 . H762 . 108.8 no C75 . C76 . H761 . 109.7 no O77 . C76 . H761 . 110.2 no H762 . C76 . H761 . 109.3 no C76 . O77 . C78 . 111.9(7) yes O77 . C78 . C79 . 106.5(6) yes O77 . C78 . H782 . 105.5 no C79 . C78 . H782 . 111.2 no O77 . C78 . H781 . 111.3 no C79 . C78 . H781 . 111.0 no H782 . C78 . H781 . 111.2 no C78 . C79 . O45 . 106.5(6) yes C78 . C79 . H792 . 110.0 no O45 . C79 . H792 . 110.9 no C78 . C79 . H791 . 110.2 no O45 . C79 . H791 . 110.1 no H792 . C79 . H791 . 109.1 no C68 . C80 . C81 . 121.1(7) yes C68 . C80 . H801 . 119.8 no C81 . C80 . H801 . 119.2 no C65 . C81 . C80 . 120.3(7) yes C65 . C81 . H811 . 119.9 no C80 . C81 . H811 . 119.8 no C58 . C82 . N83 . 121.6(7) yes C58 . C82 . H821 . 118.2 no N83 . C82 . H821 . 120.2 no C82 . N83 . C84 . 121.2(6) yes C82 . N83 . C85 . 119.4(7) yes C84 . N83 . C85 . 119.3(7) yes C56 . C84 . N83 . 120.7(7) yes C56 . C84 . H841 . 119.9 no N83 . C84 . H841 . 119.4 no N83 . C85 . H851 . 110.0 no N83 . C85 . H853 . 108.4 no H851 . C85 . H853 . 109.5 no N83 . C85 . H852 . 110.3 no H851 . C85 . H852 . 109.7 no H853 . C85 . H852 . 108.9 no C49 . C86 . C87 . 122.1(7) yes C49 . C86 . H861 . 118.8 no C87 . C86 . H861 . 119.1 no C86 . C87 . C46 . 119.6(7) yes C86 . C87 . H871 . 120.2 no C46 . C87 . H871 . 120.2 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 C17 . H172 . C75 2_776 168 0.97 2.58 3.531(12) yes C32 . H321 . O36 2_666 163 0.93 2.30 3.195(12) yes C47 . H471 . O45 2_676 174 0.92 2.46 3.382(12) yes C70 . H702 . O60 2_766 153 0.97 2.49 3.386(12) yes C78 . H781 . O36 2_676 129 0.97 2.58 3.283(12) yes C79 . H792 . O28 . 154 0.97 2.53 3.427(12) yes C84 . H841 . O55 4_655 167 0.92 2.30 3.209(12) yes # Attachment '- 11ClPF6.cif' data_arc1618 _database_code_depnum_ccdc_archive 'CCDC 832251' #TrackingRef '- 11ClPF6.cif' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _chemical_absolute_configuration ad _exptl_crystal_thermal_history ; The material was crystallised at ambient temperature. A suitable crystal was cooled rapidly to 150K for single-crystal X-ray diffraction analysis. ; _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_special_details ; The NH hydrogen atoms were located in a difference Fourier map and their coordinates and isotropic displacement parameters subsequently refined. Other hydrogen atoms were positioned geometrically, the preferred orientations of the methyl groups having been identified by examination of the Fourier map. ; #============================================================= _cell_length_a 30.0276(3) _cell_length_b 23.8378(3) _cell_length_c 8.9679(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 6419.15(18) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,z+1/2 x+1/2,-y+1/2,z -x,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol 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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 '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' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_sum 'C64 H76 Cl F6 N6 O16 P' _chemical_formula_moiety '2(C32 H38 N3 O8), F6 P, Cl)' _chemical_compound_source 'synthesis as described' _chemical_formula_weight 1365.75 _cell_measurement_reflns_used 35133 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.24 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_max 0.58 _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2864 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.94 _diffrn_measurement_method \w _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 35133 _reflns_number_total 11638 #12903 reflections including absences _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_theta_min 5.177 _diffrn_reflns_theta_max 27.484 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.010 _diffrn_measured_fraction_theta_full 0.985 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _reflns_limit_h_min 0 _reflns_limit_h_max 38 _reflns_limit_k_min 0 _reflns_limit_k_max 30 _reflns_limit_l_min -11 _reflns_limit_l_max 9 _refine_diff_density_min -0.28 _refine_diff_density_max 0.41 _refine_ls_number_reflns 7361 _refine_ls_number_restraints 1 _refine_ls_number_parameters 864 #_refine_ls_R_factor_ref 0.0407 _refine_ls_wR_factor_ref 0.0459 _refine_ls_goodness_of_fit_ref 1.1343 #_reflns_number_all 11638 _refine_ls_R_factor_all 0.0702 _refine_ls_wR_factor_all 0.0664 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 7361 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_gt 0.0459 _refine_ls_shift/su_max 0.039408 _refine_ls_abs_structure_Flack 0.01(7) _refine_ls_abs_structure_details 'Flack, 5542 Friedel-pairs' _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.677 0.163 0.385 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 O 0.24929(9) 0.21580(10) 0.4768(3) 0.0414 1.0000 Uani C1 C 0.27454(11) 0.24683(14) 0.4077(4) 0.0296 1.0000 Uani N1 N 0.27076(10) 0.30234(12) 0.4128(4) 0.0315 1.0000 Uani C2 C 0.23464(12) 0.32826(14) 0.4978(5) 0.0358 1.0000 Uani C3 C 0.23796(12) 0.39128(14) 0.4928(4) 0.0336 1.0000 Uani O2 O 0.27641(8) 0.40661(9) 0.5757(3) 0.0336 1.0000 Uani C4 C 0.28227(12) 0.46293(13) 0.6021(4) 0.0310 1.0000 Uani C5 C 0.31594(12) 0.47759(14) 0.6976(4) 0.0359 1.0000 Uani C6 C 0.32546(11) 0.53390(14) 0.7279(5) 0.0366 1.0000 Uani C7 C 0.30050(12) 0.57519(13) 0.6570(4) 0.0334 1.0000 Uani C8 C 0.26599(13) 0.56049(14) 0.5629(4) 0.0372 1.0000 Uani C9 C 0.25672(12) 0.50439(14) 0.5345(4) 0.0333 1.0000 Uani O3 O 0.30782(8) 0.63164(9) 0.6746(3) 0.0455 1.0000 Uani C10 C 0.34510(13) 0.64928(16) 0.7597(4) 0.0406 1.0000 Uani C11 C 0.34461(13) 0.71202(16) 0.7520(4) 0.0410 1.0000 Uani O4 O 0.38011(10) 0.73165(12) 0.8441(3) 0.0523 1.0000 Uani C12 C 0.38855(15) 0.79019(17) 0.8236(5) 0.0518 1.0000 Uani C13 C 0.41139(13) 0.80304(17) 0.6788(5) 0.0478 1.0000 Uani C14 C 0.43198(13) 0.76503(18) 0.5953(5) 0.0462 1.0000 Uani C15 C 0.45691(14) 0.77917(18) 0.4571(5) 0.0470 1.0000 Uani O5 O 0.44443(8) 0.74022(11) 0.3434(3) 0.0392 1.0000 Uani C16 C 0.47175(12) 0.74791(15) 0.2155(5) 0.0381 1.0000 Uani C17 C 0.46205(13) 0.70200(14) 0.1070(4) 0.0354 1.0000 Uani O6 O 0.47730(8) 0.65098(9) 0.1748(3) 0.0397 1.0000 Uani C18 C 0.46647(11) 0.60128(14) 0.1039(4) 0.0319 1.0000 Uani C19 C 0.45181(12) 0.59770(14) -0.0426(4) 0.0337 1.0000 Uani C20 C 0.44259(12) 0.54580(15) -0.1047(4) 0.0342 1.0000 Uani C21 C 0.44789(11) 0.49721(15) -0.0186(4) 0.0298 1.0000 Uani C22 C 0.46329(11) 0.50078(15) 0.1265(4) 0.0304 1.0000 Uani C23 C 0.47236(11) 0.55321(13) 0.1886(4) 0.0299 1.0000 Uani O7 O 0.43695(8) 0.44711(9) -0.0871(3) 0.0323 1.0000 Uani C24 C 0.43880(13) 0.39799(15) 0.0046(4) 0.0390 1.0000 Uani C25 C 0.41707(13) 0.35052(15) -0.0828(4) 0.0369 1.0000 Uani N2 N 0.39526(11) 0.31311(12) 0.0221(3) 0.0315 1.0000 Uani C26 C 0.39672(11) 0.25690(14) 0.0140(4) 0.0292 1.0000 Uani O8 O 0.41898(8) 0.23022(10) -0.0773(3) 0.0391 1.0000 Uani C27 C 0.36866(11) 0.22695(13) 0.1266(4) 0.0276 1.0000 Uani C28 C 0.33680(10) 0.25298(12) 0.2152(4) 0.0286 1.0000 Uani C29 C 0.31097(11) 0.22172(13) 0.3128(4) 0.0262 1.0000 Uani C30 C 0.31706(11) 0.16464(13) 0.3210(4) 0.0275 1.0000 Uani N3 N 0.34896(9) 0.13987(11) 0.2367(3) 0.0288 1.0000 Uani C31 C 0.37445(11) 0.16963(14) 0.1436(4) 0.0290 1.0000 Uani C32 C 0.35523(13) 0.07823(14) 0.2523(5) 0.0419 1.0000 Uani O9 O 0.23671(8) 0.57452(9) -0.0046(3) 0.0372 1.0000 Uani C33 C 0.26318(12) 0.54429(14) 0.0625(4) 0.0305 1.0000 Uani N4 N 0.25936(11) 0.48836(12) 0.0613(3) 0.0322 1.0000 Uani C34 C 0.22318(12) 0.46165(14) -0.0214(5) 0.0364 1.0000 Uani C35 C 0.22396(12) 0.39869(14) -0.0030(4) 0.0338 1.0000 Uani O10 O 0.26111(8) 0.37907(9) -0.0868(3) 0.0364 1.0000 Uani C36 C 0.26815(11) 0.32239(14) -0.0934(4) 0.0299 1.0000 Uani C37 C 0.24471(12) 0.28211(14) -0.0133(4) 0.0339 1.0000 