# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address 'Christopher J. Serpell' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA. UK. ; 'Owen Thomas' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; 'Barbara Odell' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; 'Timothy D. W. Claridge' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; 'Ricky Chall' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; ; A.Thompson ; ; 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 'Christopher J. Serpell' _publ_contact_author_address ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; _publ_contact_author_email christopher.serpell@chem.ox.ac.uk _publ_section_title ; Dimeric Self-Association of an Isophthalamide Macrocycle in Solution and the Solid State ; _publ_section_abstract ; An isophthalamide macrocycle used in anion-templated interpenetrated structures is found to participate in dimeric self-assembly throughout eight different crystal forms. Analysis of these, in combination with solution-phase NMR studies, reveals the nature of the hydrogen-bonded self-association, yielding new perspectives and potential applications for the macrocycle system. ; # Attachment '- crystallographicdata.cif' #============================================================================== #TrackingRef '- crystallographicdata.cif' #============================================================================== #============================================================================== data_SynSynPolymorph _database_code_depnum_ccdc_archive 'CCDC 815167' #TrackingRef '- crystallographicdata.cif' #============================================================================== _audit_creation_date 11-01-12 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 041CJS09 _chemical_name_systematic . _chemical_melting_point . # start Validation Reply Form _vrf_REFLT03_SynSynPolymorph ; PROBLEM: Reflection count < 85% complete (theta max?) RESPONSE: The reflections dropped off very rapidly at higher angle. A data collection strategy was employed that, while obtaining data well beyond the limit of visual inspection, did not extend to the full 27.5 degrees. This was deemed reasonable since there were no data to be collected at this angle. ; _vrf_PLAT022_SynSynPolymorph ; PROBLEM: Ratio Unique / Expected Reflections too Low .... 0.80 RESPONSE: The reflections dropped off very rapidly at higher angle. A data collection strategy was employed that, while obtaining data well beyond the limit of visual inspection, did not extend to the full 27.5 degrees. This was deemed reasonable since there were no data to be collected at this angle. ; _vrf_PLAT029_SynSynPolymorph ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.80 RESPONSE: The reflections dropped off very rapidly at higher angle. A data collection strategy was employed that, while obtaining data well beyond the limit of visual inspection, did not extend to the full 27.5 degrees. This was deemed reasonable since there were no data to be collected at this angle. ; # end Validation Reply Form _cell_length_a 8.8825(19) _cell_length_b 9.736(2) _cell_length_c 19.949(5) _cell_angle_alpha 86.367(12) _cell_angle_beta 82.052(10) _cell_angle_gamma 74.500(8) _cell_volume 1646.0(7) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol 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' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C28 N8 O15 # Dc = 1.39 Fooo = 696.00 Mu = 1.17 M = 688.35 # Found Formula = C36 H46 N2 O9 # Dc = 1.31 FOOO = 696.00 Mu = 0.94 M = 650.77 _chemical_formula_sum 'C36 H46 N2 O9' _chemical_formula_moiety 'C36 H46 N2 O9' _chemical_compound_source ? _chemical_formula_weight 650.77 _cell_measurement_reflns_used 3381 _cell_measurement_theta_min 5 _cell_measurement_theta_max 25 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.080 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_max 0.400 _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.094 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 12017 _reflns_number_total 4891 _diffrn_reflns_av_R_equivalents 0.145 # Number of reflections without Friedels Law is 7141 # Number of reflections with Friedels Law is 4891 # Theoretical number of reflections is about 3556 _diffrn_reflns_theta_min 5.116 _diffrn_reflns_theta_max 25.441 _diffrn_measured_fraction_theta_max 0.802 _diffrn_reflns_theta_full 25.441 _diffrn_measured_fraction_theta_full 0.802 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -8 _reflns_limit_h_max 10 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 1.66 _oxford_diffrn_Wilson_scale 8.32 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.57 _refine_diff_density_max 0.55 # 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 3014 _refine_ls_number_restraints 0 _refine_ls_number_parameters 424 _oxford_refine_ls_R_factor_ref 0.1579 _refine_ls_wR_factor_ref 0.2470 _refine_ls_goodness_of_fit_ref 1.0927 _refine_ls_shift/su_max 0.0001382 _refine_ls_shift/su_mean 0.0000285 # The values computed from all data _oxford_reflns_number_all 3014 _refine_ls_R_factor_all 0.1579 _refine_ls_wR_factor_all 0.2470 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2242 _refine_ls_R_factor_gt 0.1236 _refine_ls_wR_factor_gt 0.2289 # 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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.01P)^2^ +13.29P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. 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 0.0807(13) 0.6483(11) 0.6679(5) 0.0448 1.0000 Uani . . . . . . . C2 C 0.0595(13) 0.7571(12) 0.6195(5) 0.0499 1.0000 Uani . . . . . . . C3 C 0.1836(13) 0.7773(11) 0.5738(5) 0.0449 1.0000 Uani . . . . . . . C4 C 0.3408(13) 0.6938(11) 0.5772(5) 0.0449 1.0000 Uani . . . . . . . C5 C 0.3571(13) 0.5874(11) 0.6290(5) 0.0487 1.0000 Uani . . . . . . . C6 C 0.2341(14) 0.5632(10) 0.6737(5) 0.0441 1.0000 Uani . . . . . . . C7 C 0.4735(12) 0.7342(11) 0.5343(5) 0.0450 1.0000 Uani . . . . . . . C8 C 0.5032(15) 0.8594(12) 0.5657(6) 0.0602 1.0000 Uani . . . . . . . C9 C 0.4411(13) 0.7730(11) 0.4617(5) 0.0500 1.0000 Uani . . . . . . . C10 C 0.6300(13) 0.6107(11) 0.5311(5) 0.0556 1.0000 Uani . . . . . . . C11 C 0.2702(15) 0.4525(11) 0.7298(5) 0.0477 1.0000 Uani . . . . . . . O12 O 0.4077(10) 0.3906(9) 0.7363(4) 0.0748 1.0000 Uani . . . . . . . N13 N 0.1524(11) 0.4290(9) 0.7727(4) 0.0465 1.0000 Uani . . . . . . . C14 C 0.1717(14) 0.3336(12) 0.8303(5) 0.0538 1.0000 Uani . . . . . . . C15 C 0.2054(14) 0.3988(12) 0.8892(5) 0.0509 1.0000 Uani . . . . . . . O16 O 0.2052(9) 0.3047(7) 0.9447(3) 0.0502 1.0000 Uani . . . . . . . C17 C 0.2058(11) 0.3446(11) 1.0084(5) 0.0397 1.0000 Uani . . . . . . . C18 C 0.2454(12) 0.4715(12) 1.0211(6) 0.0508 1.0000 Uani . . . . . . . C19 C 0.2460(12) 0.5089(11) 1.0874(5) 0.0466 1.0000 Uani . . . . . . . C20 C 0.2126(12) 0.4228(11) 1.1394(5) 0.0398 1.0000 Uani . . . . . . . C21 C 0.1749(12) 0.2936(11) 1.1271(5) 0.0465 1.0000 Uani . . . . . . . C22 C 0.1752(11) 0.2639(11) 1.0622(5) 0.0412 1.0000 Uani . . . . . . . O23 O 0.2040(8) 0.4491(7) 1.2072(3) 0.0475 1.0000 Uani . . . . . . . C24 C 0.2708(12) 0.5612(12) 1.2222(5) 0.0485 1.0000 Uani . . . . . . . C25 C 0.2443(12) 0.5785(12) 1.2970(5) 0.0516 1.0000 Uani . . . . . . . O26 O 0.0801(8) 0.6496(8) 1.3160(3) 0.0574 1.0000 Uani . . . . . . . C27 C 0.0486(12) 0.6943(11) 1.3837(5) 0.0449 1.0000 Uani . . . . . . . C28 C -0.1155(14) 0.7927(11) 1.3947(5) 0.0596 1.0000 Uani . . . . . . . O29 O -0.1299(9) 0.9235(8) 1.3554(3) 0.0600 1.0000 Uani . . . . . . . C30 C -0.1794(14) 0.9188(11) 1.2916(5) 0.0523 1.0000 Uani . . . . . . . C31 C -0.2219(13) 1.0685(11) 1.2637(5) 0.0484 1.0000 Uani . . . . . . . O32 O -0.2762(9) 1.0671(8) 1.2004(3) 0.0580 1.0000 Uani . . . . . . . C33 C -0.3395(14) 1.2061(11) 1.1741(5) 0.0534 1.0000 Uani . . . . . . . C34 C -0.3776(13) 1.1995(12) 1.1047(5) 0.0528 1.0000 Uani . . . . . . . O35 O -0.2385(9) 1.1679(8) 1.0583(3) 0.0568 1.0000 Uani . . . . . . . C36 C -0.2489(14) 1.1447(11) 0.9919(5) 0.0446 1.0000 Uani . . . . . . . C37 C -0.1105(13) 1.1138(10) 0.9483(5) 0.0435 1.0000 Uani . . . . . . . C38 C -0.1081(14) 1.0879(9) 0.8813(5) 0.0463 1.0000 Uani . . . . . . . C39 C -0.2464(14) 1.0875(11) 0.8568(5) 0.0431 1.0000 Uani . . . . . . . C40 C -0.3862(12) 1.1184(11) 0.8985(5) 0.0422 1.0000 Uani . . . . . . . C41 C -0.3885(13) 1.1457(10) 0.9668(6) 0.0473 1.0000 Uani . . . . . . . O42 O -0.2295(9) 1.0596(8) 0.7893(3) 0.0518 1.0000 Uani . . . . . . . C43 C -0.3656(13) 1.0499(11) 0.7610(5) 0.0508 1.0000 Uani . . . . . . . C44 C -0.3140(12) 1.0241(11) 0.6870(5) 0.0450 1.0000 Uani . . . . . . . N45 N -0.1826(9) 0.8957(9) 0.6779(4) 0.0447 1.0000 Uani . . . . . . . C46 C -0.0976(13) 0.8678(11) 0.6165(5) 0.0442 1.0000 Uani . . . . . . . O47 O -0.1359(9) 0.9263(8) 0.5647(4) 0.0547 1.0000 Uani . . . . . . . H11 H -0.0052 0.6313 0.6962 0.0539 1.0000 Uiso R . . . . . . H31 H 0.1646 0.8476 0.5400 0.0539 1.0000 Uiso R . . . . . . H51 H 0.4572 0.5296 0.6332 0.0590 1.0000 Uiso R . . . . . . H82 H 0.5829 0.8933 0.5369 0.0898 1.0000 Uiso R . . . . . . H81 H 0.5375 0.8304 0.6093 0.0900 1.0000 Uiso R . . . . . . H83 H 0.4063 0.9347 0.5715 0.0900 1.0000 Uiso R . . . . . . H93 H 0.5332 0.7905 0.4350 0.0751 1.0000 Uiso R . . . . . . H91 H 0.3555 0.8580 0.4607 0.0750 1.0000 Uiso R . . . . . . H92 H 0.4141 0.6959 0.4428 0.0752 1.0000 Uiso R . . . . . . H101 H 0.7111 0.6408 0.5016 0.0830 1.0000 Uiso R . . . . . . H102 H 0.6609 0.5900 0.5760 0.0828 1.0000 Uiso R . . . . . . H103 H 0.6120 0.5268 0.5136 0.0829 1.0000 Uiso R . . . . . . H142 H 0.0756 0.3043 0.8431 0.0648 1.0000 Uiso R . . . . . . H141 H 0.2583 0.2505 0.8181 0.0649 1.0000 Uiso R . . . . . . H152 H 0.1241 0.4859 0.8995 0.0599 1.0000 Uiso R . . . . . . H151 H 0.3059 0.4203 0.8792 0.0600 1.0000 Uiso R . . . . . . H181 H 0.2719 0.5299 0.9852 0.0609 1.0000 Uiso R . . . . . . H191 H 0.2693 0.5933 1.0957 0.0551 1.0000 Uiso R . . . . . . H211 H 0.1517 0.2330 1.1626 0.0558 1.0000 Uiso R . . . . . . H221 H 0.1521 0.1796 1.0539 0.0499 1.0000 Uiso R . . . . . . H241 H 0.3834 0.5376 1.2066 0.0580 1.0000 Uiso R . . . . . . H242 H 0.2194 0.6493 1.1996 0.0580 1.0000 Uiso R . . . . . . H251 H 0.3103 0.6363 1.3093 0.0617 1.0000 Uiso R . . . . . . H252 H 0.2704 0.4859 1.3201 0.0618 1.0000 Uiso R . . . . . . H271 H 0.1248 0.7435 1.3924 0.0541 1.0000 Uiso R . . . . . . H272 H 0.0539 0.6123 1.4147 0.0539 1.0000 Uiso R . . . . . . H281 H -0.1410 0.8150 1.4424 0.0710 1.0000 Uiso R . . . . . . H282 H -0.1900 0.7446 1.3825 0.0711 1.0000 Uiso R . . . . . . H302 H -0.2700 0.8796 1.2965 0.0631 1.0000 Uiso R . . . . . . H301 H -0.0944 0.8600 1.2616 0.0630 1.0000 Uiso R . . . . . . H312 H -0.3028 1.1282 1.2951 0.0580 1.0000 Uiso R . . . . . . H311 H -0.1290 1.1049 1.2570 0.0580 1.0000 Uiso R . . . . . . H331 H -0.4327 1.2535 1.2035 0.0640 1.0000 Uiso R . . . . . . H332 H -0.2608 1.2594 1.1715 0.0640 1.0000 Uiso R . . . . . . H342 H -0.4443 1.2909 1.0921 0.0630 1.0000 Uiso R . . . . . . H341 H -0.4331 1.1256 1.1037 0.0630 1.0000 Uiso R . . . . . . H371 H -0.0165 1.1097 0.9651 0.0521 1.0000 Uiso R . . . . . . H381 H -0.0138 1.0710 0.8523 0.0551 1.0000 Uiso R . . . . . . H401 H -0.4796 1.1216 0.8819 0.0510 1.0000 Uiso R . . . . . . H411 H -0.4830 1.1644 0.9955 0.0570 1.0000 Uiso R . . . . . . H431 H -0.4493 1.1381 0.7666 0.0610 1.0000 Uiso R . . . . . . H432 H -0.4028 0.9709 0.7830 0.0610 1.0000 Uiso R . . . . . . H441 H -0.2813 1.1053 0.6651 0.0530 1.0000 Uiso R . . . . . . H442 H -0.4011 1.0107 0.6663 0.0528 1.0000 Uiso R . . . . . . H131 H 0.0589 0.4658 0.7633 0.0560 1.0000 Uiso R . . . . . . H451 H -0.1460 0.8518 0.7133 0.0540 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 C1 0.041(8) 0.039(7) 0.055(7) -0.011(6) -0.002(5) -0.011(6) C2 0.042(8) 0.057(8) 0.044(6) 0.015(6) -0.006(6) -0.007(6) C3 0.044(8) 0.044(7) 0.045(6) -0.003(5) -0.018(6) -0.001(6) C4 0.057(9) 0.042(7) 0.037(6) -0.003(5) -0.002(5) -0.016(6) C5 0.038(8) 0.040(7) 0.060(7) -0.006(6) -0.014(6) 0.008(6) C6 0.054(8) 0.027(6) 0.050(6) -0.001(5) -0.001(6) -0.011(6) C7 0.032(7) 0.039(7) 0.060(7) 0.015(5) -0.002(5) -0.007(5) C8 0.072(9) 0.037(7) 0.085(8) 0.000(6) -0.012(7) -0.037(6) C9 0.045(8) 0.038(6) 0.065(7) 0.007(5) -0.005(6) -0.010(5) C10 0.048(8) 0.047(7) 0.069(7) 0.010(6) -0.006(6) -0.012(6) C11 0.050(9) 0.034(7) 0.057(7) 0.002(5) -0.010(7) -0.006(6) O12 0.042(6) 0.076(6) 0.088(6) 0.029(5) -0.011(4) 0.010(5) N13 0.032(6) 0.049(6) 0.058(6) 0.006(4) -0.004(5) -0.012(4) C14 0.049(8) 0.069(8) 0.041(6) 0.013(6) -0.005(5) -0.015(6) C15 0.051(8) 0.054(7) 0.042(6) -0.002(6) 0.002(5) -0.009(6) O16 0.061(6) 0.040(4) 0.046(5) -0.001(4) -0.009(4) -0.005(4) C17 0.012(6) 0.051(7) 0.054(7) 0.007(6) -0.005(5) -0.006(5) C18 0.037(7) 0.046(8) 0.063(8) 0.011(6) 0.000(5) -0.005(6) C19 0.050(8) 0.031(6) 0.054(7) -0.005(6) -0.001(5) -0.005(5) C20 0.030(7) 0.048(7) 0.041(6) 0.004(5) 0.004(5) -0.014(5) C21 0.050(8) 0.029(6) 0.053(7) 0.001(5) -0.002(5) 0.001(5) C22 0.029(7) 0.036(6) 0.059(8) 0.003(6) -0.002(5) -0.012(5) O23 0.047(5) 0.043(5) 0.058(5) -0.002(3) -0.006(4) -0.022(4) C24 0.031(7) 0.054(7) 0.063(7) 0.012(6) -0.008(5) -0.017(6) C25 0.037(8) 0.051(7) 0.068(8) 0.005(6) -0.015(6) -0.011(6) O26 0.038(5) 0.064(5) 0.061(5) -0.012(4) -0.012(4) 0.006(4) C27 0.037(7) 0.045(7) 0.050(7) 0.006(5) -0.006(5) -0.008(5) C28 0.084(10) 0.031(7) 0.051(6) -0.002(5) -0.011(6) 0.008(6) O29 0.072(6) 0.046(5) 0.059(5) 0.001(4) -0.018(4) -0.005(4) C30 0.065(9) 0.037(7) 0.058(7) -0.004(5) -0.011(6) -0.017(6) C31 0.053(8) 0.041(7) 0.046(6) -0.002(5) -0.005(5) -0.002(5) O32 0.068(6) 0.043(5) 0.053(5) -0.001(4) -0.016(4) 0.006(4) C33 0.057(8) 0.051(8) 0.044(6) -0.001(5) -0.004(6) -0.001(6) C34 0.039(8) 0.040(7) 0.072(8) -0.011(6) 0.002(6) -0.001(5) O35 0.047(5) 0.058(5) 0.057(5) -0.002(4) -0.007(4) 0.001(4) C36 0.044(8) 0.039(7) 0.045(7) 0.001(5) -0.009(6) 0.001(5) C37 0.042(8) 0.041(7) 0.047(7) 0.000(5) -0.012(6) -0.007(5) C38 0.054(9) 0.014(5) 0.060(8) 0.000(5) -0.002(6) 0.006(5) C39 0.045(8) 0.041(7) 0.045(7) 0.002(5) -0.007(6) -0.012(5) C40 0.024(7) 0.052(7) 0.047(7) 0.003(5) -0.008(5) -0.004(5) C41 0.036(8) 0.024(6) 0.073(8) 0.007(5) 0.002(6) 0.001(5) O42 0.043(5) 0.053(5) 0.056(5) -0.007(4) -0.008(4) -0.003(4) C43 0.040(8) 0.040(7) 0.067(7) -0.011(5) -0.017(6) 0.006(5) C44 0.023(6) 0.051(7) 0.064(7) 0.002(5) -0.014(5) -0.012(5) N45 0.033(6) 0.044(6) 0.052(6) 0.004(4) -0.009(4) 0.001(4) C46 0.052(8) 0.043(7) 0.042(7) 0.005(6) -0.014(6) -0.017(6) O47 0.048(5) 0.050(5) 0.058(5) 0.003(4) -0.013(4) 0.003(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.508(2) 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 . C2 . 1.380(13) yes C1 . C6 . 1.408(14) yes C1 . H11 . 0.930 no C2 . C3 . 1.379(15) yes C2 . C46 . 1.525(14) yes C3 . C4 . 1.424(14) yes C3 . H31 . 