Uani C38 C 0.25504(13) 0.22545(15) -0.0299(4) 0.0345 1.0000 Uani C39 C 0.28887(12) 0.20913(14) -0.1248(4) 0.0317 1.0000 Uani C40 C 0.31192(12) 0.24905(15) -0.2072(4) 0.0350 1.0000 Uani C41 C 0.30175(12) 0.30519(15) -0.1898(4) 0.0358 1.0000 Uani O11 O 0.29760(9) 0.15215(9) -0.1302(3) 0.0389 1.0000 Uani C42 C 0.33043(13) 0.13321(14) -0.2360(4) 0.0365 1.0000 Uani C43 C 0.33356(13) 0.07019(16) -0.2185(5) 0.0429 1.0000 Uani O12 O 0.35897(10) 0.04769(11) -0.3377(3) 0.0532 1.0000 Uani C44 C 0.39897(18) 0.0220(2) -0.2993(7) 0.0830 1.0000 Uani C45 C 0.43108(17) 0.0582(2) -0.2319(7) 0.0756 1.0000 Uani C46 C 0.45123(19) 0.0570(3) -0.1039(7) 0.0795 1.0000 Uani C47 C 0.48442(19) 0.0857(3) -0.0396(8) 0.1105 1.0000 Uani O13 O 0.47677(11) 0.10946(15) 0.1065(4) 0.0699 1.0000 Uani C48 C 0.48775(15) 0.07502(18) 0.2285(8) 0.0701 1.0000 Uani C49 C 0.49148(14) 0.10889(18) 0.3691(6) 0.0563 1.0000 Uani O14 O 0.44931(9) 0.13474(10) 0.4089(4) 0.0480 1.0000 Uani C50 C 0.44649(11) 0.19289(14) 0.4053(5) 0.0341 1.0000 Uani C51 C 0.42087(13) 0.21824(15) 0.5123(5) 0.0387 1.0000 Uani C52 C 0.41521(12) 0.27669(14) 0.5108(4) 0.0343 1.0000 Uani C53 C 0.43623(11) 0.30901(14) 0.4028(4) 0.0302 1.0000 Uani C54 C 0.46200(11) 0.28267(15) 0.2962(4) 0.0318 1.0000 Uani C55 C 0.46681(12) 0.22451(15) 0.2954(4) 0.0352 1.0000 Uani O15 O 0.43400(8) 0.36629(9) 0.3970(3) 0.0323 1.0000 Uani C56 C 0.41759(12) 0.39394(15) 0.5280(4) 0.0333 1.0000 Uani C57 C 0.42727(12) 0.45550(14) 0.5189(4) 0.0329 1.0000 Uani N5 N 0.39630(10) 0.48489(12) 0.4203(3) 0.0284 1.0000 Uani C58 C 0.39439(11) 0.54087(14) 0.4264(4) 0.0290 1.0000 Uani O16 O 0.41676(8) 0.56931(10) 0.5127(3) 0.0346 1.0000 Uani C59 C 0.36207(11) 0.56889(14) 0.3229(4) 0.0260 1.0000 Uani C60 C 0.32953(11) 0.54071(12) 0.2421(4) 0.0270 1.0000 Uani C61 C 0.30030(11) 0.57017(13) 0.1517(4) 0.0279 1.0000 Uani C62 C 0.30360(11) 0.62785(14) 0.1468(4) 0.0294 1.0000 Uani N6 N 0.33572(9) 0.65501(10) 0.2239(3) 0.0269 1.0000 Uani C63 C 0.36463(11) 0.62662(14) 0.3105(4) 0.0270 1.0000 Uani C64 C 0.33852(11) 0.71707(12) 0.2123(5) 0.0347 1.0000 Uani Cl1 Cl 0.33031(3) 0.39722(3) 0.22361(11) 0.0346 1.0000 Uani P1 P 0.11159(3) 0.41131(4) 0.68959(14) 0.0449 1.0000 Uani F1 F 0.11853(15) 0.41761(17) 0.5133(4) 0.1086 1.0000 Uani F2 F 0.10647(13) 0.40287(17) 0.8606(4) 0.1046 1.0000 Uani F3 F 0.14061(11) 0.35633(11) 0.6765(5) 0.0988 1.0000 Uani F4 F 0.08381(10) 0.46645(12) 0.6907(6) 0.1155 1.0000 Uani F5 F 0.15589(8) 0.44545(12) 0.7166(4) 0.0766 1.0000 Uani F6 F 0.06778(10) 0.37718(14) 0.6621(5) 0.1032 1.0000 Uani H1 H 0.2872(12) 0.3240(15) 0.372(4) 0.024(10) 1.0000 Uiso H2 H 0.3781(10) 0.3318(13) 0.077(4) 0.022(8) 1.0000 Uiso H3 H 0.2792(10) 0.4708(12) 0.091(3) 0.026(8) 1.0000 Uiso H4 H 0.3804(12) 0.4624(15) 0.356(4) 0.033(10) 1.0000 Uiso H21 H 0.2364 0.3155 0.6039 0.0430 1.0000 Uiso H22 H 0.2055 0.3164 0.4543 0.0430 1.0000 Uiso H31 H 0.2108 0.4085 0.5383 0.0404 1.0000 Uiso H32 H 0.2410 0.4043 0.3872 0.0404 1.0000 Uiso H51 H 0.3340 0.4475 0.7465 0.0430 1.0000 Uiso H61 H 0.3497 0.5443 0.7992 0.0439 1.0000 Uiso H81 H 0.2476 0.5904 0.5149 0.0447 1.0000 Uiso H91 H 0.2318 0.4939 0.4659 0.0400 1.0000 Uiso H101 H 0.3422 0.6364 0.8654 0.0487 1.0000 Uiso H102 H 0.3733 0.6342 0.7160 0.0487 1.0000 Uiso H111 H 0.3492 0.7247 0.6468 0.0492 1.0000 Uiso H112 H 0.3155 0.7267 0.7895 0.0492 1.0000 Uiso H121 H 0.4078 0.8036 0.9072 0.0622 1.0000 Uiso H122 H 0.3595 0.8106 0.8260 0.0622 1.0000 Uiso H131 H 0.4111 0.8428 0.6429 0.0574 1.0000 Uiso H141 H 0.4307 0.7248 0.6271 0.0554 1.0000 Uiso H151 H 0.4897 0.7764 0.4761 0.0564 1.0000 Uiso H152 H 0.4493 0.8182 0.4248 0.0564 1.0000 Uiso H161 H 0.5038 0.7465 0.2451 0.0457 1.0000 Uiso H162 H 0.4651 0.7851 0.1687 0.0457 1.0000 Uiso H171 H 0.4783 0.7088 0.0113 0.0425 1.0000 Uiso H172 H 0.4293 0.6998 0.0871 0.0425 1.0000 Uiso H191 H 0.4479 0.6326 -0.1032 0.0404 1.0000 Uiso H201 H 0.4322 0.5430 -0.2103 0.0411 1.0000 Uiso H221 H 0.4679 0.4659 0.1866 0.0365 1.0000 Uiso H231 H 0.4831 0.5561 0.2939 0.0358 1.0000 Uiso H241 H 0.4705 0.3884 0.0276 0.0468 1.0000 Uiso H242 H 0.4222 0.4046 0.0998 0.0468 1.0000 Uiso H251 H 0.4403 0.3295 -0.1399 0.0443 1.0000 Uiso H252 H 0.3946 0.3663 -0.1537 0.0443 1.0000 Uiso H281 H 0.3325 0.2945 0.2084 0.0343 1.0000 Uiso H301 H 0.2981 0.1415 0.3888 0.0331 1.0000 Uiso H311 H 0.3982 0.1501 0.0850 0.0347 1.0000 Uiso H321 H 0.3796 0.0656 0.1843 0.0503 1.0000 Uiso H322 H 0.3633 0.0692 0.3578 0.0503 1.0000 Uiso H323 H 0.3269 0.0585 0.2254 0.0503 1.0000 Uiso H341 H 0.2264 0.4710 -0.1296 0.0436 1.0000 Uiso H342 H 0.1941 0.4764 0.0162 0.0436 1.0000 Uiso H351 H 0.2275 0.3886 0.1046 0.0405 1.0000 Uiso H352 H 0.1958 0.3819 -0.0422 0.0405 1.0000 Uiso H371 H 0.2204 0.2938 0.0563 0.0406 1.0000 Uiso H381 H 0.2379 0.1965 0.0271 0.0414 1.0000 Uiso H401 H 0.3357 0.2372 -0.2786 0.0420 1.0000 Uiso H411 H 0.3188 0.3339 -0.2476 0.0430 1.0000 Uiso H421 H 0.3599 0.1510 -0.2143 0.0439 1.0000 Uiso H422 H 0.3210 0.1430 -0.3397 0.0439 1.0000 Uiso H431 H 0.3483 0.0610 -0.1216 0.0515 1.0000 Uiso H432 H 0.3030 0.0536 -0.2201 0.0515 1.0000 Uiso H441 H 0.4124 0.0060 -0.3920 0.0996 1.0000 Uiso H442 H 0.3923 -0.0090 -0.2276 0.0996 1.0000 Uiso H451 H 0.4397 0.0908 -0.2958 0.0907 1.0000 Uiso H461 H 0.4390 0.0273 -0.0367 0.0955 1.0000 Uiso H471 H 0.5104 0.0597 -0.0310 0.1327 1.0000 Uiso H472 H 0.4922 0.1174 -0.1079 0.1327 1.0000 Uiso H481 H 0.5169 0.0562 0.2084 0.0842 1.0000 Uiso H482 H 0.4640 0.0460 0.2415 0.0842 1.0000 Uiso H491 H 0.5142 0.1390 0.3542 0.0675 1.0000 Uiso H492 H 0.5011 0.0837 0.4522 0.0675 1.0000 Uiso H511 H 0.4062 0.1951 0.5913 0.0465 1.0000 Uiso H521 H 0.3960 0.2951 0.5877 0.0412 1.0000 Uiso H541 H 0.4774 0.3056 0.2185 0.0381 1.0000 Uiso H551 H 0.4848 0.2058 0.2159 0.0423 1.0000 Uiso H561 H 0.4325 0.3779 0.6181 0.0400 1.0000 Uiso H562 H 0.3847 0.3881 0.5357 0.0400 1.0000 Uiso H571 H 0.4582 0.4608 0.4802 0.0395 1.0000 Uiso H572 H 0.4250 0.4720 0.6211 0.0395 1.0000 Uiso H601 H 0.3272 0.4989 0.2493 0.0325 1.0000 Uiso H621 H 0.2820 0.6499 0.0854 0.0353 1.0000 Uiso H631 H 0.3882 0.6475 0.3663 0.0325 1.0000 Uiso H641 H 0.3637 0.7310 0.2751 0.0417 1.0000 Uiso H642 H 0.3437 0.7279 0.1059 0.0417 1.0000 Uiso H643 H 0.3100 0.7341 0.2479 0.0417 1.0000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0437(15) 0.0261(12) 0.0545(17) 0.0000(12) 0.0171(13) -0.0026(11) C1 0.0324(19) 0.0245(17) 0.0319(19) 0.0021(16) -0.0001(17) -0.0010(14) N1 0.0328(17) 0.0212(15) 0.0406(18) 0.0015(14) 0.0076(15) -0.0018(12) C2 0.0275(18) 0.0293(18) 0.051(2) -0.0069(18) 0.0065(17) 0.0045(15) C3 0.0312(19) 0.0289(18) 0.041(2) -0.0062(17) -0.0030(17) 0.0000(15) O2 0.0384(14) 0.0210(12) 0.0414(15) 0.0006(10) -0.0028(12) 0.0015(10) C4 0.0342(19) 0.0246(18) 0.034(2) -0.0040(15) 0.0057(17) 0.0000(14) C5 0.0352(18) 0.0291(17) 0.043(2) 0.0095(17) 0.0021(18) 0.0016(14) C6 0.0327(18) 0.0331(17) 0.044(2) -0.0026(17) 0.0001(19) -0.0022(15) C7 0.037(2) 0.0246(18) 0.039(2) 0.0036(15) 0.0053(17) -0.0042(15) C8 0.040(2) 0.0270(18) 0.045(2) 0.0043(17) -0.0028(18) 0.0018(16) C9 0.035(2) 0.0281(18) 0.036(2) 0.0009(15) -0.0051(17) -0.0010(15) O3 0.0445(15) 0.0248(13) 0.067(2) 0.0001(13) -0.0150(15) -0.0034(11) C10 0.042(2) 0.042(2) 0.037(2) -0.0035(17) 0.0022(17) -0.0097(17) C11 0.044(2) 0.0357(19) 0.043(3) -0.0088(17) 0.0000(19) -0.0083(17) O4 0.067(2) 0.0502(17) 0.0395(17) -0.0069(13) -0.0036(15) -0.0228(15) C12 0.065(3) 0.044(2) 0.047(3) -0.017(2) 0.017(2) -0.021(2) C13 0.050(2) 0.047(2) 0.047(3) -0.014(2) 0.013(2) -0.0180(19) C14 0.041(2) 0.053(3) 0.044(3) 0.000(2) -0.004(2) -0.0113(19) C15 0.041(2) 0.057(3) 0.043(3) -0.0104(19) 0.0021(18) -0.007(2) O5 0.0378(15) 0.0477(16) 0.0321(14) -0.0093(12) 0.0031(12) -0.0002(12) C16 0.045(2) 0.0339(18) 0.036(2) -0.0021(17) 0.010(2) 0.0010(15) C17 0.041(2) 0.0293(19) 0.036(2) 0.0052(16) 0.0087(17) 0.0062(16) O6 0.0473(15) 0.0288(12) 0.0431(16) -0.0044(12) -0.0077(13) 0.0057(11) C18 0.0296(18) 0.0306(19) 0.036(2) -0.0056(16) 0.0028(16) 0.0014(15) C19 0.038(2) 0.0287(19) 0.034(2) 0.0022(15) -0.0002(17) 0.0033(15) C20 0.040(2) 0.038(2) 0.025(2) -0.0010(16) -0.0021(17) 0.0009(16) C21 0.0289(18) 0.0338(19) 0.0268(19) -0.0010(15) 0.0026(16) -0.0056(15) C22 0.0300(18) 0.0321(18) 0.029(2) 0.0065(15) 0.0022(16) -0.0041(15) C23 0.0248(17) 0.0352(18) 0.029(2) -0.0008(16) 0.0003(15) 0.0011(14) O7 0.0424(14) 0.0276(12) 0.0270(13) 0.0022(11) -0.0024(12) -0.0064(11) C24 0.051(2) 0.0300(19) 0.036(2) 0.0074(17) -0.0018(19) -0.0102(17) C25 0.050(2) 0.0316(19) 0.030(2) 0.0039(17) 0.0008(19) -0.0052(16) N2 0.0381(18) 0.0267(15) 0.0296(17) 0.0013(13) 0.0074(15) -0.0028(13) C26 0.0270(19) 0.0294(18) 0.031(2) 0.0001(16) -0.0049(16) -0.0053(14) O8 0.0405(14) 0.0343(13) 0.0424(16) -0.0007(12) 0.0121(13) -0.0002(12) C27 0.0269(18) 0.0224(16) 0.033(2) 0.0028(14) -0.0062(15) -0.0041(14) C28 0.0284(17) 0.0208(14) 0.036(2) 0.0006(16) -0.0033(17) -0.0013(13) C29 0.0247(17) 0.0231(16) 0.0306(19) -0.0023(14) -0.0008(15) -0.0016(13) C30 0.0295(18) 0.0230(17) 0.0301(19) 0.0003(14) -0.0008(15) -0.0002(14) N3 0.0304(15) 0.0208(13) 0.0351(17) 0.0004(13) 0.0026(14) 0.0000(11) C31 0.0298(19) 0.0282(17) 0.029(2) -0.0028(14) 0.0015(15) -0.0022(14) C32 0.043(2) 0.0242(18) 0.059(3) 0.0039(18) 0.0105(19) 0.0033(15) O9 0.0399(14) 0.0227(12) 0.0489(17) 0.0052(12) -0.0118(13) 0.0049(11) C33 0.033(2) 0.0240(17) 0.034(2) 0.0038(15) -0.0016(16) 0.0048(14) N4 0.0328(18) 0.0276(16) 0.0363(19) 0.0031(13) -0.0108(15) 0.0052(14) C34 0.038(2) 0.0261(18) 0.045(2) -0.0009(16) -0.0067(19) -0.0021(15) C35 0.034(2) 0.0266(18) 0.041(2) -0.0037(17) -0.0033(18) -0.0003(15) O10 0.0392(15) 0.0248(12) 0.0452(15) 0.0011(11) -0.0016(13) 0.0010(11) C36 0.0310(19) 0.0244(17) 0.034(2) 0.0014(16) -0.0101(17) -0.0009(14) C37 0.035(2) 0.0275(18) 0.039(2) -0.0021(16) -0.0040(17) 0.0006(15) C38 0.036(2) 0.034(2) 0.033(2) 0.0032(16) -0.0008(17) -0.0029(16) C39 0.035(2) 0.0262(18) 0.033(2) 0.0002(15) -0.0063(16) -0.0010(15) C40 0.0310(19) 0.0320(19) 0.042(2) 0.0038(17) -0.0025(17) 0.0005(15) C41 0.034(2) 0.0321(19) 0.041(2) 0.0094(17) -0.0048(18) -0.0072(16) O11 0.0449(15) 0.0228(12) 0.0489(17) 0.0006(11) 0.0080(13) 0.0023(11) C42 0.043(2) 0.0287(18) 0.038(2) -0.0043(16) 0.0029(18) -0.0014(16) C43 0.041(2) 0.039(2) 0.049(2) -0.0090(18) 0.002(2) 0.0033(17) O12 0.0535(18) 0.0503(16) 0.0560(19) -0.0116(14) -0.0049(15) 0.0111(14) C44 0.068(3) 0.094(4) 0.087(4) -0.016(4) -0.011(3) 0.031(3) C45 0.054(3) 0.069(3) 0.104(5) -0.040(3) 0.013(3) -0.010(3) C46 0.069(4) 0.109(5) 0.060(4) -0.022(3) 0.007(3) 0.034(3) C47 0.052(3) 0.162(6) 0.118(6) -0.099(5) 0.008(3) 0.006(4) O13 0.052(2) 0.074(2) 0.084(3) -0.037(2) -0.0076(18) 0.0134(17) C48 0.048(3) 0.039(2) 0.123(5) -0.026(3) 0.018(3) 0.0054(19) C49 0.041(2) 0.046(2) 0.082(4) 0.005(2) -0.006(2) 0.0111(19) O14 0.0487(16) 0.0273(14) 0.0678(19) 0.0027(14) 0.0073(15) -0.0022(11) C50 0.0311(19) 0.0264(18) 0.045(2) -0.0016(17) -0.0049(18) -0.0025(14) C51 0.039(2) 0.034(2) 0.043(2) 0.0092(18) 0.0008(19) -0.0075(17) C52 0.0319(19) 0.034(2) 0.037(2) 0.0021(17) -0.0007(17) -0.0024(15) C53 0.0310(18) 0.0299(18) 0.0297(19) 0.0022(16) -0.0079(17) -0.0022(15) C54 0.0287(18) 0.037(2) 0.030(2) 0.0040(16) -0.0022(16) -0.0030(15) C55 0.036(2) 0.033(2) 0.037(2) -0.0028(16) -0.0025(17) -0.0017(16) O15 0.0406(14) 0.0291(13) 0.0271(13) 0.0032(11) 0.0011(12) 0.0011(11) C56 0.038(2) 0.0331(18) 0.029(2) 0.0062(16) -0.0002(16) 0.0053(16) C57 0.038(2) 0.0303(19) 0.031(2) 0.0030(16) -0.0047(17) 0.0030(15) N5 0.0342(16) 0.0273(16) 0.0236(15) 0.0001(13) -0.0058(14) 0.0018(12) C58 0.0327(19) 0.035(2) 0.0191(18) 0.0025(15) -0.0008(16) -0.0004(15) O16 0.0389(14) 0.0323(13) 0.0327(15) -0.0011(11) -0.0063(12) -0.0001(11) C59 0.0289(18) 0.0284(18) 0.0206(18) 0.0017(14) 0.0018(15) 0.0007(14) C60 0.0317(17) 0.0204(15) 0.029(2) 0.0012(14) 0.0026(16) 0.0014(14) C61 0.0257(18) 0.0244(16) 0.034(2) 0.0014(14) 0.0014(15) 0.0030(13) C62 0.0279(18) 0.0275(17) 0.033(2) 0.0025(15) -0.0010(16) 0.0010(14) N6 0.0266(14) 0.0231(12) 0.0311(16) 0.0015(13) 0.0038(13) 0.0009(11) C63 0.0258(17) 0.0266(17) 0.0288(19) 0.0007(14) 0.0033(15) 0.0027(14) C64 0.0361(19) 0.0186(15) 0.049(2) 0.0033(17) 0.0020(18) -0.0002(13) Cl1 0.0388(5) 0.0228(4) 0.0422(5) 0.0031(4) -0.0038(5) 0.0005(4) P1 0.0400(5) 0.0313(5) 0.0634(8) 0.0013(5) -0.0069(6) -0.0038(4) F1 0.136(3) 0.126(3) 0.064(2) 0.014(2) -0.005(2) -0.019(3) F2 0.102(3) 0.152(3) 0.060(2) 0.004(2) 0.0166(18) -0.017(2) F3 0.103(2) 0.0487(15) 0.145(3) -0.0057(19) 0.017(2) 0.0199(15) F4 0.078(2) 0.0484(15) 0.220(5) 0.001(2) -0.018(3) 0.0211(14) F5 0.0479(15) 0.0762(18) 0.106(2) -0.0244(18) 0.0025(17) -0.0184(13) F6 0.0691(19) 0.090(2) 0.151(3) 0.008(2) -0.027(2) -0.0437(17) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2567(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.227(4) yes C1 . N1 . 1.329(4) yes C1 . C29 . 1.510(5) yes N1 . C2 . 1.463(5) yes N1 . H1 . 0.80(4) no C2 . C3 . 1.506(5) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C3 . O2 . 1.421(4) yes C3 . H31 . 1.000 no C3 . H32 . 1.000 no O2 . C4 . 1.375(4) yes C4 . C5 . 1.370(5) yes C4 . C9 . 1.390(5) yes C5 . C6 . 1.399(5) yes C5 . H51 . 1.000 no C6 . C7 . 1.391(5) yes C6 . H61 . 1.000 no C7 . C8 . 1.382(5) yes C7 . O3 . 1.372(4) yes C8 . C9 . 1.390(5) yes C8 . H81 . 1.000 no C9 . H91 . 1.000 no O3 . C10 . 1.419(4) yes C10 . C11 . 1.497(5) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C11 . O4 . 1.427(5) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no O4 . C12 . 1.430(5) yes C12 . C13 . 1.500(6) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C13 . C14 . 1.328(6) yes C13 . H131 . 1.000 no C14 . C15 . 1.487(6) yes C14 . H141 . 1.000 no C15 . O5 . 1.429(5) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no O5 . C16 . 1.422(5) yes C16 . C17 . 1.493(5) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . O6 . 1.435(4) yes C17 . H171 . 1.000 no C17 . H172 . 1.000 no O6 . C18 . 1.383(4) yes C18 . C19 . 1.388(5) yes C18 . C23 . 1.386(5) yes C19 . C20 . 1.384(5) yes C19 . H191 . 1.000 no C20 . C21 . 1.401(5) yes C20 . H201 . 1.000 no C21 . C22 . 1.384(5) yes C21 . O7 . 1.383(4) yes C22 . C23 . 1.395(5) yes C22 . H221 . 1.000 no C23 . H231 . 1.000 no O7 . C24 . 1.432(4) yes C24 . C25 . 1.523(5) yes C24 . H241 . 1.000 no C24 . H242 . 1.000 no C25 . N2 . 1.452(5) yes C25 . H251 . 1.000 no C25 . H252 . 1.000 no N2 . C26 . 1.343(4) yes N2 . H2 . 0.84(3) no C26 . O8 . 1.233(4) yes C26 . C27 . 1.497(5) yes C27 . C28 . 1.390(5) yes C27 . C31 . 1.386(5) yes C28 . C29 . 1.387(5) yes C28 . H281 . 1.000 no C29 . C30 . 1.375(5) yes C30 . N3 . 1.356(4) yes C30 . H301 . 1.000 no N3 . C31 . 1.337(4) yes N3 . C32 . 1.488(4) yes C31 . H311 . 1.000 no C32 . H321 . 1.000 no C32 . H322 . 1.000 no C32 . H323 . 1.000 no O9 . C33 . 1.230(4) yes C33 . N4 . 1.338(4) yes C33 . C61 . 1.505(5) yes N4 . C34 . 1.461(5) yes N4 . H3 . 0.78(3) no C34 . C35 . 1.510(5) yes C34 . H341 . 1.000 no C34 . H342 . 1.000 no C35 . O10 . 1.424(4) yes C35 . H351 . 1.000 no C35 . H352 . 1.000 no O10 . C36 . 1.369(4) yes C36 . C37 . 1.390(5) yes C36 . C41 . 1.391(5) yes C37 . C38 . 1.394(5) yes C37 . H371 . 1.000 no C38 . C39 . 1.381(5) yes C38 . H381 . 1.000 no C39 . C40 . 1.389(5) yes C39 . O11 . 1.384(4) yes C40 . C41 . 1.381(5) yes C40 . H401 . 1.000 no C41 . H411 . 1.000 no O11 . C42 . 1.441(4) yes C42 . C43 . 1.513(5) yes C42 . H421 . 1.000 no C42 . H422 . 1.000 no C43 . O12 . 1.419(5) yes C43 . H431 . 1.000 no C43 . H432 . 1.000 no O12 . C44 . 1.391(6) yes C44 . C45 . 1.427(8) yes C44 . H441 . 