0.929 no C4 . C5 . 1.409(14) yes C4 . C7 . 1.484(15) yes C5 . C6 . 1.373(15) yes C5 . H51 . 0.928 no C6 . C11 . 1.509(14) yes C7 . C8 . 1.505(15) yes C7 . C9 . 1.520(13) yes C7 . C10 . 1.573(13) yes C8 . H82 . 0.963 no C8 . H81 . 0.963 no C8 . H83 . 0.968 no C9 . H93 . 0.961 no C9 . H91 . 0.964 no C9 . H92 . 0.960 no C10 . H101 . 0.962 no C10 . H102 . 0.966 no C10 . H103 . 0.968 no C11 . O12 . 1.230(13) yes C11 . N13 . 1.318(13) yes N13 . C14 . 1.430(12) yes N13 . H131 . 0.854 no C14 . C15 . 1.472(15) yes C14 . H142 . 0.968 no C14 . H141 . 0.973 no C15 . O16 . 1.392(11) yes C15 . H152 . 0.968 no C15 . H151 . 0.963 no O16 . C17 . 1.352(12) yes C17 . C18 . 1.418(15) yes C17 . C22 . 1.331(13) yes C18 . C19 . 1.397(15) yes C18 . H181 . 0.930 no C19 . C20 . 1.343(13) yes C19 . H191 . 0.929 no C20 . C21 . 1.429(15) yes C20 . O23 . 1.379(12) yes C21 . C22 . 1.345(14) yes C21 . H211 . 0.929 no C22 . H221 . 0.927 no O23 . C24 . 1.438(13) yes C24 . C25 . 1.492(14) yes C24 . H241 . 0.975 no C24 . H242 . 0.971 no C25 . O26 . 1.446(12) yes C25 . H251 . 0.976 no C25 . H252 . 0.971 no O26 . C27 . 1.413(11) yes C27 . C28 . 1.511(14) yes C27 . H271 . 0.967 no C27 . H272 . 0.973 no C28 . O29 . 1.438(12) yes C28 . H281 . 0.971 no C28 . H282 . 0.970 no O29 . C30 . 1.410(12) yes C30 . C31 . 1.496(13) yes C30 . H302 . 0.970 no C30 . H301 . 0.972 no C31 . O32 . 1.415(12) yes C31 . H312 . 0.973 no C31 . H311 . 0.972 no O32 . C33 . 1.417(12) yes C33 . C34 . 1.479(14) yes C33 . H331 . 0.969 no C33 . H332 . 0.970 no C34 . O35 . 1.413(12) yes C34 . H342 . 0.968 no C34 . H341 . 0.977 no O35 . C36 . 1.376(12) yes C36 . C37 . 1.378(14) yes C36 . C41 . 1.398(15) yes C37 . C38 . 1.371(14) yes C37 . H371 . 0.931 no C38 . C39 . 1.385(15) yes C38 . H381 . 0.932 no C39 . C40 . 1.367(14) yes C39 . O42 . 1.371(12) yes C40 . C41 . 1.402(14) yes C40 . H401 . 0.926 no C41 . H411 . 0.929 no O42 . C43 . 1.430(12) yes C43 . C44 . 1.501(13) yes C43 . H431 . 0.974 no C43 . H432 . 0.973 no C44 . N45 . 1.466(12) yes C44 . H441 . 0.971 no C44 . H442 . 0.967 no N45 . C46 . 1.349(12) yes N45 . H451 . 0.859 no C46 . O47 . 1.195(11) 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 C2 . C1 . C6 . 119.0(10) yes C2 . C1 . H11 . 120.4 no C6 . C1 . H11 . 120.6 no C1 . C2 . C3 . 121.3(10) yes C1 . C2 . C46 . 122.5(10) yes C3 . C2 . C46 . 116.0(9) yes C2 . C3 . C4 . 121.7(9) yes C2 . C3 . H31 . 119.3 no C4 . C3 . H31 . 119.0 no C3 . C4 . C5 . 114.8(10) yes C3 . C4 . C7 . 119.8(9) yes C5 . C4 . C7 . 125.0(10) yes C4 . C5 . C6 . 124.2(10) yes C4 . C5 . H51 . 118.2 no C6 . C5 . H51 . 117.6 no C1 . C6 . C5 . 118.9(9) yes C1 . C6 . C11 . 122.5(10) yes C5 . C6 . C11 . 118.5(10) yes C4 . C7 . C8 . 107.9(9) yes C4 . C7 . C9 . 113.0(10) yes C8 . C7 . C9 . 109.5(8) yes C4 . C7 . C10 . 112.0(8) yes C8 . C7 . C10 . 107.3(10) yes C9 . C7 . C10 . 107.0(8) yes C7 . C8 . H82 . 109.9 no C7 . C8 . H81 . 109.1 no H82 . C8 . H81 . 109.8 no C7 . C8 . H83 . 109.2 no H82 . C8 . H83 . 109.9 no H81 . C8 . H83 . 109.0 no C7 . C9 . H93 . 110.0 no C7 . C9 . H91 . 109.8 no H93 . C9 . H91 . 108.8 no C7 . C9 . H92 . 109.6 no H93 . C9 . H92 . 109.1 no H91 . C9 . H92 . 109.6 no C7 . C10 . H101 . 108.8 no C7 . C10 . H102 . 109.5 no H101 . C10 . H102 . 109.8 no C7 . C10 . H103 . 108.9 no H101 . C10 . H103 . 109.8 no H102 . C10 . H103 . 110.0 no C6 . C11 . O12 . 120.0(11) yes C6 . C11 . N13 . 118.6(10) yes O12 . C11 . N13 . 121.3(9) yes C11 . N13 . C14 . 124.0(9) yes C11 . N13 . H131 . 118.0 no C14 . N13 . H131 . 117.7 no N13 . C14 . C15 . 112.9(10) yes N13 . C14 . H142 . 108.8 no C15 . C14 . H142 . 108.1 no N13 . C14 . H141 . 108.8 no C15 . C14 . H141 . 108.7 no H142 . C14 . H141 . 109.5 no C14 . C15 . O16 . 109.1(10) yes C14 . C15 . H152 . 109.3 no O16 . C15 . H152 . 108.9 no C14 . C15 . H151 . 109.7 no O16 . C15 . H151 . 110.6 no H152 . C15 . H151 . 109.3 no C15 . O16 . C17 . 122.2(9) yes O16 . C17 . C18 . 121.8(9) yes O16 . C17 . C22 . 121.6(11) yes C18 . C17 . C22 . 116.6(10) yes C17 . C18 . C19 . 120.2(10) yes C17 . C18 . H181 . 120.2 no C19 . C18 . H181 . 119.6 no C18 . C19 . C20 . 120.0(11) yes C18 . C19 . H191 . 120.1 no C20 . C19 . H191 . 120.0 no C19 . C20 . C21 . 120.2(10) yes C19 . C20 . O23 . 125.9(10) yes C21 . C20 . O23 . 113.8(9) yes C20 . C21 . C22 . 117.0(10) yes C20 . C21 . H211 . 121.2 no C22 . C21 . H211 . 121.8 no C21 . C22 . C17 . 125.9(11) yes C21 . C22 . H221 . 117.3 no C17 . C22 . H221 . 116.7 no C20 . O23 . C24 . 115.8(8) yes O23 . C24 . C25 . 108.1(9) yes O23 . C24 . H241 . 110.7 no C25 . C24 . H241 . 109.6 no O23 . C24 . H242 . 109.4 no C25 . C24 . H242 . 110.0 no H241 . C24 . H242 . 109.0 no C24 . C25 . O26 . 108.2(8) yes C24 . C25 . H251 . 109.4 no O26 . C25 . H251 . 109.8 no C24 . C25 . H252 . 110.2 no O26 . C25 . H252 . 109.8 no H251 . C25 . H252 . 109.5 no C25 . O26 . C27 . 112.6(8) yes O26 . C27 . C28 . 108.8(8) yes O26 . C27 . H271 . 109.7 no C28 . C27 . H271 . 110.1 no O26 . C27 . H272 . 110.1 no C28 . C27 . H272 . 108.7 no H271 . C27 . H272 . 109.4 no C27 . C28 . O29 . 112.5(10) yes C27 . C28 . H281 . 108.6 no O29 . C28 . H281 . 108.8 no C27 . C28 . H282 . 109.2 no O29 . C28 . H282 . 108.8 no H281 . C28 . H282 . 108.9 no C28 . O29 . C30 . 113.8(9) yes O29 . C30 . C31 . 107.3(9) yes O29 . C30 . H302 . 109.9 no C31 . C30 . H302 . 110.3 no O29 . C30 . H301 . 109.9 no C31 . C30 . H301 . 110.0 no H302 . C30 . H301 . 109.4 no C30 . C31 . O32 . 108.4(9) yes C30 . C31 . H312 . 109.7 no O32 . C31 . H312 . 110.9 no C30 . C31 . H311 . 109.4 no O32 . C31 . H311 . 108.9 no H312 . C31 . H311 . 109.6 no C31 . O32 . C33 . 112.6(8) yes O32 . C33 . C34 . 110.5(9) yes O32 . C33 . H331 . 109.7 no C34 . C33 . H331 . 110.4 no O32 . C33 . H332 . 108.8 no C34 . C33 . H332 . 107.6 no H331 . C33 . H332 . 109.8 no C33 . C34 . O35 . 110.4(10) yes C33 . C34 . H342 . 109.1 no O35 . C34 . H342 . 109.0 no C33 . C34 . H341 . 109.1 no O35 . C34 . H341 . 109.7 no H342 . C34 . H341 . 109.6 no C34 . O35 . C36 . 118.9(9) yes O35 . C36 . C37 . 117.1(10) yes O35 . C36 . C41 . 124.5(10) yes C37 . C36 . C41 . 118.4(10) yes C36 . C37 . C38 . 121.6(11) yes C36 . C37 . H371 . 118.9 no C38 . C37 . H371 . 119.6 no C37 . C38 . C39 . 119.8(10) yes C37 . C38 . H381 . 120.2 no C39 . C38 . H381 . 119.9 no C38 . C39 . C40 . 120.2(10) yes C38 . C39 . O42 . 114.6(9) yes C40 . C39 . O42 . 125.1(11) yes C39 . C40 . C41 . 119.8(10) yes C39 . C40 . H401 . 120.6 no C41 . C40 . H401 . 119.6 no C40 . C41 . C36 . 120.1(10) yes C40 . C41 . H411 . 119.9 no C36 . C41 . H411 . 120.0 no C39 . O42 . C43 . 117.9(8) yes O42 . C43 . C44 . 106.3(8) yes O42 . C43 . H431 . 111.2 no C44 . C43 . H431 . 109.5 no O42 . C43 . H432 . 109.2 no C44 . C43 . H432 . 110.8 no H431 . C43 . H432 . 109.8 no C43 . C44 . N45 . 110.1(8) yes C43 . C44 . H441 . 110.2 no N45 . C44 . H441 . 109.4 no C43 . C44 . H442 . 109.1 no N45 . C44 . H442 . 108.9 no H441 . C44 . H442 . 109.2 no C44 . N45 . C46 . 120.1(8) yes C44 . N45 . H451 . 118.4 no C46 . N45 . H451 . 119.6 no C2 . C46 . N45 . 113.1(8) yes C2 . C46 . O47 . 122.2(10) yes N45 . C46 . O47 . 124.7(10) yes 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 C9 . H91 . O47 2_576 170 0.96 2.53 3.486(15) yes C24 . H241 . O12 2_667 126 0.98 2.57 3.238(15) yes C25 . H251 . O12 2_667 125 0.98 2.49 3.161(15) yes C43 . H431 . O12 1_465 155 0.97 2.53 3.435(15) yes N13 . H131 . O23 2_567 152 0.85 2.27 3.049(15) yes _chemical_name_common . #===END #============================================================================== data_SynAntiPolymorph _database_code_depnum_ccdc_archive 'CCDC 815168' #TrackingRef '- crystallographicdata.cif' #============================================================================== _audit_creation_date 11-01-12 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 039CJS09 _chemical_name_systematic . _chemical_melting_point . _cell_length_a 20.1979(6) _cell_length_b 19.3405(5) _cell_length_c 9.0377(2) _cell_angle_alpha 90 _cell_angle_beta 99.6836(10) _cell_angle_gamma 90 _cell_volume 3480.16(16) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C36 H44 N2 O9 # Dc = 1.24 Fooo = 1392.00 Mu = 0.89 M = 648.75 # Found Formula = C36 H46 N2 O9 # Dc = 1.24 FOOO = 1392.00 Mu = 0.89 M = 650.77 _chemical_formula_sum 'C36 H46 N2 O9' _chemical_formula_moiety 'C36 H46 N2 O9' _chemical_compound_source ? _chemical_formula_weight 650.77 _cell_measurement_reflns_used 7065 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.150 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.210 _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.089 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 25510 _reflns_number_total 7806 _diffrn_reflns_av_R_equivalents 0.046 # Number of reflections without Friedels Law is 13846 # Number of reflections with Friedels Law is 7806 # Theoretical number of reflections is about 8365 _diffrn_reflns_theta_min 5.200 _diffrn_reflns_theta_max 27.954 _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 25.159 _diffrn_measured_fraction_theta_full 0.981 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min 0 _reflns_limit_h_max 26 _reflns_limit_k_min -25 _reflns_limit_k_max 0 _reflns_limit_l_min -11 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 2.56 _oxford_diffrn_Wilson_scale 4.80 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.41 _refine_diff_density_max 0.46 # 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 7805 _refine_ls_number_restraints 0 _refine_ls_number_parameters 424 _oxford_refine_ls_R_factor_ref 0.0900 _refine_ls_wR_factor_ref 0.1308 _refine_ls_goodness_of_fit_ref 0.9514 _refine_ls_shift/su_max 0.0007221 _refine_ls_shift/su_mean 0.0000737 # The values computed from all data _oxford_reflns_number_all 7806 _refine_ls_R_factor_all 0.0900 _refine_ls_wR_factor_all 0.1309 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5469 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_gt 0.1123 # 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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 3.11P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.72587(10) 0.90837(10) 0.9164(2) 0.0255 1.0000 Uani . . . . . . . C2 C 0.69990(9) 0.84198(10) 0.9146(2) 0.0257 1.0000 Uani . . . . . . . C3 C 0.64790(10) 0.82151(10) 0.8006(2) 0.0268 1.0000 Uani . . . . . . . C4 C 0.62036(10) 0.86774(10) 0.6877(2) 0.0271 1.0000 Uani . . . . . . . C5 C 0.64906(10) 0.93321(10) 0.6893(2) 0.0277 1.0000 Uani . . . . . . . C6 C 0.70139(10) 0.95398(10) 0.8004(2) 0.0262 1.0000 Uani . . . . . . . C7 C 0.56107(10) 0.84900(11) 0.5641(2) 0.0323 1.0000 Uani . . . . . . . C8 C 0.57789(13) 0.86893(14) 0.4103(2) 0.0457 1.0000 Uani . . . . . . . C9 C 0.49893(12) 0.88886(13) 0.5927(3) 0.0494 1.0000 Uani . . . . . . . C10 C 0.54529(11) 0.77147(11) 0.5627(2) 0.0367 1.0000 Uani . . . . . . . C11 C 0.73112(10) 1.02407(10) 0.7841(2) 0.0285 1.0000 Uani . . . . . . . O12 O 0.72448(9) 1.05184(8) 0.65989(16) 0.0445 1.0000 Uani . . . . . . . N13 N 0.76339(8) 1.05370(8) 0.90955(18) 0.0287 1.0000 Uani . . . . . . . C14 C 0.79746(10) 1.11991(10) 0.9108(2) 0.0303 1.0000 Uani . . . . . . . C15 C 0.87264(10) 1.11272(10) 0.9411(2) 0.0297 1.0000 Uani . . . . . . . O16 O 0.89161(7) 1.06725(7) 0.83071(15) 0.0322 1.0000 Uani . . . . . . . C17 C 0.95941(10) 1.05640(10) 0.8345(2) 0.0281 1.0000 Uani . . . . . . . C18 C 0.97654(10) 1.00867(10) 0.7331(2) 0.0300 1.0000 Uani . . . . . . . C19 C 1.04295(10) 0.99749(10) 0.7196(2) 0.0309 1.0000 Uani . . . . . . . C20 C 1.09329(10) 1.03451(10) 0.8099(2) 0.0289 1.0000 Uani . . . . . . . C21 C 1.07683(10) 1.08046(11) 0.9154(2) 0.0316 1.0000 Uani . . . . . . . C22 C 1.01008(11) 1.09150(11) 0.9283(2) 0.0317 1.0000 Uani . . . . . . . O23 O 1.16111(7) 1.02863(8) 0.80467(15) 0.0348 1.0000 Uani . . . . . . . C24 C 1.17994(11) 0.99941(12) 0.6735(2) 0.0350 1.0000 Uani . . . . . . . C25 C 1.25411(11) 1.01025(12) 0.6823(2) 0.0349 1.0000 Uani . . . . . . . O26 O 1.28805(7) 0.97149(7) 0.80683(15) 0.0327 1.0000 Uani . . . . . . . C27 C 1.35891(10) 0.97150(12) 0.8152(2) 0.0365 1.0000 Uani . . . . . . . C28 C 1.39123(11) 0.93836(11) 0.9587(3) 0.0373 1.0000 Uani . . . . . . . O29 O 1.37211(8) 0.86772(8) 0.96159(17) 0.0386 1.0000 Uani . . . . . . . C30 C 1.38852(11) 0.83881(12) 1.1075(3) 0.0396 1.0000 Uani . . . . . . . C31 C 1.37159(11) 0.76326(12) 1.1049(3) 0.0415 1.0000 Uani . . . . . . . O32 O 1.30130(7) 0.75454(7) 1.08112(19) 0.0386 1.0000 Uani . . . . . . . C33 C 1.28341(11) 0.68311(11) 1.0774(3) 0.0372 1.0000 Uani . . . . . . . C34 C 1.20963(11) 0.67605(11) 1.0208(2) 0.0338 1.0000 Uani . . . . . . . O35 O 1.17327(7) 0.69424(8) 1.13868(16) 0.0352 1.0000 Uani . . . . . . . C36 C 1.10435(10) 0.68752(10) 1.1081(2) 0.0275 1.0000 Uani . . . . . . . C37 C 1.06840(10) 0.66142(10) 0.9749(2) 0.0286 1.0000 Uani . . . . . . . C38 C 0.99863(10) 0.65877(10) 0.9554(2) 0.0290 1.0000 Uani . . . . . . . C39 C 0.96421(10) 0.68117(10) 1.0667(2) 0.0278 1.0000 Uani . . . . . . . C40 C 1.00020(10) 0.70604(11) 1.2007(2) 0.0314 1.0000 Uani . . . . . . . C41 C 1.06987(11) 0.70873(11) 1.2206(2) 0.0312 1.0000 Uani . . . . . . . O42 O 0.89493(7) 0.67725(8) 1.03231(15) 0.0356 1.0000 Uani . . . . . . . C43 C 0.85791(10) 0.69194(11) 1.1498(2) 0.0309 1.0000 Uani . . . . . . . C44 C 0.78422(10) 0.67951(10) 1.0886(2) 0.0296 1.0000 Uani . . . . . . . N45 N 0.75328(8) 0.73266(8) 0.98514(17) 0.0277 1.0000 Uani . . . . . . . C46 C 0.73109(10) 0.79197(10) 1.0341(2) 0.0254 1.0000 Uani . . . . . . . O47 O 0.73554(8) 0.80657(7) 1.16866(15) 0.0349 1.0000 Uani . . . . . . . H11 H 0.7609 0.9215 0.9966 0.0301 1.0000 Uiso R . . . . . . H31 H 0.6322 0.7747 0.8007 0.0324 1.0000 Uiso R . . . . . . H51 H 0.6332 0.9648 0.6148 0.0325 1.0000 Uiso R . . . . . . H83 H 0.5406 0.8544 0.3333 0.0687 1.0000 Uiso R . . . . . . H82 H 0.5831 0.9192 0.4038 0.0684 1.0000 Uiso R . . . . . . H81 H 0.6192 0.8447 0.3955 0.0691 1.0000 Uiso R . . . . . . H93 H 0.4617 0.8780 0.5123 0.0735 1.0000 Uiso R . . . . . . H92 H 0.5090 0.9374 0.5921 0.0736 1.0000 Uiso R . . . . . . H91 H 0.4880 0.8753 0.6892 0.0733 1.0000 Uiso R . . . . . . H101 H 0.5105 0.7612 0.4770 0.0546 1.0000 Uiso R . . . . . . H102 H 0.5856 0.7444 0.5527 0.0536 1.0000 Uiso R . . . . . . H103 H 0.5289 0.7580 0.6560 0.0551 1.0000 Uiso R . . . . . . H142 H 0.7837 1.1475 0.9893 0.0355 1.0000 Uiso R . . . . . . H141 H 0.7841 1.1421 0.8134 0.0358 1.0000 Uiso R . . . . . . H152 H 0.8933 1.1579 0.9337 0.0361 1.0000 Uiso R . . . . . . H151 H 0.8881 1.0933 1.0423 0.0348 1.0000 Uiso R . . . . . . H181 H 0.9426 0.9843 0.6727 0.0371 1.0000 Uiso R . . . . . . H191 H 1.0540 0.9656 0.6491 0.0369 1.0000 Uiso R . . . . . . H211 H 1.1126 1.1044 0.9784 0.0391 1.0000 Uiso R . . . . . . H221 H 0.9975 1.1227 1.0015 0.0385 1.0000 Uiso R . . . . . . H241 H 1.1549 1.0227 0.5851 0.0414 1.0000 Uiso R . . . . . . H242 H 1.1684 0.9500 0.6694 0.0416 1.0000 Uiso R . . . . . . H252 H 1.2663 1.0596 0.6995 0.0414 1.0000 Uiso R . . . . . . H251 H 1.2676 0.9931 0.5908 0.0413 1.0000 Uiso R . . . . . . H272 H 1.3763 1.0193 0.8136 0.0438 1.0000 Uiso R . . . . . . H271 H 1.3700 0.9467 0.7274 0.0442 1.0000 Uiso R . . . . . . H282 H 1.4410 0.9422 0.9652 0.0450 1.0000 Uiso R . . . . . . H281 H 1.3779 0.9632 1.0451 0.0442 1.0000 Uiso R . . . . . . H301 H 1.4374 0.8449 1.1436 0.0466 1.0000 Uiso R . . . . . . H302 H 1.3634 0.8640 1.1741 0.0470 1.0000 Uiso R . . . . . . H311 H 1.3910 0.7430 1.2018 0.0501 1.0000 Uiso R . . . . . . H312 H 1.3896 0.7400 1.0227 0.0507 1.0000 Uiso R . . . . . . H331 H 1.2954 0.6616 1.1744 0.0449 1.0000 Uiso R . . . . . . H332 H 1.3069 0.6593 1.0073 0.0447 1.0000 Uiso R . . . . . . H341 H 1.1956 0.7075 0.9338 0.0408 1.0000 Uiso R . . . . . . H342 H 1.1999 0.6277 0.9909 0.0411 1.0000 Uiso R . . . . . . H371 H 1.0916 0.6457 0.8986 0.0342 1.0000 Uiso R . . . . . . H381 H 0.9732 0.6414 0.8617 0.0362 1.0000 Uiso R . . . . . . H401 H 0.9778 0.7221 1.2784 0.0382 1.0000 Uiso R . . . . . . H411 H 1.0942 0.7251 1.3130 0.0374 1.0000 Uiso R . . . . . . H432 H 0.8650 0.7406 1.1849 0.0372 1.0000 Uiso R . . . . . . H431 H 0.8716 0.6595 1.2360 0.0366 1.0000 Uiso R . . . . . . H442 H 0.7607 0.6775 1.1736 0.0355 1.0000 Uiso R . . . . . . H441 H 0.7795 0.6357 1.0345 0.0359 1.0000 Uiso R . . . . . . H131 H 0.7613 1.0345 0.9954 0.0348 1.0000 Uiso R . . . . . . H451 H 0.7514 0.7260 0.8881 0.0339 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 C1 0.0249(10) 0.0295(10) 0.0225(8) -0.0023(7) 0.0048(7) 0.0006(8) C2 0.0260(10) 0.0290(10) 0.0231(9) 0.0004(7) 0.0072(7) 0.0019(8) C3 0.0253(10) 0.0281(10) 0.0278(9) 0.0002(8) 0.0067(8) -0.0019(8) C4 0.0249(10) 0.0316(10) 0.0249(9) -0.0015(8) 0.0050(7) 0.0000(8) C5 0.0281(10) 0.0298(10) 0.0249(9) 0.0024(8) 0.0035(8) 0.0040(8) C6 0.0281(10) 0.0272(10) 0.0241(9) -0.0001(7) 0.0071(7) 0.0000(8) C7 0.0250(10) 0.0359(11) 0.0341(10) 0.0003(9) -0.0009(8) -0.0010(9) C8 0.0512(14) 0.0526(14) 0.0293(11) 0.0044(10) -0.0051(10) -0.0135(12) C9 0.0290(12) 0.0453(14) 0.0702(17) -0.0035(12) -0.0027(11) 0.0054(10) C10 0.0317(11) 0.0390(12) 0.0375(11) -0.0015(9) 0.0000(9) -0.0061(9) C11 0.0334(11) 0.0275(10) 0.0252(9) -0.0001(8) 0.0062(8) 0.0014(8) O12 0.0689(12) 0.0350(8) 0.0279(7) 0.0044(6) 0.0037(7) -0.0118(8) N13 0.0317(9) 0.0283(8) 0.0267(8) 0.0010(7) 0.0067(7) -0.0048(7) C14 0.0312(11) 0.0248(10) 0.0354(10) -0.0008(8) 0.0072(8) -0.0015(8) C15 0.0321(11) 0.0251(10) 0.0319(10) -0.0027(8) 0.0055(8) -0.0011(8) O16 0.0271(7) 0.0364(8) 0.0334(7) -0.0071(6) 0.0056(6) -0.0004(6) C17 0.0286(10) 0.0288(10) 0.0268(9) 0.0029(8) 0.0047(8) 0.0015(8) C18 0.0303(10) 0.0276(10) 0.0305(10) -0.0014(8) 0.0006(8) -0.0016(8) C19 0.0346(11) 0.0278(10) 0.0295(10) -0.0047(8) 0.0031(8) 0.0037(9) C20 0.0284(10) 0.0301(10) 0.0274(9) 0.0014(8) 0.0024(8) 0.0044(8) C21 0.0294(10) 0.0365(11) 0.0272(9) -0.0051(8) 0.0000(8) -0.0004(9) C22 0.0329(11) 0.0352(11) 0.0267(9) -0.0049(8) 0.0044(8) 0.0011(9) O23 0.0282(7) 0.0460(9) 0.0294(7) -0.0090(6) 0.0028(6) 0.0055(6) C24 0.0358(11) 0.0424(12) 0.0268(10) -0.0055(9) 0.0056(8) 0.0000(9) C25 0.0380(12) 0.0417(12) 0.0267(10) 0.0005(9) 0.0100(9) 0.0015(9) O26 0.0276(7) 0.0374(8) 0.0348(7) 0.0050(6) 0.0096(6) 0.0027(6) C27 0.0278(11) 0.0401(12) 0.0440(12) 0.0024(10) 0.0133(9) -0.0024(9) C28 0.0287(11) 0.0351(12) 0.0481(12) -0.0016(9) 0.0062(9) -0.0054(9) O29 0.0374(8) 0.0331(8) 0.0435(8) -0.0008(6) 0.0018(7) -0.0030(7) C30 0.0298(11) 0.0397(12) 0.0468(13) 0.0028(10) -0.0010(9) 0.0004(9) C31 0.0285(11) 0.0373(12) 0.0568(14) 0.0035(10) 0.0017(10) 0.0025(9) O32 0.0259(7) 0.0291(8) 0.0612(10) -0.0015(7) 0.0085(7) 0.0006(6) C33 0.0321(11) 0.0277(10) 0.0531(13) -0.0006(9) 0.0104(10) 0.0021(9) C34 0.0332(11) 0.0306(11) 0.0397(11) -0.0027(9) 0.0125(9) 0.0005(9) O35 0.0276(7) 0.0416(8) 0.0369(8) -0.0083(6) 0.0069(6) -0.0022(6) C36 0.0255(10) 0.0244(10) 0.0325(10) -0.0002(8) 0.0050(8) -0.0015(8) C37 0.0309(10) 0.0274(10) 0.0291(10) -0.0021(8) 0.0099(8) -0.0026(8) C38 0.0306(10) 0.0305(10) 0.0263(9) -0.0032(8) 0.0054(8) -0.0018(8) C39 0.0257(10) 0.0304(10) 0.0272(9) 0.0012(8) 0.0040(8) 0.0010(8) C40 0.0323(11) 0.0348(11) 0.0276(9) -0.0034(8) 0.0067(8) 0.0027(9) C41 0.0335(11) 0.0320(11) 0.0274(10) -0.0038(8) 0.0035(8) -0.0007(9) O42 0.0266(7) 0.0534(9) 0.0272(7) -0.0061(6) 0.0053(6) 0.0024(7) C43 0.0302(11) 0.0391(11) 0.0243(9) 0.0013(8) 0.0072(8) 0.0041(9) C44 0.0297(10) 0.0304(10) 0.0291(10) 0.0041(8) 0.0060(8) 0.0038(8) N45 0.0298(9) 0.0324(9) 0.0211(7) 0.0004(6) 0.0047(6) 0.0031(7) C46 0.0251(9) 0.0286(10) 0.0222(9) 0.0014(7) 0.0031(7) -0.0026(8) O47 0.0486(9) 0.0333(8) 0.0224(7) 0.0000(6) 0.0050(6) 0.0012(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4605(7) 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 . C2 . 1.386(3) yes C1 . C6 . 1.396(3) yes C1 . H11 . 0.958 no C2 . C3 . 1.399(3) yes C2 . C46 . 1.507(3) yes C3 . C4 . 1.400(3) yes C3 . H31 . 0.959 no C4 . C5 . 1.392(3) yes C4 . C7 . 1.537(3) yes C5 . C6 . 1.389(3) yes C5 . H51 . 0.927 no C6 . C11 . 1.500(3) yes C7 . C8 . 1.535(3) yes C7 . C9 . 1.532(3) yes C7 . C10 . 1.533(3) yes C8 . H83 . 0.977 no C8 . H82 . 0.981 no C8 . H81 . 0.986 no C9 . H93 . 0.977 no C9 . H92 . 0.961 no C9 . H91 . 0.970 no C10 . H101 . 0.974 no C10 . H102 . 0.985 no C10 . H103 . 0.992 no C11 . O12 . 1.231(2) yes C11 . N13 . 1.338(2) yes N13 . C14 . 1.453(2) yes N13 . H131 . 0.868 no C14 . C15 . 1.503(3) yes C14 . H142 . 0.965 no C14 . H141 . 0.975 no C15 . O16 . 1.430(2) yes C15 . H152 . 0.976 no C15 . H151 . 0.990 no O16 . C17 . 1.380(2) yes C17 . C18 . 1.385(3) yes C17 . C22 . 1.391(3) yes C18 . C19 . 1.384(3) yes C18 . H181 . 0.930 no C19 . C20 . 1.391(3) yes C19 . H191 . 0.940 no C20 . C21 . 1.384(3) yes C20 . O23 . 1.383(2) yes C21 . C22 . 1.389(3) yes C21 . H211 . 0.960 no C22 . H221 . 0.960 no O23 . C24 . 1.422(2) yes C24 . C25 . 1.501(3) yes C24 . H241 . 0.980 no C24 . H242 . 0.984 no C25 . O26 . 1.428(2) yes C25 . H252 . 0.991 no C25 . H251 . 0.972 no O26 . C27 . 1.420(2) yes C27 . C28 . 1.495(3) yes C27 . H272 . 0.990 no C27 . H271 . 0.985 no C28 . O29 . 1.421(3) yes C28 . H282 . 0.999 no C28 . H281 . 0.991 no O29 . C30 . 1.420(3) yes C30 . C31 . 1.500(3) yes C30 . H301 . 0.993 no C30 . H302 . 0.980 no C31 . O32 . 1.410(3) yes C31 . H311 . 0.979 no C31 . H312 . 0.988 no O32 . C33 . 1.427(2) yes C33 . C34 . 1.498(3) yes C33 . H331 . 0.964 no C33 . H332 . 0.970 no C34 . O35 . 1.436(2) yes C34 . H341 . 0.996 no C34 . H342 . 0.985 no O35 . C36 . 1.379(2) yes C36 . C37 . 1.391(3) yes C36 . C41 . 1.388(3) yes C37 . C38 . 1.391(3) yes C37 . H371 . 0.947 no C38 . C39 . 1.385(3) yes C38 . H381 . 0.974 no C39 . C40 . 1.389(3) yes C39 . O42 . 1.384(2) yes C40 . C41 . 1.389(3) yes C40 . H401 . 0.949 no C41 . H411 . 0.949 no O42 . C43 . 1.426(2) yes C43 . C44 . 1.517(3) yes C43 . H432 . 0.996 no C43 . H431 . 1.003 no C44 . N45 . 1.458(2) yes C44 . H442 . 0.970 no C44 . H441 . 0.976 no N45 . C46 . 1.334(2) yes N45 . H451 . 0.881 no C46 . O47 . 1.237(2) 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 C2 . C1 . C6 . 119.40(17) yes C2 . C1 . H11 . 119.0 no C6 . C1 . H11 . 121.6 no C1 . C2 . C3 . 120.45(17) yes C1 . C2 . C46 . 118.30(16) yes C3 . C2 . C46 . 121.19(17) yes C2 . C3 . C4 . 120.87(18) yes C2 . C3 . H31 . 118.2 no C4 . C3 . H31 . 120.9 no C3 . C4 . C5 . 117.36(17) yes C3 . C4 . C7 . 122.99(18) yes C5 . C4 . C7 . 119.65(17) yes C4 . C5 . C6 . 122.42(18) yes C4 . C5 . H51 . 120.0 no C6 . C5 . H51 . 117.6 no C1 . C6 . C5 . 119.37(18) yes C1 . C6 . C11 . 123.23(17) yes C5 . C6 . C11 . 117.33(17) yes C4 . C7 . C8 . 109.56(17) yes C4 . C7 . C9 . 108.62(18) yes C8 . C7 . C9 . 109.8(2) yes C4 . C7 . C10 . 111.87(17) yes C8 . C7 . C10 . 108.38(18) yes C9 . C7 . C10 . 108.58(18) yes C7 . C8 . H83 . 108.1 no C7 . C8 . H82 . 110.2 no H83 . C8 . H82 . 108.7 no C7 . C8 . H81 . 108.9 no H83 . C8 . H81 . 109.6 no H82 . C8 . H81 . 111.2 no C7 . C9 . H93 . 108.4 no C7 . C9 . H92 . 108.1 no H93 . C9 . H92 . 110.1 no C7 . C9 . H91 . 109.4 no H93 . C9 . H91 . 110.3 no H92 . C9 . H91 . 110.5 no C7 . C10 . H101 . 109.1 no C7 . C10 . H102 . 110.3 no H101 . C10 . H102 . 108.4 no C7 . C10 . H103 . 110.4 no H101 . C10 . H103 . 108.8 no H102 . C10 . H103 . 109.8 no C6 . C11 . O12 . 119.99(17) yes C6 . C11 . N13 . 116.73(16) yes O12 . C11 . N13 . 123.27(18) yes C11 . N13 . C14 . 123.13(16) yes C11 . N13 . H131 . 118.9 no C14 . N13 . H131 . 117.8 no N13 . C14 . C15 . 112.49(16) yes N13 . C14 . H142 . 107.4 no C15 . C14 . H142 . 108.8 no N13 . C14 . H141 . 108.8 no C15 . C14 . H141 . 108.8 no H142 . C14 . H141 . 110.5 no C14 . C15 . O16 . 108.08(16) yes C14 . C15 . H152 . 109.6 no O16 . C15 . H152 . 109.6 no C14 . C15 . H151 . 110.8 no O16 . C15 . H151 . 109.4 no H152 . C15 . H151 . 109.4 no C15 . O16 . C17 . 117.21(15) yes O16 . C17 . C18 . 116.23(17) yes O16 . C17 . C22 . 124.49(18) yes C18 . C17 . C22 . 119.24(18) yes C17 . C18 . C19 . 121.08(18) yes C17 . C18 . H181 . 119.0 no C19 . C18 . H181 . 119.9 no C18 . C19 . C20 . 119.43(18) yes C18 . C19 . H191 . 120.4 no C20 . C19 . H191 . 120.2 no C19 . C20 . C21 . 119.89(19) yes C19 . C20 . O23 . 124.62(18) yes C21 . C20 . O23 . 115.49(17) yes C20 . C21 . C22 . 120.37(18) yes C20 . C21 . H211 . 118.3 no C22 . C21 . H211 . 121.3 no C17 . C22 . C21 . 119.91(18) yes C17 . C22 . H221 . 118.2 no C21 . C22 . H221 . 121.8 no C20 . O23 . C24 . 117.82(15) yes O23 . C24 . C25 . 107.76(16) yes O23 . C24 . H241 . 108.9 no C25 . C24 . H241 . 110.7 no O23 . C24 . H242 . 108.9 no C25 . C24 . H242 . 111.4 no H241 . C24 . H242 . 109.2 no C24 . C25 . O26 . 108.11(17) yes C24 . C25 . H252 . 111.2 no O26 . C25 . H252 . 108.0 no C24 . C25 . H251 . 109.2 no O26 . C25 . H251 . 109.0 no H252 . C25 . H251 . 111.3 no C25 . O26 . C27 . 112.82(15) yes O26 . C27 . C28 . 109.58(17) yes O26 . C27 . H272 . 110.8 no C28 . C27 . H272 . 108.0 no O26 . C27 . H271 . 108.7 no C28 . C27 . H271 . 111.4 no H272 . C27 . H271 . 108.3 no C27 . C28 . O29 . 110.34(18) yes C27 . C28 . H282 . 107.9 no O29 . C28 . H282 . 110.1 no C27 . C28 . H281 . 109.8 no O29 . C28 . H281 . 109.9 no H282 . C28 . H281 . 108.8 no C28 . O29 . C30 . 111.95(16) yes O29 . C30 . C31 . 110.61(19) yes O29 . C30 . H301 . 108.8 no C31 . C30 . H301 . 109.4 no O29 . C30 . H302 . 108.1 no C31 . C30 . H302 . 110.7 no H301 . C30 . H302 . 109.1 no C30 . C31 . O32 . 109.87(18) yes C30 . C31 . H311 . 108.6 no O32 . C31 . H311 . 109.2 no C30 . C31 . H312 . 110.1 no O32 . C31 . H312 . 108.6 no H311 . C31 . H312 . 110.4 no C31 . O32 . C33 . 111.34(16) yes O32 . C33 . C34 . 109.25(17) yes O32 . C33 . H331 . 111.9 no C34 . C33 . H331 . 110.7 no O32 . C33 . H332 . 109.0 no C34 . C33 . H332 . 107.6 no H331 . C33 . H332 . 108.3 no C33 . C34 . O35 . 109.15(18) yes C33 . C34 . H341 . 110.4 no O35 . C34 . H341 . 108.8 no C33 . C34 . H342 . 108.8 no O35 . C34 . H342 . 109.4 no H341 . C34 . H342 . 110.2 no C34 . O35 . C36 . 116.94(15) yes O35 . C36 . C37 . 124.75(18) yes O35 . C36 . C41 . 116.06(17) yes C37 . C36 . C41 . 119.19(18) yes C36 . C37 . C38 . 119.55(18) yes C36 . C37 . H371 . 119.8 no C38 . C37 . H371 . 120.7 no C37 . C38 . C39 . 121.19(18) yes C37 . C38 . H381 . 119.9 no C39 . C38 . H381 . 118.9 no C38 . C39 . C40 . 119.25(18) yes C38 . C39 . O42 . 115.59(17) yes C40 . C39 . O42 . 125.16(18) yes C39 . C40 . C41 . 119.72(19) yes C39 . C40 . H401 . 120.9 no C41 . C40 . H401 . 119.4 no C40 . C41 . C36 . 121.09(18) yes C40 . C41 . H411 . 119.3 no C36 . C41 . H411 . 119.6 no C39 . O42 . C43 . 117.31(15) yes O42 . C43 . C44 . 107.58(16) yes O42 . C43 . H432 . 111.2 no C44 . C43 . H432 . 110.2 no O42 . C43 . H431 . 110.0 no C44 . C43 . H431 . 108.1 no H432 . C43 . H431 . 109.8 no C43 . C44 . N45 . 114.24(17) yes C43 . C44 . H442 . 107.4 no N45 . C44 . H442 . 108.8 no C43 . C44 . H441 . 109.2 no N45 . C44 . H441 . 107.2 no H442 . C44 . H441 . 110.0 no C44 . N45 . C46 . 121.68(16) yes C44 . N45 . H451 . 118.5 no C46 . N45 . H451 . 119.7 no C2 . C46 . N45 . 115.93(16) yes C2 . C46 . O47 . 120.71(17) yes N45 . C46 . O47 . 123.36(17) yes 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 . O23 2_777 171 0.96 2.38 3.334(3) yes C25 . H251 . O12 2_776 168 0.97 2.46 3.412(3) yes C33 . H332 . O12 3_746 132 0.97 2.59 3.310(3) yes N13 . H131 . O23 2_777 137 0.87 2.50 3.195(3) yes N13 . H131 . O26 2_777 148 0.87 2.19 2.964(3) yes N45 . H451 . O47 4_564 169 0.88 2.05 2.922(3) yes _chemical_name_common . #===END #============================================================================== data_AntiAntiPolymorph _database_code_depnum_ccdc_archive 'CCDC 815169' #TrackingRef '- crystallographicdata.cif' #============================================================================== _audit_creation_date 11-01-27 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 010CJS11 _chemical_name_systematic . _chemical_melting_point . # start Validation Reply Form _vrf_DIFMN02_AntiAntiPolymorph ; PROBLEM: The minimum difference density is < -0.1*ZMAX*2.00 RESPONSE: The residual electron density corresponds to a very minor disordered component at C(27) and C(28). However, attempts to model this using partial occupancies did not result in a stable model. ; _vrf_DIFMX01_AntiAntiPolymorph ; PROBLEM: The maximum difference density is > 0.1*ZMAX*2.00 RESPONSE: The residual electron density corresponds to a very minor disordered component at C(27) and C(28). However, attempts to model this using partial occupancies did not result in a stable model. ; _vrf_PLAT097_AntiAntiPolymorph ; PROBLEM: Large Reported Max. (Positive) Residual Density 1.25 eA-3 RESPONSE: The residual electron density corresponds to a very minor disordered component at C(27) and C(28). However, attempts to model this using partial occupancies did not result in a stable model. ; _vrf_PLAT098_AntiAntiPolymorph ; PROBLEM: Large Reported Min. (Negative) Residual Density -0.51 eA-3 RESPONSE: The residual electron density corresponds to a very minor disordered component at C(27) and C(28). However, attempts to model this using partial occupancies did not result in a stable model. ; # end Validation Reply Form _cell_length_a 10.2724(2) _cell_length_b 13.2776(2) _cell_length_c 13.7434(3) _cell_angle_alpha 68.6691(10) _cell_angle_beta 83.2934(9) _cell_angle_gamma 70.4090(9) _cell_volume 1644.98(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol 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' _cell_formula_units_Z 2 # Given Formula = C36 H46 N2 O9 # Dc = 1.31 Fooo = 696.00 Mu = 0.94 M = 650.77 # Found Formula = C36 H46 N2 O9 # Dc = 1.31 FOOO = 696.00 Mu = 0.94 M = 650.77 _chemical_formula_sum 'C36 H46 N2 O9' _chemical_formula_moiety 'C36 H46 N2 O9' _chemical_compound_source ? _chemical_formula_weight 650.77 _cell_measurement_reflns_used 6675 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.250 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_max 0.280 _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.094 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 23513 _reflns_number_total 7348 _diffrn_reflns_av_R_equivalents 0.021 # Number of reflections without Friedels Law is 12606 # Number of reflections with Friedels Law is 7348 # Theoretical number of reflections is about 7469 _diffrn_reflns_theta_min 5.233 _diffrn_reflns_theta_max 27.382 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.287 _diffrn_measured_fraction_theta_full 0.987 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -15 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 2.23 _oxford_diffrn_Wilson_scale 0.52 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.51 _refine_diff_density_max 1.25 # 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 7343 _refine_ls_number_restraints 0 _refine_ls_number_parameters 424 _oxford_refine_ls_R_factor_ref 0.0658 _refine_ls_wR_factor_ref 0.1655 _refine_ls_goodness_of_fit_ref 0.9080 _refine_ls_shift/su_max 0.0003834 _refine_ls_shift/su_mean 0.0000336 # The values computed from all data _oxford_reflns_number_all 7344 _refine_ls_R_factor_all 0.0658 _refine_ls_wR_factor_all 0.1656 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6226 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_gt 0.1558 # 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: 114. 