1.000 no C44 . H442 . 1.000 no C45 . C46 . 1.298(8) yes C45 . H451 . 1.000 no C46 . C47 . 1.340(8) yes C46 . H461 . 1.000 no C47 . O13 . 1.446(7) yes C47 . H471 . 1.000 no C47 . H472 . 1.000 no O13 . C48 . 1.407(7) yes C48 . C49 . 1.501(7) yes C48 . H481 . 1.000 no C48 . H482 . 1.000 no C49 . O14 . 1.453(5) yes C49 . H491 . 1.000 no C49 . H492 . 1.000 no O14 . C50 . 1.389(4) yes C50 . C51 . 1.370(5) yes C50 . C55 . 1.383(5) yes C51 . C52 . 1.404(5) yes C51 . H511 . 1.000 no C52 . C53 . 1.390(5) yes C52 . H521 . 1.000 no C53 . C54 . 1.381(5) yes C53 . O15 . 1.368(4) yes C54 . C55 . 1.394(5) yes C54 . H541 . 1.000 no C55 . H551 . 1.000 no O15 . C56 . 1.434(4) yes C56 . C57 . 1.498(5) yes C56 . H561 . 1.000 no C56 . H562 . 1.000 no C57 . N5 . 1.462(4) yes C57 . H571 . 1.000 no C57 . H572 . 1.000 no N5 . C58 . 1.337(5) yes N5 . H4 . 0.92(4) no C58 . O16 . 1.229(4) yes C58 . C59 . 1.500(5) yes C59 . C60 . 1.390(5) yes C59 . C63 . 1.383(5) yes C60 . C61 . 1.386(5) yes C60 . H601 . 1.000 no C61 . C62 . 1.379(5) yes C62 . N6 . 1.352(4) yes C62 . H621 . 1.000 no N6 . C63 . 1.347(4) yes N6 . C64 . 1.486(4) yes C63 . H631 . 1.000 no C64 . H641 . 1.000 no C64 . H642 . 1.000 no C64 . H643 . 1.000 no P1 . F1 . 1.602(4) yes P1 . F2 . 1.554(3) yes P1 . F3 . 1.578(3) yes P1 . F4 . 1.557(3) yes P1 . F5 . 1.578(3) yes P1 . F6 . 1.566(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . C1 . N1 . 122.0(3) yes O1 . C1 . C29 . 119.6(3) yes N1 . C1 . C29 . 118.4(3) yes C1 . N1 . C2 . 120.1(3) yes C1 . N1 . H1 . 125(3) no C2 . N1 . H1 . 115(3) no N1 . C2 . C3 . 110.9(3) yes N1 . C2 . H21 . 109.115 no C3 . C2 . H21 . 109.115 no N1 . C2 . H22 . 109.115 no C3 . C2 . H22 . 109.115 no H21 . C2 . H22 . 109.465 no C2 . C3 . O2 . 107.1(3) yes C2 . C3 . H31 . 110.055 no O2 . C3 . H31 . 110.052 no C2 . C3 . H32 . 110.055 no O2 . C3 . H32 . 110.053 no H31 . C3 . H32 . 109.466 no C3 . O2 . C4 . 116.4(3) yes O2 . C4 . C5 . 116.8(3) yes O2 . C4 . C9 . 123.3(3) yes C5 . C4 . C9 . 119.9(3) yes C4 . C5 . C6 . 121.1(3) yes C4 . C5 . H51 . 119.447 no C6 . C5 . H51 . 119.447 no C5 . C6 . C7 . 118.7(3) yes C5 . C6 . H61 . 120.658 no C7 . C6 . H61 . 120.658 no C6 . C7 . C8 . 120.3(3) yes C6 . C7 . O3 . 123.7(3) yes C8 . C7 . O3 . 116.0(3) yes C7 . C8 . C9 . 120.4(3) yes C7 . C8 . H81 . 119.796 no C9 . C8 . H81 . 119.795 no C4 . C9 . C8 . 119.6(3) yes C4 . C9 . H91 . 120.208 no C8 . C9 . H91 . 120.210 no C7 . O3 . C10 . 118.6(3) yes O3 . C10 . C11 . 105.3(3) yes O3 . C10 . H101 . 110.510 no C11 . C10 . H101 . 110.510 no O3 . C10 . H102 . 110.508 no C11 . C10 . H102 . 110.509 no H101 . C10 . H102 . 109.467 no C10 . C11 . O4 . 107.1(3) yes C10 . C11 . H111 . 110.071 no O4 . C11 . H111 . 110.071 no C10 . C11 . H112 . 110.071 no O4 . C11 . H112 . 110.072 no H111 . C11 . H112 . 109.467 no C11 . O4 . C12 . 112.2(3) yes O4 . C12 . C13 . 113.1(3) yes O4 . C12 . H121 . 108.568 no C13 . C12 . H121 . 108.568 no O4 . C12 . H122 . 108.569 no C13 . C12 . H122 . 108.570 no H121 . C12 . H122 . 109.468 no C12 . C13 . C14 . 124.2(4) yes C12 . C13 . H131 . 117.920 no C14 . C13 . H131 . 117.921 no C13 . C14 . C15 . 123.4(4) yes C13 . C14 . H141 . 118.323 no C15 . C14 . H141 . 118.324 no C14 . C15 . O5 . 108.4(3) yes C14 . C15 . H151 . 109.740 no O5 . C15 . H151 . 109.742 no C14 . C15 . H152 . 109.743 no O5 . C15 . H152 . 109.743 no H151 . C15 . H152 . 109.468 no C15 . O5 . C16 . 109.9(3) yes O5 . C16 . C17 . 108.6(3) yes O5 . C16 . H161 . 109.695 no C17 . C16 . H161 . 109.696 no O5 . C16 . H162 . 109.695 no C17 . C16 . H162 . 109.696 no H161 . C16 . H162 . 109.465 no C16 . C17 . O6 . 106.5(3) yes C16 . C17 . H171 . 110.222 no O6 . C17 . H171 . 110.223 no C16 . C17 . H172 . 110.220 no O6 . C17 . H172 . 110.222 no H171 . C17 . H172 . 109.466 no C17 . O6 . C18 . 117.2(3) yes O6 . C18 . C19 . 124.2(3) yes O6 . C18 . C23 . 115.2(3) yes C19 . C18 . C23 . 120.6(3) yes C18 . C19 . C20 . 119.9(3) yes C18 . C19 . H191 . 120.040 no C20 . C19 . H191 . 120.041 no C19 . C20 . C21 . 119.7(3) yes C19 . C20 . H201 . 120.174 no C21 . C20 . H201 . 120.175 no C20 . C21 . C22 . 120.3(3) yes C20 . C21 . O7 . 116.3(3) yes C22 . C21 . O7 . 123.4(3) yes C21 . C22 . C23 . 119.7(3) yes C21 . C22 . H221 . 120.147 no C23 . C22 . H221 . 120.146 no C22 . C23 . C18 . 119.8(3) yes C22 . C23 . H231 . 120.102 no C18 . C23 . H231 . 120.101 no C21 . O7 . C24 . 116.2(3) yes O7 . C24 . C25 . 107.2(3) yes O7 . C24 . H241 . 110.047 no C25 . C24 . H241 . 110.046 no O7 . C24 . H242 . 110.048 no C25 . C24 . H242 . 110.046 no H241 . C24 . H242 . 109.468 no C24 . C25 . N2 . 108.4(3) yes C24 . C25 . H251 . 109.732 no N2 . C25 . H251 . 109.734 no C24 . C25 . H252 . 109.733 no N2 . C25 . H252 . 109.735 no H251 . C25 . H252 . 109.467 no C25 . N2 . C26 . 124.3(3) yes C25 . N2 . H2 . 109(2) no C26 . N2 . H2 . 125(2) no N2 . C26 . O8 . 124.6(3) yes N2 . C26 . C27 . 114.9(3) yes O8 . C26 . C27 . 120.5(3) yes C26 . C27 . C28 . 124.1(3) yes C26 . C27 . C31 . 118.3(3) yes C28 . C27 . C31 . 117.6(3) yes C27 . C28 . C29 . 120.4(3) yes C27 . C28 . H281 . 119.804 no C29 . C28 . H281 . 119.804 no C1 . C29 . C28 . 123.2(3) yes C1 . C29 . C30 . 117.3(3) yes C28 . C29 . C30 . 119.4(3) yes C29 . C30 . N3 . 119.7(3) yes C29 . C30 . H301 . 120.157 no N3 . C30 . H301 . 120.157 no C30 . N3 . C31 . 121.5(3) yes C30 . N3 . C32 . 117.8(3) yes C31 . N3 . C32 . 120.7(3) yes C27 . C31 . N3 . 121.3(3) yes C27 . C31 . H311 . 119.332 no N3 . C31 . H311 . 119.332 no N3 . C32 . H321 . 109.467 no N3 . C32 . H322 . 109.466 no H321 . C32 . H322 . 109.474 no N3 . C32 . H323 . 109.468 no H321 . C32 . H323 . 109.476 no H322 . C32 . H323 . 109.475 no O9 . C33 . N4 . 121.6(3) yes O9 . C33 . C61 . 119.9(3) yes N4 . C33 . C61 . 118.5(3) yes C33 . N4 . C34 . 120.1(3) yes C33 . N4 . H3 . 118(2) no C34 . N4 . H3 . 121(2) no N4 . C34 . C35 . 111.5(3) yes N4 . C34 . H341 . 108.969 no C35 . C34 . H341 . 108.968 no N4 . C34 . H342 . 108.970 no C35 . C34 . H342 . 108.968 no H341 . C34 . H342 . 109.465 no C34 . C35 . O10 . 106.3(3) yes C34 . C35 . H351 . 110.259 no O10 . C35 . H351 . 110.258 no C34 . C35 . H352 . 110.259 no O10 . C35 . H352 . 110.258 no H351 . C35 . H352 . 109.466 no C35 . O10 . C36 . 117.9(3) yes O10 . C36 . C37 . 125.5(3) yes O10 . C36 . C41 . 115.5(3) yes C37 . C36 . C41 . 119.0(3) yes C36 . C37 . C38 . 120.1(3) yes C36 . C37 . H371 . 119.956 no C38 . C37 . H371 . 119.955 no C37 . C38 . C39 . 120.2(3) yes C37 . C38 . H381 . 119.925 no C39 . C38 . H381 . 119.925 no C38 . C39 . C40 . 120.1(3) yes C38 . C39 . O11 . 115.9(3) yes C40 . C39 . O11 . 124.0(3) yes C39 . C40 . C41 . 119.6(3) yes C39 . C40 . H401 . 120.218 no C41 . C40 . H401 . 120.220 no C36 . C41 . C40 . 121.1(3) yes C36 . C41 . H411 . 119.462 no C40 . C41 . H411 . 119.461 no C39 . O11 . C42 . 117.4(3) yes O11 . C42 . C43 . 106.6(3) yes O11 . C42 . H421 . 110.191 no C43 . C42 . H421 . 110.191 no O11 . C42 . H422 . 110.190 no C43 . C42 . H422 . 110.189 no H421 . C42 . H422 . 109.467 no C42 . C43 . O12 . 109.3(3) yes C42 . C43 . H431 . 109.511 no O12 . C43 . H431 . 109.513 no C42 . C43 . H432 . 109.513 no O12 . C43 . H432 . 109.514 no H431 . C43 . H432 . 109.468 no C43 . O12 . C44 . 116.3(4) yes O12 . C44 . C45 . 115.0(5) yes O12 . C44 . H441 . 108.068 no C45 . C44 . H441 . 108.064 no O12 . C44 . H442 . 108.067 no C45 . C44 . H442 . 108.063 no H441 . C44 . H442 . 109.468 no C44 . C45 . C46 . 132.6(7) yes C44 . C45 . H451 . 113.710 no C46 . C45 . H451 . 113.714 no C45 . C46 . C47 . 135.8(7) yes C45 . C46 . H461 . 112.126 no C47 . C46 . H461 . 112.121 no C46 . C47 . O13 . 118.2(5) yes C46 . C47 . H471 . 107.261 no O13 . C47 . H471 . 107.264 no C46 . C47 . H472 . 107.258 no O13 . C47 . H472 . 107.258 no H471 . C47 . H472 . 