184. 108. 43.4 9.60 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. 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 C1 C 0.38034(18) 0.42221(15) 1.14399(13) 0.0218 1.0000 Uani . . . . . . . C2 C 0.51540(17) 0.37076(14) 1.17930(13) 0.0214 1.0000 Uani . . . . . . . C3 C 0.59478(17) 0.43746(15) 1.18070(14) 0.0218 1.0000 Uani . . . . . . . C4 C 0.54034(17) 0.55643(15) 1.14606(13) 0.0212 1.0000 Uani . . . . . . . C5 C 0.40495(18) 0.60663(15) 1.10623(13) 0.0221 1.0000 Uani . . . . . . . C6 C 0.32495(17) 0.54082(15) 1.10456(13) 0.0215 1.0000 Uani . . . . . . . C7 C 0.62222(18) 0.63232(15) 1.15051(14) 0.0235 1.0000 Uani . . . . . . . C8 C 0.6325(3) 0.7155(2) 1.04091(18) 0.0435 1.0000 Uani . . . . . . . C9 C 0.7677(2) 0.56345(19) 1.1937(2) 0.0422 1.0000 Uani . . . . . . . C10 C 0.5467(2) 0.7014(2) 1.22048(19) 0.0372 1.0000 Uani . . . . . . . C11 C 0.17841(18) 0.58909(15) 1.06529(14) 0.0227 1.0000 Uani . . . . . . . O12 O 0.09808(15) 0.53345(13) 1.09842(12) 0.0367 1.0000 Uani . . . . . . . N13 N 0.14111(15) 0.69377(13) 0.99223(11) 0.0223 1.0000 Uani . . . . . . . C14 C -0.00033(18) 0.74985(16) 0.95389(14) 0.0243 1.0000 Uani . . . . . . . C15 C -0.03329(18) 0.71405(16) 0.86914(14) 0.0236 1.0000 Uani . . . . . . . O16 O 0.04629(14) 0.75359(13) 0.77902(10) 0.0288 1.0000 Uani . . . . . . . C17 C 0.00933(18) 0.75538(16) 0.68406(14) 0.0241 1.0000 Uani . . . . . . . C18 C 0.0651(2) 0.81900(18) 0.59605(15) 0.0300 1.0000 Uani . . . . . . . C19 C 0.0353(2) 0.82513(18) 0.49750(15) 0.0304 1.0000 Uani . . . . . . . C20 C -0.0508(2) 0.76819(16) 0.48744(14) 0.0264 1.0000 Uani . . . . . . . C21 C -0.1065(2) 0.70482(17) 0.57546(15) 0.0286 1.0000 Uani . . . . . . . C22 C -0.07525(19) 0.69709(16) 0.67482(15) 0.0266 1.0000 Uani . . . . . . . O23 O -0.08045(16) 0.78357(12) 0.38589(11) 0.0328 1.0000 Uani . . . . . . . C24 C -0.0943(2) 0.68908(18) 0.36604(16) 0.0331 1.0000 Uani . . . . . . . C25 C 0.0437(3) 0.6127(2) 0.3470(2) 0.0495 1.0000 Uani . . . . . . . O26 O 0.12130(19) 0.55804(16) 0.44300(17) 0.0559 1.0000 Uani . . . . . . . C27 C 0.2480(3) 0.5743(2) 0.4444(3) 0.0587 1.0000 Uani . . . . 1 . . C28 C 0.3641(3) 0.4921(2) 0.4112(3) 0.0580 1.0000 Uani . . . . 1 . . O29 O 0.38590(17) 0.38093(13) 0.48640(13) 0.0432 1.0000 Uani . . . . . . . C30 C 0.4870(3) 0.2993(2) 0.45194(19) 0.0472 1.0000 Uani . . . . . . . C31 C 0.5131(2) 0.18581(19) 0.53631(17) 0.0357 1.0000 Uani . . . . . . . O32 O 0.63240(15) 0.11082(13) 0.50676(11) 0.0356 1.0000 Uani . . . . . . . C33 C 0.6652(2) -0.00477(18) 0.57412(16) 0.0319 1.0000 Uani . . . . . . . C34 C 0.6710(2) -0.02275(17) 0.68797(15) 0.0278 1.0000 Uani . . . . . . . O35 O 0.76832(14) 0.02606(12) 0.70294(10) 0.0286 1.0000 Uani . . . . . . . C36 C 0.77075(18) 0.03279(15) 0.79941(14) 0.0231 1.0000 Uani . . . . . . . C37 C 0.85758(19) 0.09008(16) 0.81046(15) 0.0250 1.0000 Uani . . . . . . . C38 C 0.86660(19) 0.10213(16) 0.90443(15) 0.0253 1.0000 Uani . . . . . . . C39 C 0.78953(18) 0.05795(15) 0.99003(14) 0.0237 1.0000 Uani . . . . . . . C40 C 0.70493(19) -0.00014(15) 0.98039(15) 0.0252 1.0000 Uani . . . . . . . C41 C 0.69569(19) -0.01290(15) 0.88491(15) 0.0251 1.0000 Uani . . . . . . . O42 O 0.80310(14) 0.07855(12) 1.07902(10) 0.0278 1.0000 Uani . . . . . . . C43 C 0.7390(2) 0.02420(15) 1.17239(14) 0.0264 1.0000 Uani . . . . . . . C44 C 0.7606(2) 0.06640(15) 1.25595(14) 0.0254 1.0000 Uani . . . . . . . N45 N 0.70317(15) 0.19028(12) 1.22538(12) 0.0223 1.0000 Uani . . . . . . . C46 C 0.56615(18) 0.24244(15) 1.21536(14) 0.0235 1.0000 Uani . . . . . . . O47 O 0.48424(15) 0.18891(12) 1.23156(13) 0.0364 1.0000 Uani . . . . . . . H11 H 0.3275 0.3755 1.1486 0.0271 1.0000 Uiso R . . . . . . H31 H 0.6872 0.4024 1.2046 0.0246 1.0000 Uiso R . . . . . . H51 H 0.3669 0.6860 1.0818 0.0266 1.0000 Uiso R . . . . . . H83 H 0.6811 0.7629 1.0447 0.0632 1.0000 Uiso R . . . . . . H82 H 0.5422 0.7604 1.0096 0.0644 1.0000 Uiso R . . . . . . H81 H 0.6832 0.6754 0.9955 0.0649 1.0000 Uiso R . . . . . . H93 H 0.8193 0.6126 1.1954 0.0616 1.0000 Uiso R . . . . . . H92 H 0.7688 0.5089 1.2631 0.0619 1.0000 Uiso R . . . . . . H91 H 0.8176 0.5242 1.1483 0.0629 1.0000 Uiso R . . . . . . H101 H 0.5917 0.7560 1.2186 0.0529 1.0000 Uiso R . . . . . . H102 H 0.5471 0.6510 1.2938 0.0556 1.0000 Uiso R . . . . . . H103 H 0.4512 0.7458 1.1985 0.0548 1.0000 Uiso R . . . . . . H142 H -0.0151 0.8287 0.9251 0.0276 1.0000 Uiso R . . . . . . H141 H -0.0633 0.7317 1.0125 0.0289 1.0000 Uiso R . . . . . . H152 H -0.1304 0.7500 0.8566 0.0278 1.0000 Uiso R . . . . . . H151 H -0.0124 0.6305 0.8936 0.0266 1.0000 Uiso R . . . . . . H181 H 0.1229 0.8586 0.6022 0.0364 1.0000 Uiso R . . . . . . H191 H 0.0711 0.8689 0.4382 0.0372 1.0000 Uiso R . . . . . . H211 H -0.1627 0.6631 0.5702 0.0347 1.0000 Uiso R . . . . . . H221 H -0.1129 0.6543 0.7349 0.0303 1.0000 Uiso R . . . . . . H241 H -0.1515 0.7212 0.3035 0.0384 1.0000 Uiso R . . . . . . H242 H -0.1411 0.6484 0.4182 0.0406 1.0000 Uiso R . . . . . . H252 H 0.0919 0.6566 0.2914 0.0608 1.0000 Uiso R . . . . . . H251 H 0.0269 0.5562 0.3220 0.0612 1.0000 Uiso R . . . . . . H272 H 0.2460 0.6540 0.4018 0.0687 1.0000 Uiso R . . . 1 . . H271 H 0.2679 0.5601 0.5197 0.0703 1.0000 Uiso R . . . 1 . . H282 H 0.4486 0.5140 0.4087 0.0694 1.0000 Uiso R . . . 1 . . H281 H 0.3348 0.5000 0.3401 0.0703 1.0000 Uiso R . . . 1 . . H301 H 0.5724 0.3203 0.4334 0.0568 1.0000 Uiso R . . . . . . H302 H 0.4463 0.2987 0.3902 0.0570 1.0000 Uiso R . . . . . . H311 H 0.5292 0.1915 0.6042 0.0451 1.0000 Uiso R . . . . . . H312 H 0.4362 0.1559 0.5480 0.0423 1.0000 Uiso R . . . . . . H331 H 0.7548 -0.0472 0.5523 0.0367 1.0000 Uiso R . . . . . . H332 H 0.5954 -0.0357 0.5662 0.0382 1.0000 Uiso R . . . . . . H341 H 0.6953 -0.1058 0.7273 0.0339 1.0000 Uiso R . . . . . . H342 H 0.5783 0.0124 0.7117 0.0338 1.0000 Uiso R . . . . . . H371 H 0.9115 0.1178 0.7538 0.0323 1.0000 Uiso R . . . . . . H381 H 0.9251 0.1405 0.9131 0.0307 1.0000 Uiso R . . . . . . H401 H 0.6536 -0.0309 1.0381 0.0315 1.0000 Uiso R . . . . . . H411 H 0.6435 -0.0575 0.8811 0.0298 1.0000 Uiso R . . . . . . H432 H 0.7810 -0.0599 1.1945 0.0312 1.0000 Uiso R . . . . . . H431 H 0.6409 0.0419 1.1587 0.0302 1.0000 Uiso R . . . . . . H442 H 0.8597 0.0464 1.2705 0.0302 1.0000 Uiso R . . . . . . H441 H 0.7144 0.0319 1.3198 0.0278 1.0000 Uiso R . . . . . . H131 H 0.2016 0.7299 0.9697 0.0264 1.0000 Uiso R . . . . . . H451 H 0.7582 0.2309 1.2137 0.0302 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 C1 0.0210(8) 0.0232(8) 0.0238(8) -0.0084(7) 0.0003(6) -0.0100(6) C2 0.0211(8) 0.0206(8) 0.0230(8) -0.0083(6) 0.0020(6) -0.0072(6) C3 0.0179(7) 0.0232(8) 0.0245(8) -0.0088(7) -0.0004(6) -0.0060(6) C4 0.0200(8) 0.0234(8) 0.0226(8) -0.0094(6) 0.0012(6) -0.0087(6) C5 0.0213(8) 0.0203(8) 0.0232(8) -0.0057(6) -0.0016(6) -0.0064(6) C6 0.0188(8) 0.0241(8) 0.0213(8) -0.0065(6) -0.0009(6) -0.0076(6) C7 0.0220(8) 0.0240(8) 0.0284(9) -0.0107(7) 0.0001(7) -0.0102(7) C8 0.0578(14) 0.0493(13) 0.0355(11) -0.0082(10) 0.0017(10) -0.0395(12) C9 0.0255(10) 0.0340(11) 0.0730(16) -0.0211(11) -0.0119(10) -0.0099(8) C10 0.0364(11) 0.0414(12) 0.0484(12) -0.0284(10) 0.0091(9) -0.0193(9) C11 0.0208(8) 0.0245(8) 0.0229(8) -0.0066(7) -0.0017(6) -0.0085(7) O12 0.0257(7) 0.0331(8) 0.0447(8) 0.0024(6) -0.0083(6) -0.0156(6) N13 0.0194(7) 0.0246(7) 0.0225(7) -0.0055(6) -0.0025(5) -0.0085(6) C14 0.0204(8) 0.0262(9) 0.0244(8) -0.0083(7) -0.0027(6) -0.0047(7) C15 0.0192(8) 0.0299(9) 0.0220(8) -0.0078(7) -0.0003(6) -0.0092(7) O16 0.0276(6) 0.0436(8) 0.0213(6) -0.0105(6) 0.0007(5) -0.0199(6) C17 0.0220(8) 0.0289(9) 0.0220(8) -0.0092(7) -0.0022(6) -0.0078(7) C18 0.0314(9) 0.0372(10) 0.0271(9) -0.0117(8) 0.0015(7) -0.0180(8) C19 0.0356(10) 0.0348(10) 0.0229(9) -0.0092(7) 0.0033(7) -0.0158(8) C20 0.0288(9) 0.0259(9) 0.0234(8) -0.0101(7) -0.0034(7) -0.0047(7) C21 0.0300(9) 0.0294(9) 0.0308(9) -0.0113(8) -0.0025(7) -0.0132(8) C22 0.0265(9) 0.0288(9) 0.0250(9) -0.0082(7) 0.0005(7) -0.0109(7) O23 0.0485(9) 0.0263(7) 0.0240(7) -0.0091(5) -0.0073(6) -0.0097(6) C24 0.0403(11) 0.0310(10) 0.0304(10) -0.0128(8) -0.0089(8) -0.0087(8) C25 0.0613(16) 0.0377(12) 0.0473(14) -0.0216(11) 0.0018(12) -0.0057(11) O26 0.0409(9) 0.0429(10) 0.0717(13) -0.0148(9) -0.0142(9) 0.0010(8) C27 0.0655(18) 0.0399(14) 0.0653(18) -0.0131(13) -0.0039(14) -0.0145(13) C28 0.0472(14) 0.0379(13) 0.0657(18) 0.0033(12) 0.0074(13) -0.0102(11) O29 0.0376(8) 0.0303(8) 0.0464(9) -0.0028(7) 0.0044(7) -0.0046(6) C30 0.0419(13) 0.0422(13) 0.0370(12) -0.0021(10) 0.0069(10) -0.0027(10) C31 0.0340(10) 0.0357(11) 0.0320(10) -0.0113(8) 0.0028(8) -0.0060(9) O32 0.0332(8) 0.0377(8) 0.0277(7) -0.0096(6) 0.0010(6) -0.0032(6) C33 0.0314(10) 0.0327(10) 0.0339(10) -0.0160(8) -0.0056(8) -0.0062(8) C34 0.0270(9) 0.0293(9) 0.0304(9) -0.0107(7) -0.0030(7) -0.0116(7) O35 0.0308(7) 0.0357(7) 0.0255(6) -0.0120(6) 0.0006(5) -0.0171(6) C36 0.0218(8) 0.0214(8) 0.0253(8) -0.0085(7) -0.0016(6) -0.0048(6) C37 0.0238(8) 0.0259(8) 0.0272(9) -0.0100(7) 0.0024(7) -0.0101(7) C38 0.0230(8) 0.0269(9) 0.0304(9) -0.0126(7) 0.0013(7) -0.0106(7) C39 0.0245(8) 0.0217(8) 0.0250(8) -0.0097(7) -0.0011(6) -0.0054(7) C40 0.0259(8) 0.0224(8) 0.0266(9) -0.0069(7) 0.0020(7) -0.0090(7) C41 0.0253(8) 0.0229(8) 0.0284(9) -0.0080(7) -0.0011(7) -0.0098(7) O42 0.0333(7) 0.0315(7) 0.0255(7) -0.0140(5) 0.0041(5) -0.0156(6) C43 0.0328(9) 0.0218(8) 0.0250(9) -0.0079(7) 0.0020(7) -0.0099(7) C44 0.0289(9) 0.0203(8) 0.0241(8) -0.0068(7) -0.0033(7) -0.0039(7) N45 0.0226(7) 0.0200(7) 0.0252(7) -0.0086(6) 0.0001(6) -0.0071(6) C46 0.0224(8) 0.0216(8) 0.0271(8) -0.0080(7) 0.0008(6) -0.0085(7) O47 0.0258(7) 0.0244(7) 0.0595(10) -0.0119(6) 0.0012(6) -0.0121(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.445(9) 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 . C2 . 1.381(2) yes C1 . C6 . 1.396(2) yes C1 . H11 . 0.933 no C2 . C3 . 1.396(2) yes C2 . C46 . 1.507(2) yes C3 . C4 . 1.399(2) yes C3 . H31 . 0.944 no C4 . C5 . 1.403(2) yes C4 . C7 . 1.533(2) yes C5 . C6 . 1.393(2) yes C5 . H51 . 0.934 no C6 . C11 . 1.503(2) yes C7 . C8 . 1.527(3) yes C7 . C9 . 1.523(3) yes C7 . C10 . 1.536(3) yes C8 . H83 . 0.943 no C8 . H82 . 0.968 no C8 . H81 . 0.962 no C9 . H93 . 0.976 no C9 . H92 . 0.964 no C9 . H91 . 0.952 no C10 . H101 . 0.974 no C10 . H102 . 0.985 no C10 . H103 . 0.976 no C11 . O12 . 1.229(2) yes C11 . N13 . 1.343(2) yes N13 . C14 . 1.453(2) yes N13 . H131 . 0.870 no C14 . C15 . 1.516(2) yes C14 . H142 . 0.939 no C14 . H141 . 0.983 no C15 . O16 . 1.434(2) yes C15 . H152 . 0.956 no C15 . H151 . 0.988 no O16 . C17 . 1.391(2) yes C17 . C18 . 1.387(3) yes C17 . C22 . 1.385(3) yes C18 . C19 . 1.391(3) yes C18 . H181 . 0.943 no C19 . C20 . 1.388(3) yes C19 . H191 . 0.931 no C20 . C21 . 1.385(3) yes C20 . O23 . 1.390(2) yes C21 . C22 . 1.399(3) yes C21 . H211 . 0.947 no C22 . H221 . 0.941 no O23 . C24 . 1.430(2) yes C24 . C25 . 1.499(3) yes C24 . H241 . 0.975 no C24 . H242 . 0.921 no C25 . O26 . 1.436(3) yes C25 . H252 . 0.975 no C25 . H251 . 0.998 no O26 . C27 . 1.392(4) yes C27 . C28 . 1.478(4) yes C27 . H272 . 1.001 no C27 . H271 . 1.015 no C28 . O29 . 1.421(3) yes C28 . H282 . 0.997 no C28 . H281 . 1.014 no O29 . C30 . 1.408(3) yes C30 . C31 . 1.489(3) yes C30 . H301 . 0.987 no C30 . H302 . 0.993 no C31 . O32 . 1.421(2) yes C31 . H311 . 1.000 no C31 . H312 . 0.970 no O32 . C33 . 1.421(3) yes C33 . C34 . 1.500(3) yes C33 . H331 . 0.982 no C33 . H332 . 0.971 no C34 . O35 . 1.429(2) yes C34 . H341 . 0.991 no C34 . H342 . 0.985 no O35 . C36 . 1.364(2) yes C36 . C37 . 1.403(2) yes C36 . C41 . 1.388(3) yes C37 . C38 . 1.375(3) yes C37 . H371 . 0.936 no C38 . C39 . 1.395(3) yes C38 . H381 . 0.949 no C39 . C40 . 1.385(3) yes C39 . O42 . 1.378(2) yes C40 . C41 . 1.400(3) yes C40 . H401 . 0.941 no C41 . H411 . 0.940 no O42 . C43 . 1.431(2) yes C43 . C44 . 1.514(3) yes C43 . H432 . 0.993 no C43 . H431 . 0.980 no C44 . N45 . 1.461(2) yes C44 . H442 . 0.987 no C44 . H441 . 0.981 no N45 . C46 . 1.342(2) yes N45 . H451 . 0.870 no C46 . O47 . 1.227(2) 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 C2 . C1 . C6 . 120.30(15) yes C2 . C1 . H11 . 118.2 no C6 . C1 . H11 . 121.5 no C1 . C2 . C3 . 119.91(16) yes C1 . C2 . C46 . 115.66(15) yes C3 . C2 . C46 . 124.42(15) yes C2 . C3 . C4 . 121.16(16) yes C2 . C3 . H31 . 119.9 no C4 . C3 . H31 . 118.9 no C3 . C4 . C5 . 117.70(15) yes C3 . C4 . C7 . 122.69(15) yes C5 . C4 . C7 . 119.61(15) yes C4 . C5 . C6 . 121.52(16) yes C4 . C5 . H51 . 119.2 no C6 . C5 . H51 . 119.3 no C1 . C6 . C5 . 119.28(15) yes C1 . C6 . C11 . 116.52(15) yes C5 . C6 . C11 . 124.17(15) yes C4 . C7 . C8 . 109.52(15) yes C4 . C7 . C9 . 112.29(15) yes C8 . C7 . C9 . 108.59(18) yes C4 . C7 . C10 . 109.57(15) yes C8 . C7 . C10 . 108.40(18) yes C9 . C7 . C10 . 108.37(17) yes C7 . C8 . H83 . 108.9 no C7 . C8 . H82 . 111.6 no H83 . C8 . H82 . 110.8 no C7 . C8 . H81 . 110.9 no H83 . C8 . H81 . 107.6 no H82 . C8 . H81 . 107.1 no C7 . C9 . H93 . 111.6 no C7 . C9 . H92 . 112.9 no H93 . C9 . H92 . 108.1 no C7 . C9 . H91 . 109.1 no H93 . C9 . H91 . 105.8 no H92 . C9 . H91 . 109.0 no C7 . C10 . H101 . 110.9 no C7 . C10 . H102 . 110.8 no H101 . C10 . H102 . 107.3 no C7 . C10 . H103 . 112.7 no H101 . C10 . H103 . 106.1 no H102 . C10 . H103 . 108.6 no C6 . C11 . O12 . 120.65(16) yes C6 . C11 . N13 . 117.09(15) yes O12 . C11 . N13 . 122.26(16) yes C11 . N13 . C14 . 120.94(15) yes C11 . N13 . H131 . 119.5 no C14 . N13 . H131 . 119.5 no N13 . C14 . C15 . 113.91(14) yes N13 . C14 . H142 . 108.3 no C15 . C14 . H142 . 107.1 no N13 . C14 . H141 . 108.8 no C15 . C14 . H141 . 107.8 no H142 . C14 . H141 . 111.0 no C14 . C15 . O16 . 107.55(14) yes C14 . C15 . H152 . 105.4 no O16 . C15 . H152 . 112.1 no C14 . C15 . H151 . 110.5 no O16 . C15 . H151 . 111.7 no H152 . C15 . H151 . 109.3 no C15 . O16 . C17 . 117.74(13) yes O16 . C17 . C18 . 115.56(16) yes O16 . C17 . C22 . 123.85(16) yes C18 . C17 . C22 . 120.58(17) yes C17 . C18 . C19 . 119.86(18) yes C17 . C18 . H181 . 120.7 no C19 . C18 . H181 . 119.5 no C18 . C19 . C20 . 119.94(18) yes C18 . C19 . H191 . 120.1 no C20 . C19 . H191 . 120.0 no C19 . C20 . C21 . 120.07(17) yes C19 . C20 . O23 . 116.03(17) yes C21 . C20 . O23 . 123.84(17) yes C20 . C21 . C22 . 120.20(17) yes C20 . C21 . H211 . 121.2 no C22 . C21 . H211 . 118.6 no C21 . C22 . C17 . 119.35(17) yes C21 . C22 . H221 . 120.6 no C17 . C22 . H221 . 120.0 no C20 . O23 . C24 . 118.06(15) yes O23 . C24 . C25 . 111.16(19) yes O23 . C24 . H241 . 106.4 no C25 . C24 . H241 . 109.4 no O23 . C24 . H242 . 112.7 no C25 . C24 . H242 . 111.0 no H241 . C24 . H242 . 106.0 no C24 . C25 . O26 . 108.5(2) yes C24 . C25 . H252 . 110.1 no O26 . C25 . H252 . 111.6 no C24 . C25 . H251 . 107.7 no O26 . C25 . H251 . 111.8 no H252 . C25 . H251 . 107.1 no C25 . O26 . C27 . 118.3(2) yes O26 . C27 . C28 . 113.2(3) yes O26 . C27 . H272 . 112.1 no C28 . C27 . H272 . 110.0 no O26 . C27 . H271 . 107.1 no C28 . C27 . H271 . 106.3 no H272 . C27 . H271 . 107.9 no C27 . C28 . O29 . 109.5(2) yes C27 . C28 . H282 . 107.6 no O29 . C28 . H282 . 108.4 no C27 . C28 . H281 . 104.4 no O29 . C28 . H281 . 113.4 no H282 . C28 . H281 . 113.3 no C28 . O29 . C30 . 110.69(19) yes O29 . C30 . C31 . 108.60(18) yes O29 . C30 . H301 . 110.2 no C31 . C30 . H301 . 111.2 no O29 . C30 . H302 . 105.9 no C31 . C30 . H302 . 109.6 no H301 . C30 . H302 . 111.2 no C30 . C31 . O32 . 106.62(17) yes C30 . C31 . H311 . 110.0 no O32 . C31 . H311 . 110.6 no C30 . C31 . H312 . 113.6 no O32 . C31 . H312 . 110.3 no H311 . C31 . H312 . 105.9 no C31 . O32 . C33 . 114.29(16) yes O32 . C33 . C34 . 114.74(16) yes O32 . C33 . H331 . 107.8 no C34 . C33 . H331 . 109.6 no O32 . C33 . H332 . 109.1 no C34 . C33 . H332 . 106.8 no H331 . C33 . H332 . 108.8 no C33 . C34 . O35 . 108.91(16) yes C33 . C34 . H341 . 107.9 no O35 . C34 . H341 . 113.0 no C33 . C34 . H342 . 109.5 no O35 . C34 . H342 . 111.0 no H341 . C34 . H342 . 106.3 no C34 . O35 . C36 . 116.36(14) yes O35 . C36 . C37 . 115.87(16) yes O35 . C36 . C41 . 124.99(16) yes C37 . C36 . C41 . 119.14(17) yes C36 . C37 . C38 . 120.35(17) yes C36 . C37 . H371 . 119.2 no C38 . C37 . H371 . 120.4 no C37 . C38 . C39 . 120.64(16) yes C37 . C38 . H381 . 121.3 no C39 . C38 . H381 . 118.1 no C38 . C39 . C40 . 119.49(17) yes C38 . C39 . O42 . 115.58(16) yes C40 . C39 . O42 . 124.92(16) yes C39 . C40 . C41 . 120.06(17) yes C39 . C40 . H401 . 119.9 no C41 . C40 . H401 . 120.1 no C40 . C41 . C36 . 120.30(16) yes C40 . C41 . H411 . 119.0 no C36 . C41 . H411 . 120.5 no C39 . O42 . C43 . 117.80(14) yes O42 . C43 . C44 . 107.48(15) yes O42 . C43 . H432 . 110.4 no C44 . C43 . H432 . 110.3 no O42 . C43 . H431 . 109.5 no C44 . C43 . H431 . 112.2 no H432 . C43 . H431 . 107.1 no C43 . C44 . N45 . 112.06(14) yes C43 . C44 . H442 . 111.6 no N45 . C44 . H442 . 106.6 no C43 . C44 . H441 . 108.4 no N45 . C44 . H441 . 108.5 no H442 . C44 . H441 . 109.6 no C44 . N45 . C46 . 120.83(15) yes C44 . N45 . H451 . 119.7 no C46 . N45 . H451 . 119.4 no C2 . C46 . N45 . 117.58(15) yes C2 . C46 . O47 . 120.49(16) yes N45 . C46 . O47 . 121.89(16) yes 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 C15 . H151 . O12 2_567 145 0.99 2.57 3.431(3) yes N13 . H131 . O42 2_667 135 0.87 2.37 3.050(3) yes N45 . H451 . O16 2_667 152 0.87 2.10 2.898(3) yes _chemical_name_common . #===END #============================================================================== data_MeOH _database_code_depnum_ccdc_archive 'CCDC 815170' #TrackingRef '- crystallographicdata.cif' #============================================================================== _audit_creation_date 11-01-20 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 046CJS10 _chemical_name_systematic . _chemical_melting_point . # start Validation Reply Form _vrf_PLAT029_MeOH ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.88 RESPONSE: The crystals were small and diffracted poorly at high angle, even using synchrotron radiation. The maximum possible resolution data were obtained. ; # end Validation Reply Form _cell_length_a 8.864(13) _cell_length_b 9.554(14) _cell_length_c 21.89(4) _cell_angle_alpha 82.63(4) _cell_angle_beta 82.94(5) _cell_angle_gamma 74.70(5) _cell_volume 1766(5) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol 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' _cell_formula_units_Z 2 # Given Formula = C36 H46 N2 O9 # Dc = 1.22 Fooo = 732.00 Mu = 0.88 M = 650.77 # Found Formula = C37 H50 N2 O10 # Dc = 1.28 FOOO = 732.00 Mu = 0.93 M = 682.81 _chemical_formula_sum 'C37 H50 N2 O10' _chemical_formula_moiety 'C36 H46 N2 O9, C H4 O' _chemical_compound_source ? _chemical_formula_weight 682.81 _cell_measurement_reflns_used 3870 _cell_measurement_theta_min 2 _cell_measurement_theta_max 32 _cell_measurement_temperature 150 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.012 _exptl_crystal_size_mid 0.014 _exptl_crystal_size_max 0.061 _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 732.000 _exptl_absorpt_coefficient_mu 0.093 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrystalClear (Rigaku, 1997--2009)' _exptl_absorpt_correction_T_min 0.71 _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 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_ambient_temperature 150 _diffrn_reflns_number 10117 _reflns_number_total 10117 _diffrn_reflns_av_R_equivalents 0.070 # Number of reflections without Friedels Law is 10117 # Number of reflections with Friedels Law is 10117 # Theoretical number of reflections is about 5237 _diffrn_reflns_theta_min 1.884 _diffrn_reflns_theta_max 32.982 _diffrn_measured_fraction_theta_max 0.759 _diffrn_reflns_theta_full 25.066 _diffrn_measured_fraction_theta_full 0.878 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _reflns_limit_h_min -11 _reflns_limit_h_max 12 _reflns_limit_k_min -14 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 32 _oxford_diffrn_Wilson_B_factor 2.76 _oxford_diffrn_Wilson_scale 4.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.47 _refine_diff_density_max 0.46 # 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 4587 _refine_ls_number_restraints 30 _refine_ls_number_parameters 462 _oxford_refine_ls_R_factor_ref 0.1223 _refine_ls_wR_factor_ref 0.3010 _refine_ls_goodness_of_fit_ref 1.0092 _refine_ls_shift/su_max 0.0001663 _refine_ls_shift/su_mean 0.0000223 # The values computed from all data _oxford_reflns_number_all 4587 _refine_ls_R_factor_all 0.1223 _refine_ls_wR_factor_all 0.3010 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3751 _refine_ls_R_factor_gt 0.1070 _refine_ls_wR_factor_gt 0.2861 # 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= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.17P)^2^ + 4.32P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/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. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C -0.0758(6) 0.0633(6) 0.8008(2) 0.0388 1.0000 Uani . . . . . . . C2 C -0.1264(6) 0.1568(6) 0.8475(2) 0.0390 1.0000 Uani . . . . . . . C3 C -0.0219(7) 0.1555(6) 0.8909(2) 0.0417 1.0000 Uani . . . . . . . C4 C 0.1267(7) 0.0650(6) 0.8887(2) 0.0426 1.0000 Uani . . . . . . . C5 C 0.1744(6) -0.0232(6) 0.8412(2) 0.0376 1.0000 Uani . . . . . . . C6 C 0.0757(6) -0.0267(6) 0.7969(2) 0.0356 1.0000 Uani . . . . . . . C7 C 0.2453(7) 0.0717(7) 0.9345(2) 0.0513 1.0000 Uani . . . . . . . C8 C 0.3562(10) 0.1583(10) 0.8999(3) 0.0796 1.0000 Uani . . . . . . . C9 C 0.1659(9) 0.1393(10) 0.9918(3) 0.0743 1.0000 Uani . . . . . . . C10 C 0.3393(10) -0.0854(10) 0.9542(3) 0.0858 1.0000 Uani . . . . . . . C11 C 0.1402(6) -0.1180(6) 0.7448(2) 0.0365 1.0000 Uani . . . . . . . O12 O 0.2807(5) -0.1803(5) 0.73832(18) 0.0556 1.0000 Uani . . . . . . . N13 N 0.0417(5) -0.1269(5) 0.70465(18) 0.0401 1.0000 Uani . . . . . . . C14 C 0.0907(7) -0.2108(6) 0.6520(2) 0.0420 1.0000 Uani . . . . . . . C15 C 0.1519(7) -0.1230(6) 0.5968(2) 0.0385 1.0000 Uani . . . . . . . O16 O 0.1825(5) -0.2113(4) 0.54689(15) 0.0420 1.0000 Uani . . . . . . . C17 C 0.2166(6) -0.1501(5) 0.4889(2) 0.0369 1.0000 Uani . . . . . . . C18 C 0.2605(6) -0.0185(6) 0.4762(2) 0.0386 1.0000 Uani . . . . . . . C19 C 0.2951(6) 0.0336(6) 0.4152(2) 0.0368 1.0000 Uani . . . . . . . C20 C 0.2850(6) -0.0438(5) 0.3671(2) 0.0339 1.0000 Uani . . . . . . . C21 C 0.2398(6) -0.1746(6) 0.3802(2) 0.0378 1.0000 Uani . . . . . . . C22 C 0.2080(6) -0.2271(6) 0.4405(2) 0.0374 1.0000 Uani . . . . . . . O23 O 0.3099(4) 0.0012(4) 0.30466(14) 0.0394 1.0000 Uani . . . . . . . C24 C 0.3792(7) 0.1225(6) 0.2890(2) 0.0426 1.0000 Uani . . . . . . . C25 C 0.3770(7) 0.1645(7) 0.2213(2) 0.0456 1.0000 Uani . . . . . . . O26 O 0.2214(4) 0.2362(4) 0.20868(15) 0.0420 1.0000 Uani . . . . . . . C27 C 0.2105(7) 0.3006(7) 0.1464(2) 0.0504 1.0000 Uani . . . . . . . C28 C 0.0454(8) 0.3902(7) 0.1381(2) 0.0530 1.0000 Uani . . . . . . . O29 O 0.0019(5) 0.5186(4) 0.16957(16) 0.0560 1.0000 Uani . . . . . . . C30 C -0.0581(7) 0.4954(6) 0.2321(2) 0.0437 1.0000 Uani . . . . . . . C31 C -0.1174(8) 0.6414(6) 0.2562(2) 0.0497 1.0000 Uani . . . . . . . O32 O -0.1865(4) 0.6204(4) 0.31762(15) 0.0416 1.0000 Uani . . . . . . . C33 C -0.2542(7) 0.7547(6) 0.3432(2) 0.0450 1.0000 Uani . . . . . . . C34 C -0.3291(7) 0.7258(6) 0.4069(2) 0.0452 1.0000 Uani . . . . . . . O35 O -0.2083(4) 0.6802(4) 0.44880(15) 0.0419 1.0000 Uani . . . . . . . C36 C -0.2551(6) 0.6405(6) 0.5093(2) 0.0362 1.0000 Uani . . . . . . . C37 C -0.1355(6) 0.6023(5) 0.5491(2) 0.0348 1.0000 Uani . . . . . . . C38 C -0.1663(6) 0.5570(5) 0.6104(2) 0.0355 1.0000 Uani . . . . . . . C39 C -0.3188(6) 0.5495(5) 0.6338(2) 0.0327 1.0000 Uani . . . . . . . C40 C -0.4374(6) 0.5930(5) 0.5946(2) 0.0375 1.0000 Uani . . . . . . . C41 C -0.4050(6) 0.6352(6) 0.5322(2) 0.0381 1.0000 Uani . . . . . . . O42 O -0.3371(4) 0.5047(4) 0.69571(15) 0.0404 1.0000 Uani . . . . . . . C43 C -0.4873(6) 0.4844(6) 0.7212(2) 0.0428 1.0000 Uani . . . . . . . C44 C -0.4769(7) 0.4377(6) 0.7887(3) 0.0495 1.0000 Uani . . . . . . . N45 N -0.3462(6) 0.3063(5) 0.7971(2) 0.0482 1.0000 Uani . . . . . . . C46 C -0.2791(7) 0.2682(6) 0.8498(2) 0.0448 1.0000 Uani . . . . . . . O47 O -0.3367(5) 0.3267(5) 0.8965(2) 0.0658 1.0000 Uani . . . . . . . O102 O -0.2130(15) 0.4445(16) 0.9909(6) 0.1723 0.774(12) Uani D U P . 1 . . H11 H -0.1443 0.0635 0.7717 0.0491 1.0000 Uiso R . . . . . . H31 H -0.0560 0.2186 0.9220 0.0508 1.0000 Uiso R . . . . . . H51 H 0.2779 -0.0837 0.8387 0.0471 1.0000 Uiso R . . . . . . H83 H 0.4262 0.1669 0.9288 0.1220 1.0000 Uiso R . . . . . . H82 H 0.2951 0.2542 0.8864 0.1218 1.0000 Uiso R . . . . . . H81 H 0.4163 0.1094 0.8649 0.1221 1.0000 Uiso R . . . . . . H93 H 0.2453 0.1271 1.0202 0.1129 1.0000 Uiso R . . . . . . H92 H 0.1182 0.2426 0.9818 0.1129 1.0000 Uiso R . . . . . . H91 H 0.0858 0.0908 1.0111 0.1130 1.0000 Uiso R . . . . . . H101 H 0.4112 -0.0845 0.9833 0.1263 1.0000 Uiso R . . . . . . H102 H 0.2663 -0.1411 0.9739 0.1263 1.0000 Uiso R . . . . . . H103 H 0.3983 -0.1314 0.9185 0.1261 1.0000 Uiso R . . . . . . H142 H 0.1728 -0.2990 0.6632 0.0508 1.0000 Uiso R . . . . . . H141 H 0.0006 -0.2380 0.6413 0.0512 1.0000 Uiso R . . . . . . H152 H 0.2516 -0.1040 0.6042 0.0488 1.0000 Uiso R . . . . . . H151 H 0.0741 -0.0315 0.5867 0.0491 1.0000 Uiso R . . . . . . H181 H 0.2666 0.0360 0.5092 0.0484 1.0000 Uiso R . . . . . . H191 H 0.3239 0.1215 0.4065 0.0469 1.0000 Uiso R . . . . . . H211 H 0.2317 -0.2261 0.3479 0.0477 1.0000 Uiso R . . . . . . H221 H 0.1779 -0.3151 0.4494 0.0468 1.0000 Uiso R . . . . . . H241 H 0.3182 0.2045 0.3106 0.0529 1.0000 Uiso R . . . . . . H242 H 0.4862 0.0975 0.3008 0.0531 1.0000 Uiso R . . . . . . H251 H 0.4449 0.2301 0.2080 0.0573 1.0000 Uiso R . . . . . . H252 H 0.4145 0.0781 0.1984 0.0569 1.0000 Uiso R . . . . . . H271 H 0.2830 0.3624 0.1372 0.0618 1.0000 Uiso R . . . . . . H272 H 0.2393 0.2239 0.1187 0.0623 1.0000 Uiso R . . . . . . H281 H 0.0368 0.4201 0.0942 0.0637 1.0000 Uiso R . . . . . . H282 H -0.0282 0.3300 0.1534 0.0639 1.0000 Uiso R . . . . . . H302 H 0.0256 0.4355 0.2556 0.0542 1.0000 Uiso R . . . . . . H301 H -0.1429 0.4466 0.2343 0.0545 1.0000 Uiso R . . . . . . H312 H -0.0312 0.6865 0.2563 0.0611 1.0000 Uiso R . . . . . . H311 H -0.1930 0.7052 0.2303 0.0610 1.0000 Uiso R . . . . . . H331 H -0.1733 0.8058 0.3451 0.0569 1.0000 Uiso R . . . . . . H332 H -0.3339 0.8149 0.3172 0.0573 1.0000 Uiso R . . . . . . H342 H -0.4036 0.8155 0.4191 0.0560 1.0000 Uiso R . . . . . . H341 H -0.3839 0.6502 0.4080 0.0560 1.0000 Uiso R . . . . . . H371 H -0.0335 0.6077 0.5337 0.0440 1.0000 Uiso R . . . . . . H381 H -0.0858 0.5313 0.6371 0.0440 1.0000 Uiso R . . . . . . H401 H -0.5393 0.5934 0.6099 0.0466 1.0000 Uiso R . . . . . . H411 H -0.4849 0.6606 0.5061 0.0483 1.0000 Uiso R . . . . . . H431 H -0.5673 0.5744 0.7164 0.0539 1.0000 Uiso R . . . . . . H432 H -0.5133 0.4105 0.7006 0.0535 1.0000 Uiso R . . . . . . H441 H -0.4578 0.5156 0.8086 0.0608 1.0000 Uiso R . . . . . . H442 H -0.5750 0.4185 0.8071 0.0612 1.0000 Uiso R . . . . . . H131 H -0.0577 -0.0993 0.7157 0.0489 1.0000 Uiso R . . . . . . H451 H -0.3016 0.2630 0.7651 0.0612 1.0000 Uiso R . . . . . . O104 O -0.486(6) 0.459(5) 1.057(2) 0.1783 0.226(12) Uani D U P . -2 . . C101 C -0.317(2) 0.475(3) 1.0454(8) 0.1786 0.774(12) Uani D U P . 1 . . C103 C -0.420(9) 0.525(7) 1.001(3) 0.1790 0.226(12) Uani D U P . -2 . . H1021 H -0.2489 0.4103 0.9634 0.2028 0.774(12) Uiso R . P . 1 . . H1011 H -0.2643 0.5124 1.0723 0.2101 0.774(12) Uiso R . P . 1 . . H1012 H -0.3454 0.3905 1.0656 0.2101 0.774(12) Uiso R . P . 1 . . H1013 H -0.4098 0.5473 1.0349 0.2101 0.774(12) Uiso R . P . 1 . . H1031 H -0.3427 0.4609 0.9765 0.2114 0.226(12) Uiso R . P . -2 . . H1032 H -0.3757 0.5973 1.0124 0.2114 0.226(12) Uiso R . P . -2 . . H1033 H -0.5073 0.5698 0.9785 0.2114 0.226(12) Uiso R . P . -2 . . H1041 H -0.5546 0.5156 1.0789 0.2111 0.226(12) Uiso R . P . -2 . . 