109.464 no C47 . O13 . C48 . 116.0(5) yes O13 . C48 . C49 . 110.9(3) yes O13 . C48 . H481 . 109.117 no C49 . C48 . H481 . 109.114 no O13 . C48 . H482 . 109.118 no C49 . C48 . H482 . 109.115 no H481 . C48 . H482 . 109.466 no C48 . C49 . O14 . 111.7(4) yes C48 . C49 . H491 . 108.917 no O14 . C49 . H491 . 108.916 no C48 . C49 . H492 . 108.917 no O14 . C49 . H492 . 108.916 no H491 . C49 . H492 . 109.467 no C49 . O14 . C50 . 118.1(3) yes O14 . C50 . C51 . 117.3(3) yes O14 . C50 . C55 . 122.2(3) yes C51 . C50 . C55 . 120.4(3) yes C50 . C51 . C52 . 119.9(3) yes C50 . C51 . H511 . 120.029 no C52 . C51 . H511 . 120.027 no C51 . C52 . C53 . 120.1(3) yes C51 . C52 . H521 . 119.941 no C53 . C52 . H521 . 119.941 no C52 . C53 . C54 . 119.0(3) yes C52 . C53 . O15 . 123.9(3) yes C54 . C53 . O15 . 117.1(3) yes C53 . C54 . C55 . 120.9(3) yes C53 . C54 . H541 . 119.532 no C55 . C54 . H541 . 119.532 no C54 . C55 . C50 . 119.5(3) yes C54 . C55 . H551 . 120.236 no C50 . C55 . H551 . 120.237 no C53 . O15 . C56 . 116.4(3) yes O15 . C56 . C57 . 109.8(3) yes O15 . C56 . H561 . 109.387 no C57 . C56 . H561 . 109.387 no O15 . C56 . H562 . 109.388 no C57 . C56 . H562 . 109.389 no H561 . C56 . H562 . 109.467 no C56 . C57 . N5 . 112.3(3) yes C56 . C57 . H571 . 108.765 no N5 . C57 . H571 . 108.763 no C56 . C57 . H572 . 108.765 no N5 . C57 . H572 . 108.763 no H571 . C57 . H572 . 109.467 no C57 . N5 . C58 . 118.8(3) yes C57 . N5 . H4 . 115(2) no C58 . N5 . H4 . 126(2) no N5 . C58 . O16 . 123.6(3) yes N5 . C58 . C59 . 116.6(3) yes O16 . C58 . C59 . 119.8(3) yes C58 . C59 . C60 . 124.2(3) yes C58 . C59 . C63 . 117.2(3) yes C60 . C59 . C63 . 118.6(3) yes C59 . C60 . C61 . 120.3(3) yes C59 . C60 . H601 . 119.829 no C61 . C60 . H601 . 119.830 no C33 . C61 . C60 . 124.9(3) yes C33 . C61 . C62 . 116.4(3) yes C60 . C61 . C62 . 118.6(3) yes C61 . C62 . N6 . 120.8(3) yes C61 . C62 . H621 . 119.598 no N6 . C62 . H621 . 119.598 no C62 . N6 . C63 . 120.9(3) yes C62 . N6 . C64 . 118.8(3) yes C63 . N6 . C64 . 120.3(3) yes C59 . C63 . N6 . 120.7(3) yes C59 . C63 . H631 . 119.648 no N6 . C63 . H631 . 119.647 no N6 . C64 . H641 . 109.468 no N6 . C64 . H642 . 109.467 no H641 . C64 . H642 . 109.477 no N6 . C64 . H643 . 109.466 no H641 . C64 . H643 . 109.476 no H642 . C64 . H643 . 109.474 no F1 . P1 . F2 . 177.3(2) yes F1 . P1 . F3 . 86.1(2) yes F2 . P1 . F3 . 91.2(2) yes F1 . P1 . F4 . 89.8(3) yes F2 . P1 . F4 . 92.9(3) yes F3 . P1 . F4 . 175.9(3) yes F1 . P1 . F5 . 89.6(2) yes F2 . P1 . F5 . 89.9(2) yes F3 . P1 . F5 . 88.53(17) yes F4 . P1 . F5 . 90.87(17) yes F1 . P1 . F6 . 90.1(2) yes F2 . P1 . F6 . 90.3(2) yes F3 . P1 . F6 . 91.18(19) yes F4 . P1 . F6 . 89.40(19) yes F5 . P1 . F6 . 179.6(2) yes loop_ _geom_hbond_atom_site_label_d _geom_hbond_atom_site_label_h _geom_hbond_atom_site_label_a _geom_hbond_distance_dh _geom_hbond_distance_ha _geom_hbond_distance_da _geom_hbond_angle_dha _geom_hbond_publ_flag N1 H1 Cl1 0.80(4) 2.55(4) 3.345(3) 173(3) yes N2 H2 Cl1 0.84(3) 2.49(3) 3.330(3) 173(3) yes N4 H3 Cl1 0.78(3) 2.62(3) 3.373(3) 166(3) yes N5 H4 Cl1 0.92(4) 2.47(4) 3.377(3) 170(3) yes C28 H281 Cl1 1.00 2.45 3.445(3) 171 yes C60 H601 Cl1 1.00 2.44 3.424(3) 169 yes # Attachment '- 11SO4.cif' #============================================================================== #============================================================================== data_SULPHATECATENANE _database_code_depnum_ccdc_archive 'CCDC 832252' #TrackingRef '- 11SO4.cif' #============================================================================== _cell_length_a 19.6106(4) _cell_length_b 19.6106(4) _cell_length_c 31.5616(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 10511.7(4) # start Validation Reply Form _vrf_PLAT026_SULPHATECATENANE ; PROBLEM: Ratio Observed / Unique Reflections too Low .... 26 Perc. RESPONSE: The sample diffracted very weakly, and at high angles the reflections were completely absent, even when subjected to synchrotron radiation. ; # end Validation Reply Form _refine_special_details ; The structure could be solved in a variety of space groups, but it was found that P-3c1 yielded a single macrocycle which was related to its catenated partner by symmetry and gave physically reasonable thermal ellipsoids. The entire macrocycle and the sulphate anions were obtained from the initial solution, but the co-crystallised water and the hydrogen sulphate anion required iterative cycles of Fourier refinement. Due the high level of symmetry in the structure, the precise orientation of hydrogen bonds in the water cluster could not be determined and had to be modelled using partial occupancies. The hydrogen sulphate anion was more complex still. The pseudo-tetrahedron is disordered up/down with respect to the three-fold axis on which it sits. Additionally, one of the components at a slight angle to the axis, producing another level of disorder. Finally, because of the three-fold axis the location of the protonated oxygen (required to balance charge) is also disordered. Restraints were applied to the disordered hydrogensulphate to produce a physically reasonable model, and the hydrogen atom was located to prevent unfavourable charge interactions. This produced a pseudo-cube geometry comprised of the two interpenetrated tetrahedra, consistent with the experimental charge density. Hydrogen atoms on the main residue were located geometrically and refined against the data using restraints, after which they were constrainded using rides. ; _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'P -3 c 1 ' _symmetry_space_group_name_Hall '-P 3 2"c' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -y,x-y,z y,-x+y,-z -x+y,-x,z x-y,x,-z -x+y,y,z+1/2 x-y,-y,-z+1/2 x,x-y,z+1/2 -x,-x+y,-z+1/2 -y,-x,z+1/2 y,x,-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' 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' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 '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' _cell_formula_units_Z 4 # Given Formula = C64 H76 Cl1 N6 O20 S1 # Dc = 1.25 Fooo = 4473.78 Mu = 1.58 M = 658.43 # Found Formula = C64 H87.33 N6 O26.37 S1.33 # Dc = 1.33 FOOO = 4473.78 Mu = 1.41 M = 702.72 _chemical_formula_sum 'C96 H131 N9 O40 S2' _chemical_formula_moiety ; 3(C32 H38 N3 O8), H O4 S, O4 S, 8(H2 O) ; _chemical_compound_source . _chemical_formula_weight 2115.17 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_min 0.021 _exptl_crystal_size_mid 0.043 _exptl_crystal_size_max 0.061 _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 4473.777 _exptl_absorpt_coefficient_mu 0.141 # Sheldrick geometric approximatio 0.99 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrystalClear (Rigaku, 1997--2009)' _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type Unknown _diffrn_measurement_device Serial _diffrn_radiation_monochromator 'Si(1 1 1) double-crystal monochromator' _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.68890 _diffrn_measurement_method \w-scans # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'CrystalClear (Rigaku, 1997--2009)' _computing_cell_refinement 'CrystalClear (Rigaku, 1997--2009)' _computing_data_reduction 'CrystalClear (Rigaku, 1997--2009)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _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 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_ambient_temperature 150 _diffrn_reflns_number 132460 _reflns_number_total 12709 _diffrn_reflns_av_R_equivalents 0.135 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 12709 # Theoretical number of reflections is about 26350 _diffrn_reflns_theta_min 1.199 _diffrn_reflns_theta_max 32.968 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 31.649 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -49 _diffrn_reflns_limit_l_max 49 _reflns_limit_h_min -25 _reflns_limit_h_max 0 _reflns_limit_k_min 0 _reflns_limit_k_max 29 _reflns_limit_l_min 0 _reflns_limit_l_max 47 _oxford_diffrn_Wilson_B_factor 2.71 _oxford_diffrn_Wilson_scale 51.42 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.14 _refine_diff_density_max 2.23 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 3407 _refine_ls_number_restraints 998 _refine_ls_number_parameters 500 _oxford_refine_ls_R_factor_ref 0.1488 _refine_ls_wR_factor_ref 0.3538 _refine_ls_goodness_of_fit_ref 0.9790 _refine_ls_shift/su_max 0.0096631 _refine_ls_shift/su_mean 0.0002102 # The values computed from all data _oxford_reflns_number_all 3407 _refine_ls_R_factor_all 0.1488 _refine_ls_wR_factor_all 0.3538 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3244 _refine_ls_R_factor_gt 0.1447 _refine_ls_wR_factor_gt 0.3511 # 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 Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 159. 262. 152. 57.9 12.0 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Rigaku Americas and Rigaku Corporation. (2009). CrystalClear (Version 2.0). Rigaku Americas, 9009 TX, USA 77381-5209. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 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. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Sheldrick, G. M. (2008). Acta Cryst A64, 112-122. Watkin D.J. (1994). Acta Cryst, A50, 411-437. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.2217(6) 0.4714(6) 0.4011(2) 0.0633 1.0000 Uani . . . . . . . N2 N 0.2500(4) 0.4316(4) 0.37161(19) 0.0469 1.0000 Uani . . . . . . . C3 C 0.2610(4) 0.3737(5) 0.3848(2) 0.0510 1.0000 Uani . . . . . . . C4 C 0.2867(4) 0.3357(4) 0.3585(2) 0.0406 1.0000 Uani . . . . . . . C5 C 0.3008(4) 0.3595(4) 0.3161(2) 0.0377 1.0000 Uani . . . . . . . C6 C 0.2912(4) 0.4221(4) 0.3035(2) 0.0374 1.0000 Uani . . . . . . . C7 C 0.2652(4) 0.4572(4) 0.3318(3) 0.0465 1.0000 Uani . . . . . . . C8 C 0.2953(5) 0.2698(5) 0.3761(3) 0.0517 1.0000 Uani . . . . . . . O9 O 0.2641(4) 0.2412(4) 0.41026(19) 0.0814 1.0000 Uani . . . . . . . N10 N 0.3366(4) 0.2457(4) 0.35363(18) 0.0472 1.0000 Uani . . . . . . . C11 C 0.3444(6) 0.1777(5) 0.3649(3) 0.0619 1.0000 Uani . . . . . . . C12 C 0.3524(5) 0.1402(5) 0.3257(3) 0.0539 1.0000 Uani . . . . . . . O13 O 0.2837(3) 0.1172(3) 0.30007(18) 0.0601 1.0000 Uani . . . . . . . C14 C 0.2887(5) 0.1060(4) 0.2578(3) 0.0505 1.0000 Uani . . . . . . . C15 C 0.2296(5) 0.1046(5) 0.2330(3) 0.0591 1.0000 Uani . . . . . . . C16 C 0.2286(6) 0.0927(5) 0.1897(3) 0.0633 1.0000 Uani . . . . . . . C17 C 0.2857(5) 0.0806(5) 0.1708(3) 0.0614 1.0000 Uani . . . . . . . C18 C 0.3440(5) 0.0820(4) 0.1958(3) 0.0513 1.0000 Uani . . . . . . . C19 C 0.3454(5) 0.0941(4) 0.2388(2) 0.0489 1.0000 Uani . . . . . . . O20 O 0.2910(4) 0.0693(4) 0.12838(19) 0.0742 1.0000 Uani . . . . . . . C21 C 0.2281(7) 0.0597(7) 0.1012(3) 0.0929 1.0000 Uani . . . . . . . C22 C 0.2465(8) 0.0445(7) 0.0560(3) 0.1090 1.0000 Uani . U . . . . . O23 O 0.3082(5) 0.1142(4) 0.0405(2) 0.0954 1.0000 Uani . U . . . . . C24 C 0.3391(9) 0.1003(8) 0.0037(3) 0.1208 1.0000 Uani . U . . . . . C25 C 0.3958(8) 0.1786(8) -0.0199(3) 0.0980 1.0000 Uani . U . . . . . C26 C 0.3893(7) 0.2426(7) -0.0170(3) 0.0935 1.0000 Uani . U . . . . . C27 C 0.4356(9) 0.3165(8) -0.0415(4) 0.1259 1.0000 Uani . U . . . . . O28 O 0.4752(6) 0.3846(5) -0.0126(2) 0.1195 1.0000 Uani . U . . . . . C29 C 0.5410(7) 0.3921(9) 0.0049(4) 0.1165 1.0000 Uani . . . . . . . C30 C 0.5626(8) 0.4484(9) 0.0418(4) 0.1302 1.0000 Uani . . . . . . . O31 O 0.5127(5) 0.4115(4) 0.07392(18) 0.0863 1.0000 Uani . . . . . . . C32 C 0.5075(5) 0.4567(5) 0.1062(2) 0.0535 1.0000 Uani . . . . . . . C33 C 0.4660(6) 0.4938(6) 0.1026(2) 0.0716 1.0000 Uani . . . . . . . C34 C 0.4600(5) 0.5363(5) 0.1344(2) 0.0566 1.0000 Uani . . . . . . . C35 C 0.4925(4) 0.5380(4) 0.1741(2) 0.0394 1.0000 Uani . . . . . . . C36 C 0.5338(4) 0.4981(4) 0.1781(2) 0.0424 1.0000 Uani . . . . . . . C37 C 0.5422(4) 0.4583(4) 0.1445(2) 0.0479 1.0000 Uani . . . . . . . O38 O 0.4902(3) 0.5774(3) 0.20889(14) 0.0420 1.0000 Uani . . . . . . . C39 C 0.4464(4) 0.6169(4) 0.2068(2) 0.0423 1.0000 Uani . . . . . . . C40 C 0.3573(4) 0.5615(4) 0.2097(2) 0.0424 1.0000 Uani . . . . . . . N41 N 0.3352(3) 0.5252(3) 0.25133(17) 0.0365 1.0000 Uani . . . . . . . C42 C 0.3093(4) 0.4491(4) 0.2581(2) 0.0357 1.0000 Uani . . . . . . . O43 O 0.3013(3) 0.4017(3) 0.22954(15) 0.0450 1.0000 Uani . . . . . . . S101 S 0.3333 0.6667 0.32669(10) 0.0483 1.0000 Uani S T . . . . . O102 O 0.3333 0.6667 0.3709(4) 0.1042 1.0000 Uani S T . . . . . O103 O 0.3915(3) 0.6465(3) 0.30935(18) 0.0588 1.0000 Uani . . . . . . . S104 S 0.3333 0.6667 0.09335(9) 0.0572 1.0000 Uani DS TU . . . . . O105 O 0.3333 0.6667 0.14055(9) 0.0579 0.2222 Uani DS TU . . -1 . . O106 O 0.3884(4) 0.74705(11) 0.07683(10) 0.0612 0.2222 Uani D U . . -1 . . O107 O 0.2712(9) 0.5824(4) 0.0978(10) 0.0592 0.1111 Uani D U . . -2 . . O108 O 0.3022(12) 0.7191(12) 0.1061(12) 0.0580 0.1111 Uani D U . . -2 . . O109 O 0.3634(11) 0.684(2) 0.0490(3) 0.0574 0.1111 Uani D U . . -2 . . O110 O 0.4035(9) 0.6829(17) 0.1235(6) 0.0583 0.1111 Uani D U . . -2 . . O111 O 0.3622(5) 0.6094(4) 0.07762(10) 0.0612 0.2222 Uani D U . . -1 . . O112 O 0.25227(9) 0.6379(5) 0.07683(10) 0.0609 0.2222 Uani D U . . -1 . . O201 O 0.1380(8) 0.0883(8) 0.3367(4) 0.1794 1.0000 Uani . U . . . . . O202 O 0.000000(6) 0.000000(6) 0.2930(7) 0.1615 1.0000 Uani S TU . . . . . O203 O 0.1415(8) 0.0949(7) 0.4283(4) 0.1685 1.0000 Uani . U . . . . . O204 O 0.000000(6) 0.000000(6) 0.4533(7) 0.1881 1.0000 Uani S TU . 1 2 . . H11 H 0.2447 0.5258 0.3941 0.0919 1.0000 Uiso R . . . . . . H12 H 0.2354 0.4661 0.4294 0.0921 1.0000 Uiso R . . . . . . H13 H 0.1662 0.4466 0.3986 0.0922 1.0000 Uiso R . . . . . . H31 H 0.2500 0.3575 0.4129 0.0496 1.0000 Uiso R . . . . . . H51 H 0.3145 0.3331 0.2959 0.0406 1.0000 Uiso R . . . . . . H71 H 0.2592 0.4992 0.3223 0.0403 1.0000 Uiso R . . . . . . H111 H 0.3889 0.1930 0.3838 0.0653 1.0000 Uiso R . . . . . . H112 H 0.2965 0.1398 0.3796 0.0653 1.0000 Uiso R . . . . . . H121 H 0.3574 0.0948 0.3329 0.0589 1.0000 Uiso R . . . . . . H122 H 0.3996 0.1786 0.3103 0.0590 1.0000 Uiso R . . . . . . H151 H 0.1914 0.1133 0.2460 0.0643 1.0000 Uiso R . . . . . . H161 H 0.1880 0.0902 0.1734 0.0701 1.0000 Uiso R . . . . . . H181 H 0.3825 0.0748 0.1827 0.0544 1.0000 Uiso R . . . . . . H191 H 0.3830 0.0928 0.2555 0.0532 1.0000 Uiso R . . . . . . H211 H 0.2235 0.1070 0.1015 0.1079 1.0000 Uiso R . . . . . . H212 H 0.1791 0.0149 0.1107 0.1082 1.0000 Uiso R . . . . . . H221 H 0.2636 0.0055 0.0563 0.1220 1.0000 Uiso R . . . . . . H222 H 0.2011 0.0260 0.0376 0.1221 1.0000 Uiso R . . . . . . H2041 H 0.3679 0.0746 0.0129 0.1403 1.0000 Uiso R . . . . . . H2042 H 0.2971 0.0671 -0.0160 0.1400 1.0000 Uiso R . . . . . . H251 H 0.4368 0.1825 -0.0362 0.1074 1.0000 Uiso R . . . . . . H261 H 0.3536 0.2412 0.0028 0.0894 1.0000 Uiso R . . . . . . H271 H 0.4738 0.3113 -0.0590 0.1272 1.0000 Uiso R . . . . . . H272 H 0.3991 0.3233 -0.0596 0.1269 1.0000 Uiso R . . . . . . H301 H 0.6161 0.4663 0.0515 0.1432 1.0000 Uiso R . . . . . . H302 H 0.5576 0.4936 0.0328 0.1433 1.0000 Uiso R . . . . . . H331 H 0.4428 0.4927 0.0771 0.0793 1.0000 Uiso R . . . . . . H341 H 0.4338 0.5641 0.1307 0.0661 1.0000 Uiso R . . . . . . H361 H 0.5556 0.4978 0.2039 0.0394 1.0000 Uiso R . . . . . . H371 H 0.5711 0.4321 0.1477 0.0495 1.0000 Uiso R . . . . . . H391 H 0.4626 0.6532 0.2301 0.0359 1.0000 Uiso R . . . . . . H392 H 0.4596 0.6467 0.1806 0.0364 1.0000 Uiso R . . . . . . H401 H 0.3309 0.5905 0.2049 0.0370 1.0000 Uiso R . . . . . . H402 H 0.3409 0.5198 0.1889 0.0369 1.0000 Uiso R . . . . . . H291 H 0.5810 0.4137 -0.0161 0.1279 1.0000 Uiso R . . . . . . H292 H 0.5335 0.3425 0.0138 0.1279 1.0000 Uiso R . . . . . . H101 H 0.3609 0.2721 0.3318 0.0527 1.0000 Uiso R . . . . . . H411 H 0.3392 0.5534 0.2727 0.0384 1.0000 Uiso R . . . . . . H2011 H 0.1817 0.0968 0.3266 0.2045 1.0000 Uiso R . . . . . . H2012 H 0.1378 0.0899 0.3636 0.2140 0.5000 Uiso R . . . . . . H2021 H 0.0443 0.0286 0.3049 0.2395 0.5000 Uiso R . . . . . . H241 H 0.0453 0.0313 0.4431 0.1814 0.5000 Uiso R . . 