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 0.040(3) 0.036(3) 0.042(3) -0.002(2) -0.010(2) -0.011(2) C2 0.035(3) 0.041(3) 0.042(3) -0.002(2) -0.003(2) -0.011(2) C3 0.050(4) 0.046(3) 0.032(3) -0.004(2) -0.001(2) -0.018(3) C4 0.043(3) 0.052(3) 0.036(3) 0.001(2) -0.007(2) -0.019(3) C5 0.031(3) 0.039(3) 0.042(3) -0.006(2) -0.005(2) -0.008(2) C6 0.033(3) 0.036(3) 0.038(3) -0.001(2) -0.005(2) -0.011(2) C7 0.050(4) 0.073(4) 0.037(3) -0.007(3) -0.007(2) -0.023(3) C8 0.087(6) 0.111(7) 0.061(4) -0.010(4) -0.012(4) -0.056(5) C9 0.078(5) 0.108(6) 0.050(4) -0.021(4) -0.016(3) -0.035(5) C10 0.094(6) 0.105(7) 0.069(5) -0.002(4) -0.046(4) -0.030(5) C11 0.033(3) 0.038(3) 0.038(3) -0.006(2) -0.006(2) -0.007(2) O12 0.034(3) 0.065(3) 0.068(3) -0.029(2) -0.0101(18) 0.001(2) N13 0.035(3) 0.039(3) 0.045(2) -0.0091(18) -0.0053(19) -0.003(2) C14 0.039(3) 0.041(3) 0.045(3) -0.008(2) -0.006(2) -0.007(2) C15 0.039(3) 0.038(3) 0.040(3) -0.006(2) -0.007(2) -0.011(2) O16 0.051(2) 0.036(2) 0.037(2) -0.0071(14) -0.0052(15) -0.0073(17) C17 0.037(3) 0.030(3) 0.043(3) -0.002(2) -0.010(2) -0.006(2) C18 0.040(3) 0.043(3) 0.036(3) -0.009(2) -0.010(2) -0.010(2) C19 0.037(3) 0.027(3) 0.048(3) -0.005(2) -0.008(2) -0.008(2) C20 0.032(3) 0.030(3) 0.037(3) -0.0057(19) -0.004(2) -0.002(2) C21 0.036(3) 0.036(3) 0.044(3) -0.011(2) -0.005(2) -0.008(2) C22 0.035(3) 0.030(3) 0.049(3) -0.006(2) -0.006(2) -0.007(2) O23 0.041(2) 0.038(2) 0.0382(19) -0.0070(14) -0.0063(15) -0.0070(17) C24 0.040(3) 0.037(3) 0.053(3) -0.001(2) -0.007(2) -0.013(2) C25 0.041(3) 0.052(4) 0.042(3) -0.003(2) 0.000(2) -0.010(3) O26 0.038(2) 0.044(2) 0.041(2) -0.0029(15) -0.0037(15) -0.0067(17) C27 0.058(4) 0.053(4) 0.039(3) -0.004(2) -0.008(3) -0.011(3) C28 0.063(4) 0.053(4) 0.040(3) -0.008(2) -0.006(3) -0.007(3) O29 0.080(3) 0.043(2) 0.041(2) -0.0053(16) 0.0034(19) -0.011(2) C30 0.046(3) 0.043(3) 0.037(3) -0.005(2) -0.001(2) -0.004(3) C31 0.063(4) 0.039(3) 0.045(3) -0.003(2) 0.001(3) -0.011(3) O32 0.045(2) 0.035(2) 0.043(2) -0.0035(14) -0.0068(16) -0.0059(16) C33 0.051(4) 0.038(3) 0.040(3) -0.005(2) -0.005(2) 0.001(3) C34 0.047(4) 0.038(3) 0.047(3) -0.005(2) -0.012(2) -0.002(3) O35 0.036(2) 0.047(2) 0.041(2) -0.0044(15) -0.0043(15) -0.0060(17) C36 0.036(3) 0.030(3) 0.039(3) -0.0084(19) -0.005(2) 0.000(2) C37 0.025(3) 0.035(3) 0.045(3) -0.011(2) -0.003(2) -0.004(2) C38 0.034(3) 0.033(3) 0.041(3) -0.013(2) -0.010(2) -0.004(2) C39 0.026(3) 0.029(3) 0.041(3) -0.0095(19) -0.004(2) -0.001(2) C40 0.020(3) 0.029(3) 0.064(3) -0.007(2) -0.006(2) -0.004(2) C41 0.034(3) 0.039(3) 0.041(3) -0.006(2) -0.008(2) -0.004(2) O42 0.034(2) 0.040(2) 0.046(2) -0.0049(15) -0.0072(15) -0.0054(16) C43 0.028(3) 0.042(3) 0.053(3) 0.000(2) -0.005(2) -0.002(2) C44 0.040(4) 0.041(3) 0.059(3) -0.003(2) -0.001(3) 0.002(3) N45 0.044(3) 0.049(3) 0.042(3) -0.0090(19) -0.006(2) 0.008(2) C46 0.052(4) 0.043(3) 0.041(3) -0.005(2) -0.001(3) -0.016(3) O47 0.057(3) 0.074(3) 0.059(3) -0.026(2) -0.009(2) 0.007(2) O102 0.153(9) 0.200(11) 0.174(10) -0.096(8) 0.005(7) -0.035(8) O104 0.157(10) 0.203(12) 0.180(12) -0.091(10) 0.010(8) -0.032(10) C101 0.155(11) 0.202(12) 0.183(11) -0.092(9) 0.010(7) -0.030(9) C103 0.158(11) 0.203(13) 0.181(12) -0.090(10) 0.011(8) -0.031(11) _refine_ls_extinction_coef 660(160) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.569(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 . C2 . 1.398(8) yes C1 . C6 . 1.390(8) yes C1 . H11 . 0.932 no C2 . C3 . 1.403(8) yes C2 . C46 . 1.485(8) yes C3 . C4 . 1.370(8) yes C3 . H31 . 0.937 no C4 . C5 . 1.378(8) yes C4 . C7 . 1.556(8) yes C5 . C6 . 1.393(7) yes C5 . H51 . 0.946 no C6 . C11 . 1.490(7) yes C7 . C8 . 1.520(9) yes C7 . C9 . 1.496(9) yes C7 . C10 . 1.548(11) yes C8 . H83 . 0.964 no C8 . H82 . 0.963 no C8 . H81 . 0.973 no C9 . H93 . 0.970 no C9 . H92 . 0.974 no C9 . H91 . 0.974 no C10 . H101 . 0.957 no C10 . H102 . 0.971 no C10 . H103 . 0.972 no C11 . O12 . 1.229(6) yes C11 . N13 . 1.338(7) yes N13 . C14 . 1.445(7) yes N13 . H131 . 0.864 no C14 . C15 . 1.509(8) yes C14 . H142 . 0.984 no C14 . H141 . 0.965 no C15 . O16 . 1.422(6) yes C15 . H152 . 0.983 no C15 . H151 . 0.979 no O16 . C17 . 1.361(6) yes C17 . C18 . 1.397(8) yes C17 . C22 . 1.386(7) yes C18 . C19 . 1.391(7) yes C18 . H181 . 0.956 no C19 . C20 . 1.387(7) yes C19 . H191 . 0.932 no C20 . C21 . 1.396(8) yes C20 . O23 . 1.388(6) yes C21 . C22 . 1.372(7) yes C21 . H211 . 0.931 no C22 . H221 . 0.937 no O23 . C24 . 1.435(7) yes C24 . C25 . 1.486(7) yes C24 . H241 . 0.969 no C24 . H242 . 0.974 no C25 . O26 . 1.412(7) yes C25 . H251 . 0.974 no C25 . H252 . 0.982 no O26 . C27 . 1.425(6) yes C27 . C28 . 1.507(9) yes C27 . H271 . 0.970 no C27 . H272 . 0.974 no C28 . O29 . 1.424(7) yes C28 . H281 . 0.974 no C28 . H282 . 0.981 no O29 . C30 . 1.419(6) yes C30 . C31 . 1.494(8) yes C30 . H302 . 0.968 no C30 . H301 . 0.977 no C31 . O32 . 1.421(6) yes C31 . H312 . 0.972 no C31 . H311 . 0.964 no O32 . C33 . 1.420(6) yes C33 . C34 . 1.493(8) yes C33 . H331 . 0.974 no C33 . H332 . 0.978 no C34 . O35 . 1.439(7) yes C34 . H342 . 0.979 no C34 . H341 . 0.968 no O35 . C36 . 1.373(6) yes C36 . C37 . 1.399(7) yes C36 . C41 . 1.374(8) yes C37 . C38 . 1.375(7) yes C37 . H371 . 0.937 no C38 . C39 . 1.402(7) yes C38 . H381 . 0.940 no C39 . C40 . 1.383(7) yes C39 . O42 . 1.371(6) yes C40 . C41 . 1.389(7) yes C40 . H401 . 0.924 no C41 . H411 . 0.927 no O42 . C43 . 1.431(7) yes C43 . C44 . 1.493(8) yes C43 . H431 . 0.963 no C43 . H432 . 0.973 no C44 . N45 . 1.476(7) yes C44 . H441 . 0.970 no C44 . H442 . 0.965 no N45 . C46 . 1.328(7) yes N45 . H451 . 0.859 no C46 . O47 . 1.219(7) yes O102 . C101 . 1.430(2) yes O102 . H1021 . 0.850 no O104 . C103 . 1.4300(19) yes O104 . H1041 . 0.850 no C101 . H1011 . 0.950 no C101 . H1012 . 0.950 no C101 . H1013 . 0.950 no C103 . H1031 . 0.950 no C103 . H1032 . 0.950 no C103 . H1033 . 0.950 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 C2 . C1 . C6 . 120.6(5) yes C2 . C1 . H11 . 119.1 no C6 . C1 . H11 . 120.3 no C1 . C2 . C3 . 118.5(5) yes C1 . C2 . C46 . 123.2(5) yes C3 . C2 . C46 . 118.0(5) yes C2 . C3 . C4 . 121.8(5) yes C2 . C3 . H31 . 118.2 no C4 . C3 . H31 . 119.9 no C3 . C4 . C5 . 118.3(5) yes C3 . C4 . C7 . 121.3(5) yes C5 . C4 . C7 . 120.1(5) yes C4 . C5 . C6 . 122.4(5) yes C4 . C5 . H51 . 118.8 no C6 . C5 . H51 . 118.8 no C5 . C6 . C1 . 118.4(5) yes C5 . C6 . C11 . 118.8(5) yes C1 . C6 . C11 . 122.7(4) yes C4 . C7 . C8 . 107.1(5) yes C4 . C7 . C9 . 112.6(5) yes C8 . C7 . C9 . 110.8(6) yes C4 . C7 . C10 . 108.9(5) yes C8 . C7 . C10 . 109.6(6) yes C9 . C7 . C10 . 107.8(6) yes C7 . C8 . H83 . 107.2 no C7 . C8 . H82 . 108.4 no H83 . C8 . H82 . 109.1 no C7 . C8 . H81 . 111.1 no H83 . C8 . H81 . 109.9 no H82 . C8 . H81 . 111.0 no C7 . C9 . H93 . 107.6 no C7 . C9 . H92 . 110.0 no H93 . C9 . H92 . 110.0 no C7 . C9 . H91 . 110.5 no H93 . C9 . H91 . 109.0 no H92 . C9 . H91 . 109.7 no C7 . C10 . H101 . 110.6 no C7 . C10 . H102 . 108.7 no H101 . C10 . H102 . 108.4 no C7 . C10 . H103 . 110.5 no H101 . C10 . H103 . 108.7 no H102 . C10 . H103 . 109.9 no C6 . C11 . O12 . 120.7(5) yes C6 . C11 . N13 . 118.0(5) yes O12 . C11 . N13 . 121.3(5) yes C11 . N13 . C14 . 123.1(5) yes C11 . N13 . H131 . 117.3 no C14 . N13 . H131 . 117.9 no N13 . C14 . C15 . 111.4(5) yes N13 . C14 . H142 . 109.2 no C15 . C14 . H142 . 109.8 no N13 . C14 . H141 . 108.1 no C15 . C14 . H141 . 108.6 no H142 . C14 . H141 . 109.7 no C14 . C15 . O16 . 106.2(5) yes C14 . C15 . H152 . 110.8 no O16 . C15 . H152 . 107.9 no C14 . C15 . H151 . 110.9 no O16 . C15 . H151 . 110.1 no H152 . C15 . H151 . 110.7 no C15 . O16 . C17 . 118.5(4) yes O16 . C17 . C18 . 124.1(5) yes O16 . C17 . C22 . 116.3(5) yes C18 . C17 . C22 . 119.6(5) yes C17 . C18 . C19 . 119.6(4) yes C17 . C18 . H181 . 120.5 no C19 . C18 . H181 . 119.9 no C18 . C19 . C20 . 120.4(5) yes C18 . C19 . H191 . 120.0 no C20 . C19 . H191 . 119.7 no C19 . C20 . C21 . 119.6(5) yes C19 . C20 . O23 . 125.1(5) yes C21 . C20 . O23 . 115.3(4) yes C20 . C21 . C22 . 120.1(5) yes C20 . C21 . H211 . 119.6 no C22 . C21 . H211 . 120.3 no C17 . C22 . C21 . 120.8(5) yes C17 . C22 . H221 . 119.0 no C21 . C22 . H221 . 120.2 no C20 . O23 . C24 . 117.1(4) yes O23 . C24 . C25 . 108.4(4) yes O23 . C24 . H241 . 109.8 no C25 . C24 . H241 . 108.8 no O23 . C24 . H242 . 110.8 no C25 . C24 . H242 . 110.6 no H241 . C24 . H242 . 108.4 no C24 . C25 . O26 . 108.6(4) yes C24 . C25 . H251 . 109.7 no O26 . C25 . H251 . 109.5 no C24 . C25 . H252 . 110.7 no O26 . C25 . H252 . 109.6 no H251 . C25 . H252 . 108.6 no C25 . O26 . C27 . 112.9(4) yes O26 . C27 . C28 . 110.1(5) yes O26 . C27 . H271 . 108.7 no C28 . C27 . H271 . 109.8 no O26 . C27 . H272 . 109.2 no C28 . C27 . H272 . 109.8 no H271 . C27 . H272 . 109.2 no C27 . C28 . O29 . 113.6(5) yes C27 . C28 . H281 . 108.4 no O29 . C28 . H281 . 107.8 no C27 . C28 . H282 . 108.9 no O29 . C28 . H282 . 108.6 no H281 . C28 . H282 . 109.4 no C28 . O29 . C30 . 113.7(4) yes O29 . C30 . C31 . 107.3(4) yes O29 . C30 . H302 . 109.1 no C31 . C30 . H302 . 110.1 no O29 . C30 . H301 . 109.6 no C31 . C30 . H301 . 110.7 no H302 . C30 . H301 . 109.9 no C30 . C31 . O32 . 107.9(4) yes C30 . C31 . H312 . 110.2 no O32 . C31 . H312 . 109.4 no C30 . C31 . H311 . 110.6 no O32 . C31 . H311 . 110.8 no H312 . C31 . H311 . 108.0 no C31 . O32 . C33 . 111.9(4) yes O32 . C33 . C34 . 109.4(4) yes O32 . C33 . H331 . 109.9 no C34 . C33 . H331 . 109.6 no O32 . C33 . H332 . 109.0 no C34 . C33 . H332 . 109.4 no H331 . C33 . H332 . 109.5 no C33 . C34 . O35 . 108.6(5) yes C33 . C34 . H342 . 109.3 no O35 . C34 . H342 . 109.4 no C33 . C34 . H341 . 110.4 no O35 . C34 . H341 . 109.7 no H342 . C34 . H341 . 109.4 no C34 . O35 . C36 . 116.6(4) yes O35 . C36 . C37 . 114.9(5) yes O35 . C36 . C41 . 125.6(4) yes C37 . C36 . C41 . 119.4(5) yes C36 . C37 . C38 . 120.6(5) yes C36 . C37 . H371 . 119.6 no C38 . C37 . H371 . 119.8 no C37 . C38 . C39 . 120.1(4) yes C37 . C38 . H381 . 120.4 no C39 . C38 . H381 . 119.5 no C38 . C39 . C40 . 118.8(5) yes C38 . C39 . O42 . 115.4(4) yes C40 . C39 . O42 . 125.8(5) yes C39 . C40 . C41 . 120.9(5) yes C39 . C40 . H401 . 119.6 no C41 . C40 . H401 . 119.5 no C40 . C41 . C36 . 120.1(5) yes C40 . C41 . H411 . 120.0 no C36 . C41 . H411 . 119.9 no C39 . O42 . C43 . 117.9(4) yes O42 . C43 . C44 . 107.3(4) yes O42 . C43 . H431 . 110.6 no C44 . C43 . H431 . 108.8 no O42 . C43 . H432 . 109.6 no C44 . C43 . H432 . 110.9 no H431 . C43 . H432 . 109.6 no C43 . C44 . N45 . 109.5(4) yes C43 . C44 . H441 . 109.2 no N45 . C44 . H441 . 109.3 no C43 . C44 . H442 . 109.6 no N45 . C44 . H442 . 110.7 no H441 . C44 . H442 . 108.5 no C44 . N45 . C46 . 121.9(5) yes C44 . N45 . H451 . 118.4 no C46 . N45 . H451 . 118.7 no C2 . C46 . N45 . 116.2(5) yes C2 . C46 . O47 . 122.2(5) yes N45 . C46 . O47 . 121.6(6) yes C101 . O102 . H1021 . 115.1 no C103 . O104 . H1041 . 116.3 no O102 . C101 . H1011 . 107.1 no O102 . C101 . H1012 . 111.6 no H1011 . C101 . H1012 . 109.5 no O102 . C101 . H1013 . 109.6 no H1011 . C101 . H1013 . 109.5 no H1012 . C101 . H1013 . 109.5 no O104 . C103 . H1031 . 116.3 no O104 . C103 . H1032 . 107.7 no H1031 . C103 . H1032 . 109.5 no O104 . C103 . H1033 . 104.1 no H1031 . C103 . H1033 . 109.5 no H1032 . C103 . H1033 . 109.5 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 . O23 2_556 167 0.93 2.58 3.498(11) yes C24 . H242 . O12 2_656 134 0.97 2.43 3.179(11) yes C43 . H431 . O12 1_465 157 0.96 2.45 3.358(11) yes N13 . H131 . O23 2_556 152 0.86 2.26 3.052(11) yes N13 . H131 . O26 2_556 127 0.86 2.53 3.133(11) yes O102 . H1021 . O47 . 180 0.85 2.07 2.922(11) yes O102 . H1031 . O104 2_467 159 1.19 1.72 2.864(11) yes C103 . H1031 . O47 . 138 0.95 2.29 3.056(11) yes O102 . H1031 . C103 2_467 152 1.19 2.08 3.177(11) yes O104 2_467 H1033 . O104 . 129 0.86 1.90 2.532(11) yes O104 2_467 H1033 . C101 . 128 0.86 2.29 2.908(11) yes C103 . H1033 . O102 2_467 126 0.95 2.52 3.177(11) yes O104 2_467 H1033 . C103 . 120 0.86 0.95 1.575(11) yes C103 . H1033 . C101 2_467 139 0.95 1.87 2.657(11) yes O104 . H1041 . O47 2_467 158 0.85 1.67 2.484(11) yes _chemical_name_common . #===END #============================================================================== data_DCM _database_code_depnum_ccdc_archive 'CCDC 815171' #TrackingRef '- crystallographicdata.cif' #============================================================================== _audit_creation_date 11-01-20 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 023CJS09 _chemical_name_systematic . _chemical_melting_point . _cell_length_a 8.84420(10) _cell_length_b 18.9677(2) _cell_length_c 23.0861(3) _cell_angle_alpha 108.7629(4) _cell_angle_beta 90.3014(4) _cell_angle_gamma 102.0591(5) _cell_volume 3575.06(7) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol 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' _cell_formula_units_Z 4 # Given Formula = C36.50 Cl0.50 N2.50 O9 # Dc = 1.18 Fooo = 1476.00 Mu = 1.23 M = 1270.28 # Found Formula = C36.50 H47 Cl1 N2 O9 # Dc = 1.29 FOOO = 1476.00 Mu = 1.63 M = 1386.47 _chemical_formula_sum 'C36.50 H47 Cl1 N2 O9' _chemical_formula_moiety '2(C36 H46 N2 O9), 0.5(C H2 Cl2)' _chemical_compound_source ? _chemical_formula_weight 693.23 _cell_measurement_reflns_used 15895 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_max 0.900 _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1476 _exptl_absorpt_coefficient_mu 0.163 # Sheldrick geometric approximatio 0.96 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 85693 _reflns_number_total 16246 _diffrn_reflns_av_R_equivalents 0.053 # Number of reflections without Friedels Law is 31828 # Number of reflections with Friedels Law is 16246 # Theoretical number of reflections is about 13986 _diffrn_reflns_theta_min 5.116 _diffrn_reflns_theta_max 27.488 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.939 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -24 _reflns_limit_k_max 23 _reflns_limit_l_min 0 _reflns_limit_l_max 29 _oxford_diffrn_Wilson_B_factor 2.93 _oxford_diffrn_Wilson_scale 5.71 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.70 _refine_diff_density_max 1.49 # 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 13862 _refine_ls_number_restraints 36 _refine_ls_number_parameters 884 _oxford_refine_ls_R_factor_ref 0.1255 _refine_ls_wR_factor_ref 0.2828 _refine_ls_goodness_of_fit_ref 0.9709 _refine_ls_shift/su_max 0.0002657 _refine_ls_shift/su_mean 0.0000263 # The values computed from all data _oxford_reflns_number_all 13864 _refine_ls_R_factor_all 0.1256 _refine_ls_wR_factor_all 0.2828 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 8889 _refine_ls_R_factor_gt 0.0885 _refine_ls_wR_factor_gt 0.2320 # 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: 57.2 87.7 41.8 9.93 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. 