1 2 . . H242 H 0.0000 0.0000 0.4802 0.1814 0.5000 Uiso RS . . 1 2 . . H2022 H 0.0000 0.0000 0.2661 0.2300 0.5000 Uiso RS . . . . . . H2013 H 0.0934 0.0593 0.3252 0.2251 0.5000 Uiso R . . . . . . H2032 H 0.1403 0.1019 0.4027 0.2146 0.5000 Uiso R . . . . . . H2033 H 0.0960 0.0637 0.4382 0.2146 0.5000 Uiso R . . . . . . H2031 H 0.1650 0.1436 0.4345 0.2146 1.0000 Uiso R . . . . . . H1071 H 0.2575 0.5705 0.1252 0.0718 0.1111 Uiso R . . . -2 . . H1111 H 0.3313 0.5633 0.0869 0.0736 0.2222 Uiso R . . . -1 . . 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 0.086(4) 0.103(5) 0.026(4) 0.011(4) 0.017(4) 0.067(4) N2 0.046(3) 0.062(4) 0.037(3) 0.015(3) 0.005(3) 0.030(3) C3 0.049(4) 0.070(5) 0.035(4) 0.020(4) 0.006(3) 0.030(4) C4 0.039(3) 0.050(4) 0.031(4) 0.009(3) 0.003(3) 0.022(3) C5 0.036(3) 0.048(4) 0.029(4) 0.008(3) -0.001(3) 0.020(3) C6 0.028(3) 0.042(4) 0.034(4) -0.002(3) -0.003(3) 0.011(3) C7 0.033(3) 0.045(4) 0.055(5) 0.006(4) -0.003(3) 0.016(3) C8 0.052(4) 0.055(4) 0.043(4) 0.023(4) 0.005(4) 0.023(4) O9 0.116(4) 0.101(4) 0.054(4) 0.045(3) 0.035(3) 0.074(3) N10 0.066(3) 0.052(4) 0.031(3) 0.012(3) 0.003(3) 0.034(3) C11 0.080(4) 0.059(4) 0.050(4) 0.015(4) 0.005(4) 0.038(4) C12 0.064(4) 0.050(4) 0.056(4) 0.011(4) 0.001(4) 0.034(4) O13 0.058(3) 0.057(3) 0.060(3) 0.010(3) 0.002(3) 0.025(3) C14 0.061(4) 0.031(4) 0.050(5) 0.006(3) -0.007(4) 0.016(3) C15 0.059(4) 0.052(4) 0.066(5) 0.000(4) -0.014(4) 0.028(4) C16 0.064(4) 0.049(4) 0.073(5) 0.006(4) -0.013(4) 0.025(4) C17 0.071(4) 0.040(4) 0.068(5) 0.003(4) -0.013(4) 0.025(4) C18 0.066(4) 0.037(4) 0.056(5) 0.001(3) -0.012(4) 0.029(3) C19 0.052(4) 0.041(4) 0.050(4) 0.004(3) -0.012(4) 0.021(3) O20 0.100(4) 0.072(4) 0.054(4) -0.013(3) -0.028(3) 0.045(3) C21 0.098(5) 0.089(6) 0.074(5) 0.002(5) -0.034(5) 0.034(5) C22 0.131(5) 0.092(5) 0.079(5) -0.004(4) -0.046(4) 0.036(4) O23 0.123(4) 0.094(4) 0.063(3) -0.008(3) -0.025(3) 0.049(3) C24 0.188(5) 0.128(4) 0.059(5) -0.014(4) -0.024(4) 0.089(4) C25 0.125(5) 0.139(4) 0.043(4) -0.023(4) -0.023(4) 0.076(4) C26 0.091(5) 0.115(4) 0.066(5) -0.007(4) 0.002(4) 0.046(4) C27 0.135(5) 0.117(4) 0.068(5) -0.009(3) -0.009(5) 0.020(5) O28 0.125(5) 0.121(4) 0.064(4) -0.011(3) -0.003(4) 0.025(4) C29 0.077(5) 0.156(7) 0.077(6) -0.049(6) 0.021(5) 0.029(5) C30 0.106(5) 0.136(7) 0.118(7) -0.047(6) 0.000(6) 0.037(6) O31 0.143(4) 0.105(4) 0.034(3) 0.003(3) 0.018(3) 0.079(4) C32 0.081(4) 0.066(4) 0.028(4) 0.000(3) 0.009(4) 0.048(4) C33 0.111(5) 0.112(5) 0.019(4) -0.006(4) -0.011(4) 0.076(5) C34 0.073(4) 0.085(5) 0.038(4) 0.004(4) -0.003(4) 0.060(4) C35 0.041(3) 0.043(4) 0.036(4) 0.009(3) 0.000(3) 0.022(3) C36 0.042(3) 0.048(4) 0.041(4) 0.012(3) 0.006(3) 0.026(3) C37 0.052(4) 0.044(4) 0.055(5) 0.022(4) 0.015(4) 0.029(3) O38 0.050(3) 0.051(3) 0.036(3) -0.004(2) -0.003(2) 0.034(2) C39 0.046(4) 0.039(4) 0.046(4) 0.007(3) 0.000(3) 0.024(3) C40 0.043(4) 0.035(4) 0.049(4) 0.002(3) -0.003(3) 0.020(3) N41 0.036(3) 0.039(3) 0.032(3) 0.003(3) 0.003(2) 0.017(3) C42 0.033(3) 0.047(4) 0.027(4) 0.000(3) -0.003(3) 0.019(3) O43 0.052(3) 0.046(3) 0.039(3) 0.002(2) -0.006(2) 0.026(2) S101 0.0556(14) 0.0556(14) 0.0336(19) 0.0000 0.0000 0.0278(7) O102 0.132(4) 0.132(4) 0.048(5) 0.0000 0.0000 0.066(2) O103 0.049(3) 0.049(3) 0.079(3) -0.018(3) -0.024(3) 0.026(2) S104 0.0675(11) 0.0675(11) 0.0365(16) 0.0000 0.0000 0.0338(5) O105 0.0687(18) 0.0687(18) 0.0365(16) 0.0000 0.0000 0.0343(9) O106 0.072(2) 0.0688(14) 0.039(2) 0.0019(17) 0.001(2) 0.0330(13) O107 0.071(2) 0.0677(14) 0.036(3) -0.002(2) 0.001(2) 0.0323(13) O108 0.069(2) 0.069(2) 0.037(3) -0.001(2) 0.000(2) 0.0351(15) O109 0.068(3) 0.069(3) 0.0364(18) -0.001(2) -0.0001(12) 0.034(2) O110 0.069(2) 0.068(3) 0.037(3) 0.001(2) -0.0013(16) 0.0344(16) O111 0.072(2) 0.071(2) 0.042(2) -0.0023(19) 0.002(2) 0.0366(15) O112 0.0693(14) 0.072(2) 0.040(2) 0.000(2) -0.0027(15) 0.0352(12) O201 0.170(4) 0.202(6) 0.151(4) -0.017(5) -0.001(4) 0.082(5) O202 0.162(4) 0.162(4) 0.161(6) 0.0000 0.0000 0.0809(19) O203 0.219(4) 0.137(5) 0.150(4) 0.003(5) -0.003(4) 0.090(5) O204 0.210(4) 0.210(4) 0.144(6) 0.0000 0.0000 0.1051(18) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.1836(4) 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 . N2 . 1.488(10) yes C1 . H11 . 0.954 no C1 . H12 . 0.955 no C1 . H13 . 0.948 no N2 . C3 . 1.326(10) yes N2 . C7 . 1.332(9) yes C3 . C4 . 1.368(11) yes C3 . H31 . 0.929 no C4 . C5 . 1.398(10) yes C4 . C8 . 1.491(11) yes C5 . C6 . 1.391(10) yes C5 . H51 . 0.940 no C6 . C7 . 1.371(10) yes C6 . C42 . 1.508(10) yes C7 . H71 . 0.937 no C8 . O9 . 1.229(9) yes C8 . N10 . 1.330(10) yes N10 . C11 . 1.459(10) yes N10 . H101 . 0.850 no C11 . C12 . 1.486(11) yes C11 . H111 . 0.973 no C11 . H112 . 0.976 no C12 . O13 . 1.436(10) yes C12 . H121 . 0.971 no C12 . H122 . 0.982 no O13 . C14 . 1.363(9) yes C14 . C15 . 1.388(11) yes C14 . C19 . 1.382(12) yes C15 . C16 . 1.386(12) yes C15 . H151 . 0.941 no C16 . C17 . 1.390(13) yes C16 . H161 . 0.929 no C17 . C18 . 1.379(12) yes C17 . O20 . 1.369(11) yes C18 . C19 . 1.376(11) yes C18 . H181 . 0.931 no C19 . H191 . 0.917 no O20 . C21 . 1.435(11) yes C21 . C22 . 1.538(16) yes C21 . H211 . 0.975 no C21 . H212 . 0.971 no C22 . O23 . 1.384(13) yes C22 . H221 . 0.975 no C22 . H222 . 0.967 no O23 . C24 . 1.398(14) yes C24 . C25 . 1.564(18) yes C24 . H2041 . 0.970 no C24 . H2042 . 0.977 no C25 . C26 . 1.328(16) yes C25 . H251 . 0.924 no C26 . C27 . 1.486(16) yes C26 . H261 . 0.930 no C27 . O28 . 1.477(14) yes C27 . H271 . 0.975 no C27 . H272 . 0.976 no O28 . C29 . 1.344(15) yes C29 . C30 . 1.511(16) yes C29 . H291 . 0.950 no C29 . H292 . 0.950 no C30 . O31 . 1.342(15) yes C30 . H301 . 0.976 no C30 . H302 . 0.981 no O31 . C32 . 1.387(10) yes C32 . C33 . 1.340(12) yes C32 . C37 . 1.381(11) yes C33 . C34 . 1.346(12) yes C33 . H331 . 0.921 no C34 . C35 . 1.400(10) yes C34 . H341 . 0.924 no C35 . C36 . 1.383(10) yes C35 . O38 . 1.357(8) yes C36 . C37 . 1.375(11) yes C36 . H361 . 0.921 no C37 . H371 . 0.940 no O38 . C39 . 1.416(8) yes C39 . C40 . 1.532(10) yes C39 . H391 . 0.961 no C39 . H392 . 0.968 no C40 . N41 . 1.453(9) yes C40 . H401 . 0.953 no C40 . H402 . 0.968 no N41 . C42 . 1.332(9) yes N41 . H411 . 0.850 no C42 . O43 . 1.246(8) yes S101 . O103 5_565 1.486(6) yes S101 . O103 3_665 1.486(6) yes S101 . O102 . 1.395(12) yes S101 . O103 . 1.486(6) yes S104 . O110 3_665 1.57000(9) yes S104 . O110 5_565 1.57000(9) yes S104 . O108 3_665 1.49000(9) yes S104 . O108 5_565 1.49000(9) yes S104 . O109 5_565 1.49000(9) yes S104 . O109 3_665 1.49000(9) yes S104 . O107 3_665 1.49000(9) yes S104 . O107 5_565 1.49000(9) yes S104 . O107 . 1.49000(9) yes S104 . O108 . 1.49000(9) yes S104 . O109 . 1.49000(9) yes S104 . O110 . 1.57000(9) yes O107 . H1071 . 0.903 no O111 . H1111 . 0.850 no O201 . H2011 . 0.850 no O201 . H2012 . 0.850 no O201 . H2013 . 0.850 no O202 . H2021 3_555 0.850 no O202 . H2021 5_555 0.850 no O202 . H2021 . 0.850 no O202 . H2022 . 0.850 no O203 . H2032 . 0.822 no O203 . H2033 . 0.850 no O203 . H2031 . 0.850 no O204 . H241 3_555 0.850 no O204 . H241 5_555 0.850 no O204 . H241 . 0.850 no O204 . H242 . 0.850 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 N2 . C1 . H11 . 