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 C1 C 0.6350(4) 0.55704(19) 0.19686(15) 0.0296 1.0000 Uani . . . . . . . C2 C 0.6160(4) 0.4857(2) 0.15213(16) 0.0321 1.0000 Uani . . . . . . . C3 C 0.4898(4) 0.4579(2) 0.10863(17) 0.0381 1.0000 Uani . . . . . . . C4 C 0.3759(4) 0.4989(2) 0.11018(17) 0.0385 1.0000 Uani . . . . . . . C5 C 0.3951(4) 0.5702(2) 0.15656(15) 0.0337 1.0000 Uani . . . . . . . C6 C 0.5232(4) 0.59984(19) 0.19958(15) 0.0290 1.0000 Uani . . . . . . . C7 C 0.2326(5) 0.4641(3) 0.0637(2) 0.0535 1.0000 Uani . . . . . . . C8 C 0.1670(6) 0.3806(3) 0.0577(3) 0.0781 1.0000 Uani . . . . . . . C9 C 0.2803(6) 0.4668(4) 0.0009(2) 0.0714 1.0000 Uani . . . . . . . C10 C 0.1012(6) 0.5051(3) 0.0829(2) 0.0702 1.0000 Uani . . . . . . . C11 C 0.5289(4) 0.67457(19) 0.24970(16) 0.0302 1.0000 Uani . . . . . . . O12 O 0.4242(3) 0.70852(17) 0.25339(15) 0.0561 1.0000 Uani . . . . . . . N13 N 0.6512(3) 0.70089(17) 0.29095(13) 0.0337 1.0000 Uani . . . . . . . C14 C 0.6720(4) 0.77127(19) 0.34271(15) 0.0320 1.0000 Uani . . . . . . . C15 C 0.5995(4) 0.75765(19) 0.39820(15) 0.0329 1.0000 Uani . . . . . . . O16 O 0.6450(3) 0.82791(13) 0.44729(11) 0.0341 1.0000 Uani . . . . . . . C17 C 0.6117(4) 0.82762(18) 0.50532(15) 0.0283 1.0000 Uani . . . . . . . C18 C 0.5107(4) 0.76977(19) 0.51876(16) 0.0329 1.0000 Uani . . . . . . . C19 C 0.4821(4) 0.77668(19) 0.57930(16) 0.0311 1.0000 Uani . . . . . . . C20 C 0.5579(4) 0.84040(18) 0.62678(15) 0.0280 1.0000 Uani . . . . . . . C21 C 0.6599(4) 0.89850(19) 0.61297(16) 0.0315 1.0000 Uani . . . . . . . C22 C 0.6866(4) 0.89265(18) 0.55344(16) 0.0308 1.0000 Uani . . . . . . . O23 O 0.5435(3) 0.85098(13) 0.68813(10) 0.0319 1.0000 Uani . . . . . . . C24 C 0.4201(4) 0.7996(2) 0.70398(16) 0.0353 1.0000 Uani . . . . . . . C25 C 0.4370(4) 0.8156(2) 0.77157(17) 0.0398 1.0000 Uani . . . . . . . O26 O 0.5641(3) 0.78633(15) 0.78433(11) 0.0364 1.0000 Uani . . . . . . . C27 C 0.5769(5) 0.7884(3) 0.84652(16) 0.0453 1.0000 Uani . . . . . . . C28 C 0.7000(5) 0.7477(2) 0.85488(17) 0.0424 1.0000 Uani . . . . . . . O29 O 0.6581(4) 0.66745(16) 0.82425(12) 0.0475 1.0000 Uani . . . . . . . C30 C 0.7012(5) 0.6445(2) 0.76308(16) 0.0366 1.0000 Uani . . . . . . . C31 C 0.6756(5) 0.5584(2) 0.74026(18) 0.0447 1.0000 Uani . . . . . . . O32 O 0.7247(3) 0.53685(13) 0.68035(11) 0.0333 1.0000 Uani . . . . . . . C33 C 0.7146(5) 0.4566(2) 0.65576(17) 0.0415 1.0000 Uani . . . . . . . C34 C 0.7697(4) 0.4372(2) 0.59216(16) 0.0367 1.0000 Uani . . . . . . . O35 O 0.6499(3) 0.43809(14) 0.55087(11) 0.0346 1.0000 Uani . . . . . . . C36 C 0.6820(4) 0.42591(18) 0.49087(15) 0.0291 1.0000 Uani . . . . . . . C37 C 0.5600(4) 0.42397(18) 0.45111(16) 0.0300 1.0000 Uani . . . . . . . C38 C 0.5803(4) 0.41394(18) 0.39021(16) 0.0295 1.0000 Uani . . . . . . . C39 C 0.7225(4) 0.40321(18) 0.36678(16) 0.0307 1.0000 Uani . . . . . . . C40 C 0.8427(4) 0.40329(19) 0.40555(16) 0.0311 1.0000 Uani . . . . . . . C41 C 0.8229(4) 0.41520(18) 0.46784(16) 0.0309 1.0000 Uani . . . . . . . O42 O 0.7292(3) 0.39203(15) 0.30516(11) 0.0365 1.0000 Uani . . . . . . . C43 C 0.8770(4) 0.3912(2) 0.28024(18) 0.0397 1.0000 Uani . . . . . . . C44 C 0.8532(5) 0.3784(3) 0.21284(19) 0.0505 1.0000 Uani . . . . . . . N45 N 0.7781(4) 0.4376(2) 0.20489(16) 0.0498 1.0000 Uani . . . . . . . C46 C 0.7227(5) 0.4336(2) 0.15119(18) 0.0399 1.0000 Uani . . . . . . . O47 O 0.7527(5) 0.3889(2) 0.10272(15) 0.0697 1.0000 Uani . . . . . . . C101 C 0.8619(4) 0.93633(19) 0.79505(15) 0.0303 1.0000 Uani . . . . . . . C102 C 0.8796(4) 1.00454(19) 0.84278(15) 0.0315 1.0000 Uani . . . . . . . C103 C 1.0004(4) 1.0254(2) 0.88868(16) 0.0396 1.0000 Uani . . . . . . . C104 C 1.1052(4) 0.9797(2) 0.88706(16) 0.0411 1.0000 Uani . . . . . . . C105 C 1.0860(4) 0.9119(2) 0.83747(16) 0.0352 1.0000 Uani . . . . . . . C106 C 0.9655(4) 0.88934(19) 0.79204(14) 0.0284 1.0000 Uani . . . . . . . C107 C 1.2452(5) 1.0037(3) 0.9341(2) 0.0599 1.0000 Uani . . . . . . . C108 C 1.3875(6) 1.0300(4) 0.9036(2) 0.0876 1.0000 Uani . . . . . . . C109 C 1.2245(6) 1.0648(4) 0.9919(2) 0.0810 1.0000 Uani . . . . . . . C110 C 1.2647(9) 0.9338(4) 0.9517(3) 0.0991 1.0000 Uani . . . . . . . C111 C 0.9603(4) 0.81725(18) 0.73943(15) 0.0279 1.0000 Uani . . . . . . . O112 O 1.0664(3) 0.78355(16) 0.73272(14) 0.0485 1.0000 Uani . . . . . . . N113 N 0.8364(3) 0.79254(16) 0.69905(13) 0.0310 1.0000 Uani . . . . . . . C114 C 0.8154(4) 0.72291(18) 0.64624(15) 0.0318 1.0000 Uani . . . . . . . C115 C 0.8947(4) 0.73820(18) 0.59233(15) 0.0322 1.0000 Uani . . . . . . . O116 O 0.8518(3) 0.66804(13) 0.54265(11) 0.0348 1.0000 Uani . . . . . . . C117 C 0.8857(4) 0.66902(18) 0.48501(15) 0.0288 1.0000 Uani . . . . . . . C118 C 0.9883(4) 0.72716(18) 0.47289(16) 0.0329 1.0000 Uani . . . . . . . C119 C 1.0166(4) 0.72196(18) 0.41199(16) 0.0313 1.0000 Uani . . . . . . . C120 C 0.9399(4) 0.65899(17) 0.36409(15) 0.0271 1.0000 Uani . . . . . . . C121 C 0.8376(4) 0.60014(18) 0.37697(16) 0.0327 1.0000 Uani . . . . . . . C122 C 0.8114(4) 0.60504(18) 0.43672(16) 0.0314 1.0000 Uani . . . . . . . O123 O 0.9524(3) 0.65003(13) 0.30313(11) 0.0335 1.0000 Uani . . . . . . . C124 C 1.0765(4) 0.7020(2) 0.28774(17) 0.0363 1.0000 Uani . . . . . . . C125 C 1.0581(5) 0.6874(2) 0.22012(17) 0.0411 1.0000 Uani . . . . . . . O126 O 0.9325(3) 0.71827(15) 0.20855(11) 0.0383 1.0000 Uani . . . . . . . C127 C 0.9209(5) 0.7197(3) 0.14728(17) 0.0464 1.0000 Uani . . . . . . . C128 C 0.7962(5) 0.7591(2) 0.13981(18) 0.0467 1.0000 Uani . . . . . . . O129 O 0.8335(4) 0.83913(17) 0.17168(12) 0.0522 1.0000 Uani . . . . . . . C130 C 0.7962(5) 0.8600(2) 0.23325(16) 0.0398 1.0000 Uani . . . . . . . C131 C 0.8218(6) 0.9455(2) 0.25818(18) 0.0468 1.0000 Uani . . . . . . . O132 O 0.7773(3) 0.96615(13) 0.31896(11) 0.0347 1.0000 Uani . . . . . . . C133 C 0.7905(5) 1.0463(2) 0.34523(17) 0.0419 1.0000 Uani . . . . . . . C134 C 0.7360(5) 1.0648(2) 0.40857(17) 0.0383 1.0000 Uani . . . . . . . O135 O 0.8554(3) 1.06384(14) 0.44968(11) 0.0351 1.0000 Uani . . . . . . . C136 C 0.8225(4) 1.07530(18) 0.50980(15) 0.0299 1.0000 Uani . . . . . . . C137 C 0.9439(4) 1.07650(18) 0.54940(16) 0.0311 1.0000 Uani . . . . . . . C138 C 0.9214(4) 1.08535(18) 0.60981(16) 0.0306 1.0000 Uani . . . . . . . C139 C 0.7784(4) 1.09538(18) 0.63321(15) 0.0302 1.0000 Uani . . . . . . . C140 C 0.6591(4) 1.09601(19) 0.59464(16) 0.0311 1.0000 Uani . . . . . . . C141 C 0.6808(4) 1.08539(19) 0.53244(16) 0.0321 1.0000 Uani . . . . . . . O142 O 0.7706(3) 1.10422(14) 0.69453(11) 0.0364 1.0000 Uani . . . . . . . C143 C 0.6243(5) 1.1084(2) 0.71968(18) 0.0412 1.0000 Uani . . . . . . . C144 C 0.6471(6) 1.1182(2) 0.78658(19) 0.0475 1.0000 Uani . . . . . . . N145 N 0.7136(4) 1.05597(19) 0.79307(15) 0.0468 1.0000 Uani . . . . . . . C146 C 0.7842(4) 1.0621(2) 0.84576(17) 0.0376 1.0000 Uani . . . . . . . O147 O 0.7751(5) 1.1123(2) 0.89358(15) 0.0671 1.0000 Uani . . . . . . . C301 C 0.6527(6) 0.2657(5) -0.0251(4) 0.1554 0.801(3) Uani D U P . 1 . . Cl302 Cl 0.6421(5) 0.3014(2) -0.0806(2) 0.1732 0.801(3) Uani D U P . 1 . . Cl303 Cl 0.4871(6) 0.2419(3) 0.00242(18) 0.1958 0.801(3) Uani D U P . 1 . . C304 C 0.851(2) 0.2325(17) 0.0362(11) 0.1554 0.199(3) Uani D U P . 2 . . Cl305 Cl 0.661(2) 0.2196(8) 0.0161(8) 0.1732 0.199(3) Uani D U P . 2 . . Cl306 Cl 0.887(2) 0.2089(10) 0.0985(7) 0.1958 0.199(3) Uani D U P . 2 . . H1011 H 0.7791 0.9213 0.7637 0.0367 1.0000 Uiso R . . . . . . H1031 H 1.0107 1.0734 0.9210 0.0483 1.0000 Uiso R . . . . . . H1051 H 1.1577 0.8799 0.8357 0.0438 1.0000 Uiso R . . . . . . H1093 H 1.3095 1.0731 1.0215 0.1410 1.0000 Uiso R . . . . . . H1092 H 1.2262 1.1116 0.9802 0.1414 1.0000 Uiso R . . . . . . H1091 H 1.1256 1.0477 1.0081 0.1410 1.0000 Uiso R . . . . . . H1103 H 1.3478 0.9511 0.9841 0.1563 1.0000 Uiso R . . . . . . H1102 H 1.1655 0.9158 0.9668 0.1566 1.0000 Uiso R . . . . . . H1101 H 1.2940 0.8959 0.9151 0.1564 1.0000 Uiso R . . . . . . H1083 H 1.4777 1.0373 0.9314 0.1280 1.0000 Uiso R . . . . . . H1082 H 1.3751 1.0797 0.9002 0.1286 1.0000 Uiso R . . . . . . H1081 H 1.3908 0.9911 0.8648 0.1282 1.0000 Uiso R . . . . . . H1142 H 0.8583 0.6849 0.6574 0.0397 1.0000 Uiso R . . . . . . H1141 H 0.7033 0.7033 0.6350 0.0399 1.0000 Uiso R . . . . . . H1151 H 1.0076 0.7534 0.6009 0.0419 1.0000 Uiso R . . . . . . H1152 H 0.8561 0.7775 0.5814 0.0418 1.0000 Uiso R . . . . . . H1181 H 1.0407 0.7708 0.5055 0.0404 1.0000 Uiso R . . . . . . H1191 H 1.0882 0.7610 0.4029 0.0393 1.0000 Uiso R . . . . . . H1211 H 0.7871 0.5553 0.3449 0.0390 1.0000 Uiso R . . . . . . H1221 H 0.7419 0.5652 0.4454 0.0392 1.0000 Uiso R . . . . . . H1241 H 1.0697 0.7542 0.3107 0.0472 1.0000 Uiso R . . . . . . H1242 H 1.1745 0.6926 0.2993 0.0475 1.0000 Uiso R . . . . . . H1251 H 1.1541 0.7128 0.2058 0.0502 1.0000 Uiso R . . . . . . H1252 H 1.0375 0.6333 0.1974 0.0498 1.0000 Uiso R . . . . . . H1272 H 1.0215 0.7468 0.1382 0.0596 1.0000 Uiso R . . . . . . H1271 H 0.8943 0.6655 0.1191 0.0595 1.0000 Uiso R . . . . . . H1281 H 0.7797 0.7522 0.0961 0.0581 1.0000 Uiso R . . . . . . H1282 H 0.7000 0.7362 0.1545 0.0579 1.0000 Uiso R . . . . . . H1301 H 0.8615 0.8431 0.2582 0.0512 1.0000 Uiso R . . . . . . H1302 H 0.6839 0.8385 0.2347 0.0514 1.0000 Uiso R . . . . . . H1312 H 0.9322 0.9693 0.2588 0.0595 1.0000 Uiso R . . . . . . H1311 H 0.7586 0.9636 0.2335 0.0593 1.0000 Uiso R . . . . . . H1331 H 0.9002 1.0729 0.3475 0.0545 1.0000 Uiso R . . . . . . H1332 H 0.7277 1.0621 0.3186 0.0544 1.0000 Uiso R . . . . . . H1341 H 0.7150 1.1155 0.4217 0.0481 1.0000 Uiso R . . . . . . H1342 H 0.6417 1.0276 0.4089 0.0478 1.0000 Uiso R . . . . . . H1411 H 0.5974 1.0848 0.5060 0.0390 1.0000 Uiso R . . . . . . H1401 H 0.5624 1.1036 0.6103 0.0378 1.0000 Uiso R . . . . . . H1381 H 1.0036 1.0841 0.6361 0.0380 1.0000 Uiso R . . . . . . H1371 H 1.0413 1.0715 0.5340 0.0370 1.0000 Uiso R . . . . . . H1431 H 0.5862 1.1511 0.7147 0.0510 1.0000 Uiso R . . . . . . H1432 H 0.5485 1.0595 0.6980 0.0502 1.0000 Uiso R . . . . . . H1442 H 0.7151 1.1692 0.8079 0.0606 1.0000 Uiso R . . . . . . H1441 H 0.5451 1.1166 0.8044 0.0616 1.0000 Uiso R . . . . . . H11 H 0.7192 0.5761 0.2262 0.0363 1.0000 Uiso R . . . . . . H51 H 0.3199 0.6010 0.1599 0.0424 1.0000 Uiso R . . . . . . H31 H 0.4822 0.4092 0.0773 0.0474 1.0000 Uiso R . . . . . . H91 H 0.1875 0.4422 -0.0277 0.1139 1.0000 Uiso R . . . . . . H93 H 0.3178 0.5227 0.0060 0.1146 1.0000 Uiso R . . . . . . H92 H 0.3588 0.4366 -0.0099 0.1138 1.0000 Uiso R . . . . . . H81 H 0.0722 0.3628 0.0294 0.1320 1.0000 Uiso R . . . . . . H83 H 0.1439 0.3792 0.1000 0.1326 1.0000 Uiso R . . . . . . H82 H 0.2489 0.3529 0.0396 0.1325 1.0000 Uiso R . . . . . . H101 H 0.0140 0.4774 0.0520 0.1119 1.0000 Uiso R . . . . . . H103 H 0.1415 0.5589 0.0823 0.1121 1.0000 Uiso R . . . . . . H102 H 0.0776 0.5011 0.1247 0.1122 1.0000 Uiso R . . . . . . H441 H 0.9537 0.3811 0.1946 0.0695 1.0000 Uiso R . . . . . . H442 H 0.7844 0.3285 0.1920 0.0684 1.0000 Uiso R . . . . . . H432 H 0.9485 0.4417 0.3009 0.0487 1.0000 Uiso R . . . . . . H431 H 0.9201 0.3508 0.2879 0.0490 1.0000 Uiso R . . . . . . H381 H 0.4973 0.4146 0.3636 0.0357 1.0000 Uiso R . . . . . . H371 H 0.4629 0.4302 0.4668 0.0359 1.0000 Uiso R . . . . . . H411 H 0.9067 0.4163 0.4942 0.0382 1.0000 Uiso R . . . . . . H401 H 0.9389 0.3956 0.3893 0.0389 1.0000 Uiso R . . . . . . H342 H 0.8640 0.4741 0.5908 0.0471 1.0000 Uiso R . . . . . . H341 H 0.7922 0.3864 0.5803 0.0478 1.0000 Uiso R . . . . . . H332 H 0.7815 0.4417 0.6814 0.0522 1.0000 Uiso R . . . . . . H331 H 0.6072 0.4292 0.6545 0.0523 1.0000 Uiso R . . . . . . H311 H 0.7372 0.5423 0.7669 0.0572 1.0000 Uiso R . . . . . . H312 H 0.5651 0.5342 0.7399 0.0573 1.0000 Uiso R . . . . . . H302 H 0.8122 0.6662 0.7624 0.0492 1.0000 Uiso R . . . . . . H301 H 0.6368 0.6616 0.7367 0.0487 1.0000 Uiso R . . . . . . H282 H 0.7150 0.7551 0.8997 0.0542 1.0000 Uiso R . . . . . . H281 H 0.8009 0.7712 0.8420 0.0541 1.0000 Uiso R . . . . . . H271 H 0.6058 0.8425 0.8739 0.0560 1.0000 Uiso R . . . . . . H272 H 0.4756 0.7642 0.8587 0.0566 1.0000 Uiso R . . . . . . H252 H 0.4563 0.8699 0.7930 0.0512 1.0000 Uiso R . . . . . . H251 H 0.3420 0.7896 0.7841 0.0514 1.0000 Uiso R . . . . . . H242 H 0.3205 0.8083 0.6926 0.0474 1.0000 Uiso R . . . . . . H241 H 0.4267 0.7465 0.6834 0.0470 1.0000 Uiso R . . . . . . H211 H 0.7106 0.9422 0.6456 0.0382 1.0000 Uiso R . . . . . . H221 H 0.7547 0.9319 0.5443 0.0392 1.0000 Uiso R . . . . . . H181 H 0.4591 0.7260 0.4871 0.0409 1.0000 Uiso R . . . . . . H191 H 0.4103 0.7372 0.5876 0.0394 1.0000 Uiso R . . . . . . H152 H 0.4866 0.7422 0.3909 0.0409 1.0000 Uiso R . . . . . . H151 H 0.6391 0.7189 0.4074 0.0412 1.0000 Uiso R . . . . . . H141 H 0.7844 0.7929 0.3540 0.0410 1.0000 Uiso R . . . . . . H142 H 0.6260 0.8081 0.3315 0.0410 1.0000 Uiso R . . . . . . H131 H 0.7305 0.6790 0.2840 0.0435 1.0000 Uiso R . . . . . . H1131 H 0.7548 0.8126 0.7087 0.0410 1.0000 Uiso R . . . . . . H451 H 0.7722 0.4755 0.2361 0.0658 1.0000 Uiso R . . . . . . H1451 H 0.7060 1.0154 0.7626 0.0588 1.0000 Uiso R . . . . . . H3011 H 0.7201 0.3026 0.0078 0.2177 0.801(3) Uiso R . P . 1 . . H3012 H 0.6941 0.2214 -0.0401 0.2177 0.801(3) Uiso R . P . 1 . . H3042 H 0.9043 0.2837 0.0429 0.2177 0.199(3) Uiso R . P . 2 . . H3041 H 0.8874 0.1994 0.0017 0.2177 0.199(3) Uiso R . P . 2 . . 