110.5 no N2 . C1 . H12 . 109.3 no H11 . C1 . H12 . 109.7 no N2 . C1 . H13 . 108.2 no H11 . C1 . H13 . 109.5 no H12 . C1 . H13 . 109.6 no C1 . N2 . C3 . 121.1(6) yes C1 . N2 . C7 . 117.7(6) yes C3 . N2 . C7 . 121.2(7) yes N2 . C3 . C4 . 122.5(7) yes N2 . C3 . H31 . 119.0 no C4 . C3 . H31 . 118.6 no C3 . C4 . C5 . 117.8(7) yes C3 . C4 . C8 . 118.5(6) yes C5 . C4 . C8 . 123.7(7) yes C4 . C5 . C6 . 118.5(7) yes C4 . C5 . H51 . 122.0 no C6 . C5 . H51 . 119.5 no C5 . C6 . C7 . 120.3(6) yes C5 . C6 . C42 . 118.1(6) yes C7 . C6 . C42 . 121.6(7) yes C6 . C7 . N2 . 119.7(7) yes C6 . C7 . H71 . 118.4 no N2 . C7 . H71 . 121.9 no C4 . C8 . O9 . 118.5(8) yes C4 . C8 . N10 . 117.6(6) yes O9 . C8 . N10 . 123.9(7) yes C8 . N10 . C11 . 123.8(6) yes C8 . N10 . H101 . 118.0 no C11 . N10 . H101 . 118.2 no N10 . C11 . C12 . 109.5(6) yes N10 . C11 . H111 . 110.8 no C12 . C11 . H111 . 111.3 no N10 . C11 . H112 . 108.2 no C12 . C11 . H112 . 108.6 no H111 . C11 . H112 . 108.4 no C11 . C12 . O13 . 108.1(7) yes C11 . C12 . H121 . 110.0 no O13 . C12 . H121 . 110.7 no C11 . C12 . H122 . 109.0 no O13 . C12 . H122 . 109.8 no H121 . C12 . H122 . 109.2 no C12 . O13 . C14 . 118.1(6) yes O13 . C14 . C15 . 115.4(8) yes O13 . C14 . C19 . 125.5(7) yes C15 . C14 . C19 . 119.1(8) yes C14 . C15 . C16 . 120.1(9) yes C14 . C15 . H151 . 119.0 no C16 . C15 . H151 . 120.9 no C15 . C16 . C17 . 120.5(8) yes C15 . C16 . H161 . 119.7 no C17 . C16 . H161 . 119.8 no C16 . C17 . C18 . 118.8(8) yes C16 . C17 . O20 . 125.5(8) yes C18 . C17 . O20 . 115.7(8) yes C17 . C18 . C19 . 120.8(8) yes C17 . C18 . H181 . 118.0 no C19 . C18 . H181 . 121.2 no C14 . C19 . C18 . 120.6(7) yes C14 . C19 . H191 . 118.7 no C18 . C19 . H191 . 120.6 no C17 . O20 . C21 . 118.4(8) yes O20 . C21 . C22 . 108.1(10) yes O20 . C21 . H211 . 110.7 no C22 . C21 . H211 . 109.6 no O20 . C21 . H212 . 109.4 no C22 . C21 . H212 . 109.4 no H211 . C21 . H212 . 109.7 no C21 . C22 . O23 . 108.0(9) yes C21 . C22 . H221 . 110.3 no O23 . C22 . H221 . 107.7 no C21 . C22 . H222 . 111.5 no O23 . C22 . H222 . 110.2 no H221 . C22 . H222 . 109.1 no C22 . O23 . C24 . 110.5(9) yes O23 . C24 . C25 . 111.8(10) yes O23 . C24 . H2041 . 105.9 no C25 . C24 . H2041 . 109.8 no O23 . C24 . H2042 . 110.9 no C25 . C24 . H2042 . 107.4 no H2041 . C24 . H2042 . 111.1 no C24 . C25 . C26 . 122.5(12) yes C24 . C25 . H251 . 120.6 no C26 . C25 . H251 . 116.9 no C25 . C26 . C27 . 125.8(12) yes C25 . C26 . H261 . 116.6 no C27 . C26 . H261 . 117.6 no C26 . C27 . O28 . 110.5(9) yes C26 . C27 . H271 . 108.7 no O28 . C27 . H271 . 111.1 no C26 . C27 . H272 . 107.7 no O28 . C27 . H272 . 109.2 no H271 . C27 . H272 . 109.6 no C27 . O28 . C29 . 113.2(11) yes O28 . C29 . C30 . 107.4(12) yes O28 . C29 . H291 . 107.1 no C30 . C29 . H291 . 110.2 no O28 . C29 . H292 . 111.2 no C30 . C29 . H292 . 111.4 no H291 . C29 . H292 . 109.5 no C29 . C30 . O31 . 109.0(11) yes C29 . C30 . H301 . 111.3 no O31 . C30 . H301 . 108.6 no C29 . C30 . H302 . 108.7 no O31 . C30 . H302 . 109.2 no H301 . C30 . H302 . 110.0 no C30 . O31 . C32 . 118.5(9) yes O31 . C32 . C33 . 123.0(7) yes O31 . C32 . C37 . 117.6(7) yes C33 . C32 . C37 . 119.2(7) yes C32 . C33 . C34 . 122.6(8) yes C32 . C33 . H331 . 119.2 no C34 . C33 . H331 . 118.1 no C33 . C34 . C35 . 120.1(8) yes C33 . C34 . H341 . 121.1 no C35 . C34 . H341 . 118.8 no C34 . C35 . C36 . 117.1(7) yes C34 . C35 . O38 . 126.4(7) yes C36 . C35 . O38 . 116.4(6) yes C35 . C36 . C37 . 121.5(7) yes C35 . C36 . H361 . 119.3 no C37 . C36 . H361 . 119.2 no C32 . C37 . C36 . 119.2(7) yes C32 . C37 . H371 . 120.4 no C36 . C37 . H371 . 120.3 no C35 . O38 . C39 . 118.4(5) yes O38 . C39 . C40 . 113.4(6) yes O38 . C39 . H391 . 107.7 no C40 . C39 . H391 . 108.4 no O38 . C39 . H392 . 108.6 no C40 . C39 . H392 . 110.2 no H391 . C39 . H392 . 108.5 no C39 . C40 . N41 . 110.9(6) yes C39 . C40 . H401 . 109.5 no N41 . C40 . H401 . 108.5 no C39 . C40 . H402 . 109.7 no N41 . C40 . H402 . 107.9 no H401 . C40 . H402 . 110.2 no C40 . N41 . C42 . 123.1(6) yes C40 . N41 . H411 . 119.4 no C42 . N41 . H411 . 117.5 no C6 . C42 . N41 . 115.8(6) yes C6 . C42 . O43 . 120.3(6) yes N41 . C42 . O43 . 123.8(6) yes O103 5_565 S101 . O103 3_665 107.2(3) yes O103 5_565 S101 . O102 . 111.6(2) yes O103 3_665 S101 . O102 . 111.6(2) yes O103 5_565 S101 . O103 . 107.2(3) yes O103 3_665 S101 . O103 . 107.2(3) yes O102 . S101 . O103 . 111.6(2) yes O110 3_665 S104 . O108 3_665 108.44(5) yes O110 5_565 S104 . O108 5_565 108.44(5) yes O108 3_665 S104 . O108 5_565 113.0(12) yes O110 5_565 S104 . O109 5_565 108.44(5) yes O108 5_565 S104 . O109 5_565 110.48(5) yes O110 3_665 S104 . O109 3_665 108.44(5) yes O108 3_665 S104 . O109 3_665 110.48(5) yes O108 5_565 S104 . O109 3_665 119(3) yes O110 3_665 S104 . O107 3_665 108.45(5) yes O110 5_565 S104 . O107 3_665 111.2(19) yes O108 3_665 S104 . O107 3_665 110.48(5) yes O110 5_565 S104 . O107 5_565 108.45(5) yes O108 3_665 S104 . O107 5_565 123.4(5) yes O108 5_565 S104 . O107 5_565 110.48(5) yes O109 5_565 S104 . O107 5_565 110.49(5) yes O110 3_665 S104 . O107 . 111.2(19) yes O108 5_565 S104 . O107 . 123.4(5) yes O108 3_665 S104 . O108 . 113.0(12) yes O108 5_565 S104 . O108 . 113.0(12) yes O109 5_565 S104 . O108 . 119(3) yes O110 3_665 S104 . O109 . 127(2) yes O108 3_665 S104 . O109 . 119(3) yes O109 5_565 S104 . O110 . 127(2) yes O109 3_665 S104 . O107 3_665 110.49(5) yes O107 3_665 S104 . O107 5_565 119.1(4) yes O107 3_665 S104 . O107 . 119.1(4) yes O107 5_565 S104 . O107 . 119.1(4) yes O107 3_665 S104 . O108 . 123.4(5) yes O107 . S104 . O108 . 110.48(5) yes O107 . S104 . O109 . 110.49(5) yes O108 . S104 . O109 . 110.48(5) yes O109 3_665 S104 . O110 . 141.7(17) yes O107 5_565 S104 . O110 . 111.2(19) yes O107 . S104 . O110 . 108.45(5) yes O108 . S104 . O110 . 108.44(5) yes O109 . S104 . O110 . 108.44(5) yes S104 . O107 . H1071 . 110.4 no S104 . O111 . H1111 . 109.4 no H2011 . O201 . H2012 . 113.0 no H2011 . O201 . H2013 . 124.8 no H2012 . O201 . H2013 . 115.4 no H2021 3_555 O202 . H2021 5_555 101.9 no H2021 3_555 O202 . H2021 . 101.9 no H2021 5_555 O202 . H2021 . 101.9 no H2021 3_555 O202 . H2022 . 116.3 no H2021 5_555 O202 . H2022 . 116.3 no H2021 . O202 . H2022 . 116.3 no H2032 . O203 . H2033 . 112.2 no H2033 . O203 . H2031 . 120.5 no H241 3_555 O204 . H241 5_555 106.8 no H241 3_555 O204 . H241 . 106.8 no H241 5_555 O204 . H241 . 106.8 no H241 3_555 O204 . H242 . 112.0 no H241 5_555 O204 . H242 . 112.0 no H241 . O204 . H242 . 112.0 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 C1 . H11 . O102 . 166 0.95 2.53 3.461(14) yes C5 . H51 . O43 12_555 150 0.94 2.24 3.091(14) yes C7 . H71 . O103 5_565 171 0.94 2.22 3.153(14) yes C16 . H161 . O201 12_555 147 0.93 2.57 3.390(14) yes C24 . H2042 . O9 9_554 146 0.98 2.45 3.307(14) yes C27 . H271 . O107 4_555 173 0.97 2.46 3.427(14) yes C37 . H371 . O103 12_555 151 0.94 2.42 3.269(14) yes C39 . H392 . O110 . 143 0.97 2.40 3.221(14) yes C40 . H401 . O105 . 129 0.95 2.51 3.195(14) yes C29 . H291 . O106 6_655 147 0.95 2.43 3.267(14) yes C29 . H291 . O111 2_665 147 0.95 2.39 3.231(14) yes C29 . H291 . O112 4_555 146 0.95 2.41 3.243(14) yes N10 . H101 . O43 12_555 162 0.85 2.06 2.884(14) yes N41 . H411 . O103 . 155 0.85 1.96 2.757(14) yes O201 . H2011 . O13 . 178 0.85 2.02 2.865(14) yes O201 . H2012 . O203 . 178 0.85 2.04 2.893(14) yes O202 . H2021 . O201 . 174 0.85 1.90 2.744(14) yes O204 . H241 . O203 . 174 0.85 1.73 2.573(14) yes O204 . H242 . O204 2_556 180 0.85 2.10 2.951(14) yes O202 . H2022 . O202 8_555 180 0.85 1.87 2.716(14) yes O201 . H2013 . O202 . 173 0.85 1.90 2.744(14) yes O203 . H2032 . O201 . 163 0.82 2.10 2.893(14) yes O203 . H2033 . O204 . 174 0.85 1.73 2.573(14) yes O203 . H2031 . O9 . 133 0.85 2.07 2.727(14) yes