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 0.0302(17) 0.0342(17) 0.0287(16) 0.0141(14) 0.0018(13) 0.0103(14) C2 0.0321(18) 0.0322(17) 0.0359(18) 0.0141(14) 0.0105(14) 0.0107(14) C3 0.040(2) 0.0354(18) 0.0336(18) 0.0039(15) 0.0052(15) 0.0075(15) C4 0.038(2) 0.044(2) 0.0330(18) 0.0103(15) 0.0012(15) 0.0118(16) C5 0.0324(18) 0.0401(19) 0.0307(17) 0.0115(14) 0.0001(13) 0.0129(15) C6 0.0279(17) 0.0309(16) 0.0310(16) 0.0132(13) 0.0031(13) 0.0081(13) C7 0.050(2) 0.056(3) 0.043(2) -0.0013(19) -0.0090(19) 0.016(2) C8 0.056(3) 0.064(3) 0.093(4) 0.012(3) -0.030(3) -0.007(2) C9 0.064(3) 0.091(4) 0.046(3) 0.005(3) -0.017(2) 0.016(3) C10 0.045(3) 0.079(4) 0.065(3) -0.003(3) -0.019(2) 0.012(2) C11 0.0267(16) 0.0314(17) 0.0359(17) 0.0134(14) 0.0041(13) 0.0102(13) O12 0.0381(16) 0.0440(16) 0.072(2) -0.0085(14) -0.0166(14) 0.0224(13) N13 0.0343(16) 0.0343(15) 0.0318(15) 0.0052(12) -0.0003(12) 0.0155(12) C14 0.0333(18) 0.0294(17) 0.0318(17) 0.0057(14) 0.0024(13) 0.0109(14) C15 0.0363(18) 0.0282(17) 0.0309(17) 0.0040(13) -0.0021(14) 0.0089(14) O16 0.0457(14) 0.0234(11) 0.0294(12) 0.0055(9) 0.0015(10) 0.0048(10) C17 0.0292(17) 0.0248(15) 0.0323(17) 0.0083(13) -0.0004(13) 0.0107(13) C18 0.0378(19) 0.0244(16) 0.0320(17) 0.0050(13) -0.0034(14) 0.0041(14) C19 0.0327(17) 0.0255(16) 0.0343(17) 0.0101(13) -0.0008(13) 0.0044(13) C20 0.0286(16) 0.0257(15) 0.0297(16) 0.0064(13) -0.0011(13) 0.0105(13) C21 0.0324(17) 0.0251(16) 0.0331(17) 0.0043(13) -0.0025(13) 0.0063(13) C22 0.0306(17) 0.0230(15) 0.0377(18) 0.0092(13) -0.0006(13) 0.0048(13) O23 0.0353(13) 0.0269(12) 0.0302(12) 0.0059(9) -0.0007(9) 0.0052(10) C24 0.0293(17) 0.0393(19) 0.0388(19) 0.0142(15) 0.0006(14) 0.0089(14) C25 0.037(2) 0.048(2) 0.0373(19) 0.0131(16) 0.0087(15) 0.0184(17) O26 0.0375(13) 0.0455(14) 0.0288(12) 0.0125(11) 0.0040(10) 0.0146(11) C27 0.055(2) 0.057(2) 0.0245(17) 0.0087(16) 0.0060(16) 0.020(2) C28 0.053(2) 0.040(2) 0.0289(18) 0.0050(15) -0.0049(16) 0.0087(17) O29 0.0687(19) 0.0385(14) 0.0329(14) 0.0114(11) 0.0131(13) 0.0074(13) C30 0.046(2) 0.0346(18) 0.0302(17) 0.0100(14) 0.0073(15) 0.0123(16) C31 0.061(3) 0.036(2) 0.036(2) 0.0127(16) 0.0123(17) 0.0061(18) O32 0.0408(14) 0.0287(12) 0.0312(12) 0.0103(10) 0.0036(10) 0.0088(10) C33 0.057(2) 0.0325(19) 0.038(2) 0.0122(15) 0.0022(17) 0.0142(17) C34 0.042(2) 0.0363(19) 0.0329(18) 0.0082(15) -0.0036(15) 0.0166(16) O35 0.0313(13) 0.0389(13) 0.0327(13) 0.0084(10) 0.0003(10) 0.0112(10) C36 0.0308(17) 0.0218(15) 0.0326(17) 0.0065(13) 0.0013(13) 0.0051(13) C37 0.0270(16) 0.0226(15) 0.0381(18) 0.0059(13) 0.0001(13) 0.0072(12) C38 0.0252(16) 0.0231(15) 0.0384(18) 0.0070(13) -0.0044(13) 0.0063(12) C39 0.0322(18) 0.0248(16) 0.0345(17) 0.0077(13) 0.0016(14) 0.0083(13) C40 0.0268(17) 0.0301(17) 0.0387(18) 0.0114(14) 0.0024(13) 0.0118(13) C41 0.0297(17) 0.0272(16) 0.0358(18) 0.0101(13) -0.0038(13) 0.0071(13) O42 0.0358(13) 0.0453(14) 0.0322(13) 0.0136(11) 0.0031(10) 0.0160(11) C43 0.040(2) 0.046(2) 0.045(2) 0.0202(17) 0.0119(16) 0.0254(17) C44 0.058(3) 0.069(3) 0.041(2) 0.023(2) 0.0137(19) 0.042(2) N45 0.063(2) 0.050(2) 0.0389(18) 0.0063(15) 0.0004(16) 0.0308(18) C46 0.043(2) 0.0367(19) 0.045(2) 0.0140(16) 0.0120(16) 0.0170(16) O47 0.096(3) 0.068(2) 0.0432(17) -0.0009(16) -0.0034(17) 0.046(2) C101 0.0273(16) 0.0322(17) 0.0311(17) 0.0103(13) 0.0005(13) 0.0061(13) C102 0.0352(18) 0.0305(17) 0.0297(16) 0.0094(13) 0.0101(13) 0.0097(14) C103 0.040(2) 0.043(2) 0.0304(18) 0.0063(15) 0.0045(15) 0.0058(16) C104 0.036(2) 0.056(2) 0.0267(17) 0.0090(16) -0.0016(14) 0.0089(17) C105 0.0301(18) 0.046(2) 0.0319(17) 0.0126(15) 0.0004(14) 0.0130(15) C106 0.0294(17) 0.0315(17) 0.0265(16) 0.0109(13) 0.0041(13) 0.0095(13) C107 0.043(2) 0.086(3) 0.040(2) 0.004(2) -0.0077(18) 0.016(2) C108 0.041(3) 0.126(5) 0.057(3) -0.010(3) -0.005(2) 0.001(3) C109 0.057(3) 0.118(5) 0.038(2) -0.010(3) -0.014(2) 0.012(3) C110 0.109(5) 0.110(5) 0.077(4) 0.023(4) -0.048(4) 0.033(4) C111 0.0263(16) 0.0256(15) 0.0340(17) 0.0119(13) 0.0030(13) 0.0072(13) O112 0.0356(15) 0.0402(15) 0.0620(18) -0.0013(13) -0.0081(12) 0.0212(12) N113 0.0280(14) 0.0315(15) 0.0320(14) 0.0035(12) 0.0001(11) 0.0146(11) C114 0.0334(18) 0.0259(16) 0.0348(18) 0.0056(13) 0.0029(14) 0.0109(13) C115 0.0413(19) 0.0238(16) 0.0291(17) 0.0037(13) -0.0007(14) 0.0101(14) O116 0.0458(15) 0.0242(11) 0.0316(12) 0.0072(9) 0.0032(10) 0.0051(10) C117 0.0325(17) 0.0234(15) 0.0306(16) 0.0065(13) -0.0004(13) 0.0105(13) C118 0.0407(19) 0.0231(15) 0.0304(17) 0.0043(13) -0.0052(14) 0.0049(14) C119 0.0361(18) 0.0229(15) 0.0339(17) 0.0090(13) -0.0026(14) 0.0054(13) C120 0.0286(16) 0.0226(15) 0.0310(16) 0.0070(12) -0.0009(12) 0.0106(12) C121 0.0349(18) 0.0217(15) 0.0348(18) 0.0012(13) -0.0044(14) 0.0053(13) C122 0.0349(18) 0.0208(15) 0.0359(18) 0.0070(13) -0.0013(14) 0.0046(13) O123 0.0354(13) 0.0314(12) 0.0298(12) 0.0069(10) -0.0003(10) 0.0043(10) C124 0.0304(18) 0.0402(19) 0.0386(19) 0.0138(16) 0.0029(14) 0.0070(15) C125 0.041(2) 0.048(2) 0.0352(19) 0.0113(16) 0.0086(15) 0.0173(17) O126 0.0405(14) 0.0455(14) 0.0307(13) 0.0107(11) 0.0035(10) 0.0168(11) C127 0.057(3) 0.053(2) 0.0276(18) 0.0086(16) 0.0020(16) 0.017(2) C128 0.058(3) 0.045(2) 0.0319(19) 0.0057(16) -0.0052(17) 0.0116(19) O129 0.080(2) 0.0438(16) 0.0329(14) 0.0128(12) 0.0133(14) 0.0128(15) C130 0.052(2) 0.039(2) 0.0311(18) 0.0110(15) 0.0064(16) 0.0160(17) C131 0.066(3) 0.039(2) 0.037(2) 0.0149(17) 0.0142(18) 0.0109(19) O132 0.0418(14) 0.0313(12) 0.0327(12) 0.0109(10) 0.0047(10) 0.0113(11) C133 0.057(2) 0.0336(19) 0.038(2) 0.0132(15) 0.0010(17) 0.0120(17) C134 0.046(2) 0.0335(18) 0.0366(19) 0.0086(15) -0.0018(16) 0.0167(16) O135 0.0339(13) 0.0382(13) 0.0329(13) 0.0080(10) 0.0005(10) 0.0130(10) C136 0.0306(17) 0.0208(15) 0.0354(17) 0.0052(13) -0.0017(13) 0.0064(13) C137 0.0237(16) 0.0257(16) 0.0415(19) 0.0059(14) 0.0019(13) 0.0086(13) C138 0.0293(17) 0.0237(15) 0.0364(18) 0.0058(13) -0.0052(13) 0.0078(13) C139 0.0310(17) 0.0220(15) 0.0350(17) 0.0056(13) -0.0021(13) 0.0069(13) C140 0.0278(17) 0.0282(16) 0.0391(18) 0.0105(14) 0.0031(13) 0.0110(13) C141 0.0278(17) 0.0277(16) 0.0404(19) 0.0085(14) -0.0042(14) 0.0097(13) O142 0.0362(14) 0.0417(14) 0.0344(13) 0.0131(11) 0.0019(10) 0.0147(11) C143 0.042(2) 0.047(2) 0.043(2) 0.0162(17) 0.0093(16) 0.0243(17) C144 0.064(3) 0.048(2) 0.043(2) 0.0167(18) 0.0135(19) 0.037(2) N145 0.067(2) 0.0390(17) 0.0359(17) 0.0038(14) 0.0007(15) 0.0293(16) C146 0.041(2) 0.0366(19) 0.0358(19) 0.0102(15) 0.0114(15) 0.0131(16) O147 0.089(3) 0.063(2) 0.0447(17) -0.0068(15) -0.0059(16) 0.0450(19) C301 0.219(4) 0.057(5) 0.147(7) -0.003(4) 0.038(5) -0.005(6) Cl302 0.214(4) 0.110(2) 0.197(4) 0.052(2) 0.077(3) 0.038(2) Cl303 0.231(4) 0.172(4) 0.130(3) 0.024(2) 0.032(2) -0.032(3) C304 0.219(4) 0.057(5) 0.147(7) -0.003(4) 0.038(5) -0.005(6) Cl305 0.214(4) 0.110(2) 0.197(4) 0.052(2) 0.077(3) 0.038(2) Cl306 0.231(4) 0.172(4) 0.130(3) 0.024(2) 0.032(2) -0.032(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4489(10) 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 . C2 . 1.389(5) yes C1 . C6 . 1.394(5) yes C1 . H11 . 0.931 no C2 . C3 . 1.391(5) yes C2 . C46 . 1.499(5) yes C3 . C4 . 1.389(5) yes C3 . H31 . 0.961 no C4 . C5 . 1.405(5) yes C4 . C7 . 1.541(5) yes C5 . C6 . 1.396(5) yes C5 . H51 . 0.963 no C6 . C11 . 1.505(5) yes C7 . C8 . 1.529(7) yes C7 . C9 . 1.525(7) yes C7 . C10 . 1.521(7) yes C8 . H81 . 0.989 no C8 . H83 . 1.006 no C8 . H82 . 0.998 no C9 . H91 . 0.981 no C9 . H93 . 1.009 no C9 . H92 . 0.974 no C10 . H101 . 0.982 no C10 . H103 . 1.013 no C10 . H102 . 1.011 no C11 . O12 . 1.222(4) yes C11 . N13 . 1.336(4) yes N13 . C14 . 1.454(4) yes N13 . H131 . 0.876 no C14 . C15 . 1.507(5) yes C14 . H141 . 0.991 no C14 . H142 . 0.977 no C15 . O16 . 1.422(4) yes C15 . H152 . 0.977 no C15 . H151 . 0.957 no O16 . C17 . 1.375(4) yes C17 . C18 . 1.382(5) yes C17 . C22 . 1.401(4) yes C18 . C19 . 1.391(5) yes C18 . H181 . 0.938 no C19 . C20 . 1.383(5) yes C19 . H191 . 0.946 no C20 . C21 . 1.394(5) yes C20 . O23 . 1.375(4) yes C21 . C22 . 1.368(5) yes C21 . H211 . 0.946 no C22 . H221 . 0.936 no O23 . C24 . 1.436(4) yes C24 . C25 . 1.491(5) yes C24 . H242 . 0.979 no C24 . H241 . 0.980 no C25 . O26 . 1.421(4) yes C25 . H252 . 0.966 no C25 . H251 . 0.976 no O26 . C27 . 1.427(4) yes C27 . C28 . 1.505(6) yes C27 . H271 . 0.994 no C27 . H272 . 1.002 no C28 . O29 . 1.422(5) yes C28 . H282 . 1.003 no C28 . H281 . 1.003 no O29 . C30 . 1.417(4) yes C30 . C31 . 1.511(5) yes C30 . H302 . 0.984 no C30 . H301 . 1.001 no C31 . O32 . 1.409(4) yes C31 . H311 . 0.979 no C31 . H312 . 0.988 no O32 . C33 . 1.426(4) yes C33 . C34 . 1.505(5) yes C33 . H332 . 0.977 no C33 . H331 . 0.979 no C34 . O35 . 1.428(4) yes C34 . H342 . 0.979 no C34 . H341 . 0.976 no O35 . C36 . 1.370(4) yes C36 . C37 . 1.399(5) yes C36 . C41 . 1.386(5) yes C37 . C38 . 1.375(5) yes C37 . H371 . 0.949 no C38 . C39 . 1.400(5) yes C38 . H381 . 0.960 no C39 . C40 . 1.386(5) yes C39 . O42 . 1.373(4) yes C40 . C41 . 1.400(5) yes C40 . H401 . 0.952 no C41 . H411 . 0.949 no O42 . C43 . 1.431(4) yes C43 . C44 . 1.502(5) yes C43 . H432 . 0.997 no C43 . H431 . 0.986 no C44 . N45 . 1.477(5) yes C44 . H441 . 0.984 no C44 . H442 . 0.980 no N45 . C46 . 1.304(5) yes N45 . H451 . 0.850 no C46 . O47 . 1.236(5) yes C101 . C102 . 1.382(5) yes C101 . C106 . 1.393(5) yes C101 . H1011 . 0.957 no C102 . C103 . 1.400(5) yes C102 . C146 . 1.500(5) yes C103 . C104 . 1.389(6) yes C103 . H1031 . 0.959 no C104 . C105 . 1.397(5) yes C104 . C107 . 1.533(5) yes C105 . C106 . 1.389(5) yes C105 . H1051 . 0.958 no C106 . C111 . 1.501(4) yes C107 . C108 . 1.517(7) yes C107 . C109 . 1.502(7) yes C107 . C110 . 1.549(8) yes C108 . H1083 . 0.979 no C108 . H1082 . 0.998 no C108 . H1081 . 0.966 no C109 . H1093 . 0.965 no C109 . H1092 . 1.005 no C109 . H1091 . 0.986 no C110 . H1103 . 0.971 no C110 . H1102 . 0.981 no C110 . H1101 . 0.994 no C111 . O112 . 1.225(4) yes C111 . N113 . 1.336(4) yes N113 . C114 . 1.457(4) yes N113 . H1131 . 0.881 no C114 . C115 . 1.511(5) yes C114 . H1142 . 0.982 no C114 . H1141 . 0.985 no C115 . O116 . 1.426(4) yes C115 . H1151 . 0.980 no C115 . H1152 . 0.981 no O116 . C117 . 1.371(4) yes C117 . C118 . 1.379(5) yes C117 . C122 . 1.391(4) yes C118 . C119 . 1.405(5) yes C118 . H1181 . 0.950 no C119 . C120 . 1.383(4) yes C119 . H1191 . 0.949 no C120 . C121 . 1.396(5) yes C120 . O123 . 1.370(4) yes C121 . C122 . 1.377(5) yes C121 . H1211 . 0.951 no C122 . H1221 . 0.946 no O123 . C124 . 1.442(4) yes C124 . C125 . 1.497(5) yes C124 . H1241 . 0.976 no C124 . H1242 . 0.973 no C125 . O126 . 1.420(4) yes C125 . H1251 . 0.998 no C125 . H1252 . 0.967 no O126 . C127 . 1.427(4) yes C127 . C128 . 1.494(6) yes C127 . H1272 . 0.990 no C127 . H1271 . 1.000 no C128 . O129 . 1.422(5) yes C128 . H1281 . 0.981 no C128 . H1282 . 0.986 no O129 . C130 . 1.408(4) yes C130 . C131 . 1.503(5) yes C130 . H1301 . 0.980 no C130 . H1302 . 0.997 no C131 . O132 . 1.412(4) yes C131 . H1312 . 0.984 no C131 . H1311 . 0.979 no O132 . C133 . 1.423(4) yes C133 . C134 . 1.497(5) yes C133 . H1331 . 0.988 no C133 . H1332 . 0.980 no C134 . O135 . 1.423(4) yes C134 . H1341 . 0.970 no C134 . H1342 . 0.975 no O135 . C136 . 1.377(4) yes C136 . C137 . 1.398(5) yes C136 . C141 . 1.387(5) yes C137 . C138 . 1.371(5) yes C137 . H1371 . 0.944 no C138 . C139 . 1.403(5) yes C138 . H1381 . 0.953 no C139 . C140 . 1.382(5) yes C139 . O142 . 1.375(4) yes C140 . C141 . 1.404(5) yes C140 . H1401 . 0.951 no C141 . H1411 . 0.951 no O142 . C143 . 1.428(4) yes C143 . C144 . 1.502(5) yes C143 . H1431 . 0.976 no C143 . H1432 . 0.999 no C144 . N145 . 1.471(5) yes C144 . H1442 . 0.994 no C144 . H1441 . 0.992 no N145 . C146 . 1.324(5) yes N145 . H1451 . 0.850 no C146 . O147 . 1.220(5) yes C301 . Cl302 . 1.642(7) yes C301 . Cl303 . 1.634(7) yes C301 . H3011 . 0.950 no C301 . H3012 . 0.950 no C304 . Cl305 . 1.686(10) yes C304 . Cl306 . 1.686(10) yes C304 . H3042 . 0.950 no C304 . H3041 . 0.950 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 C2 . C1 . C6 . 119.6(3) yes C2 . C1 . H11 . 121.2 no C6 . C1 . H11 . 119.1 no C1 . C2 . C3 . 120.6(3) yes C1 . C2 . C46 . 121.9(3) yes C3 . C2 . C46 . 117.3(3) yes C2 . C3 . C4 . 121.2(3) yes C2 . C3 . H31 . 118.6 no C4 . C3 . H31 . 120.2 no C3 . C4 . C5 . 117.4(3) yes C3 . C4 . C7 . 119.8(3) yes C5 . C4 . C7 . 122.8(3) yes C4 . C5 . C6 . 122.2(3) yes C4 . C5 . H51 . 121.0 no C6 . C5 . H51 . 116.8 no C5 . C6 . C1 . 119.0(3) yes C5 . C6 . C11 . 118.2(3) yes C1 . C6 . C11 . 122.7(3) yes C4 . C7 . C8 . 111.1(4) yes C4 . C7 . C9 . 108.9(4) yes C8 . C7 . C9 . 108.0(4) yes C4 . C7 . C10 . 112.2(3) yes C8 . C7 . C10 . 106.2(4) yes C9 . C7 . C10 . 110.2(4) yes C7 . C8 . H81 . 107.0 no C7 . C8 . H83 . 107.2 no H81 . C8 . H83 . 112.0 no C7 . C8 . H82 . 105.5 no H81 . C8 . H82 . 111.0 no H83 . C8 . H82 . 113.6 no C7 . C9 . H91 . 106.5 no C7 . C9 . H93 . 106.0 no H91 . C9 . H93 . 112.9 no C7 . C9 . H92 . 106.1 no H91 . C9 . H92 . 109.9 no H93 . C9 . H92 . 114.8 no C7 . C10 . H101 . 106.3 no C7 . C10 . H103 . 105.9 no H101 . C10 . H103 . 111.4 no C7 . C10 . H102 . 105.2 no H101 . C10 . H102 . 112.2 no H103 . C10 . H102 . 115.1 no C6 . C11 . O12 . 121.4(3) yes C6 . C11 . N13 . 117.0(3) yes O12 . C11 . N13 . 121.6(3) yes C11 . N13 . C14 . 123.6(3) yes C11 . N13 . H131 . 119.1 no C14 . N13 . H131 . 116.6 no N13 . C14 . C15 . 111.7(3) yes N13 . C14 . H141 . 109.2 no C15 . C14 . H141 . 107.7 no N13 . C14 . H142 . 109.8 no C15 . C14 . H142 . 109.3 no H141 . C14 . H142 . 109.2 no C14 . C15 . O16 . 106.1(3) yes C14 . C15 . H152 . 110.7 no O16 . C15 . H152 . 110.9 no C14 . C15 . H151 . 109.3 no O16 . C15 . H151 . 109.8 no H152 . C15 . H151 . 110.0 no C15 . O16 . C17 . 117.5(3) yes O16 . C17 . C18 . 125.2(3) yes O16 . C17 . C22 . 115.5(3) yes C18 . C17 . C22 . 119.2(3) yes C17 . C18 . C19 . 120.3(3) yes C17 . C18 . H181 . 120.3 no C19 . C18 . H181 . 119.4 no C18 . C19 . C20 . 120.4(3) yes C18 . C19 . H191 . 119.1 no C20 . C19 . H191 . 120.5 no C19 . C20 . C21 . 119.0(3) yes C19 . C20 . O23 . 124.9(3) yes C21 . C20 . O23 . 116.0(3) yes C20 . C21 . C22 . 120.8(3) yes C20 . C21 . H211 . 118.7 no C22 . C21 . H211 . 120.4 no C17 . C22 . C21 . 120.2(3) yes C17 . C22 . H221 . 119.2 no C21 . C22 . H221 . 120.6 no C20 . O23 . C24 . 117.4(3) yes O23 . C24 . C25 . 108.4(3) yes O23 . C24 . H242 . 109.2 no C25 . C24 . H242 . 109.6 no O23 . C24 . H241 . 110.5 no C25 . C24 . H241 . 108.3 no H242 . C24 . H241 . 110.9 no C24 . C25 . O26 . 107.7(3) yes C24 . C25 . H252 . 110.3 no O26 . C25 . H252 . 109.9 no C24 . C25 . H251 . 108.8 no O26 . C25 . H251 . 109.8 no H252 . C25 . H251 . 110.2 no C25 . O26 . C27 . 112.5(3) yes O26 . C27 . C28 . 109.7(3) yes O26 . C27 . H271 . 109.2 no C28 . C27 . H271 . 109.3 no O26 . C27 . H272 . 111.2 no C28 . C27 . H272 . 109.7 no H271 . C27 . H272 . 107.7 no C27 . C28 . O29 . 113.3(3) yes C27 . C28 . H282 . 108.1 no O29 . C28 . H282 . 106.3 no C27 . C28 . H281 . 109.8 no O29 . C28 . H281 . 111.6 no H282 . C28 . H281 . 107.6 no C28 . O29 . C30 . 113.9(3) yes O29 . C30 . C31 . 108.0(3) yes O29 . C30 . H302 . 109.5 no C31 . C30 . H302 . 108.3 no O29 . C30 . H301 . 109.9 no C31 . C30 . H301 . 110.4 no H302 . C30 . H301 . 110.7 no C30 . C31 . O32 . 107.3(3) yes C30 . C31 . H311 . 109.7 no O32 . C31 . H311 . 109.8 no C30 . C31 . H312 . 111.1 no O32 . C31 . H312 . 110.1 no H311 . C31 . H312 . 109.0 no C31 . O32 . C33 . 111.9(3) yes O32 . C33 . C34 . 109.4(3) yes O32 . C33 . H332 . 109.5 no C34 . C33 . H332 . 108.4 no O32 . C33 . H331 . 109.6 no C34 . C33 . H331 . 110.1 no H332 . C33 . H331 . 109.8 no C33 . C34 . O35 . 108.5(3) yes C33 . C34 . H342 . 110.7 no O35 . C34 . H342 . 109.7 no C33 . C34 . H341 . 109.2 no O35 . C34 . H341 . 109.9 no H342 . C34 . H341 . 108.8 no C34 . O35 . C36 . 117.2(3) yes O35 . C36 . C37 . 115.7(3) yes O35 . C36 . C41 . 125.0(3) yes C37 . C36 . C41 . 119.3(3) yes C36 . C37 . C38 . 120.7(3) yes C36 . C37 . H371 . 119.1 no C38 . C37 . H371 . 120.2 no C37 . C38 . C39 . 120.2(3) yes C37 . C38 . H381 . 120.2 no C39 . C38 . H381 . 119.6 no C38 . C39 . C40 . 119.4(3) yes C38 . C39 . O42 . 115.5(3) yes C40 . C39 . O42 . 125.1(3) yes C39 . C40 . C41 . 120.3(3) yes C39 . C40 . H401 . 119.1 no C41 . C40 . H401 . 120.6 no C40 . C41 . C36 . 120.1(3) yes C40 . C41 . H411 . 119.6 no C36 . C41 . H411 . 120.3 no C39 . O42 . C43 . 118.0(3) yes O42 . C43 . C44 . 107.5(3) yes O42 . C43 . H432 . 108.6 no C44 . C43 . H432 . 110.0 no O42 . C43 . H431 . 109.8 no C44 . C43 . H431 . 111.8 no H432 . C43 . H431 . 109.0 no C43 . C44 . N45 . 108.7(3) yes C43 . C44 . H441 . 109.8 no N45 . C44 . H441 . 110.2 no C43 . C44 . H442 . 110.6 no N45 . C44 . H442 . 107.8 no H441 . C44 . H442 . 109.7 no C44 . N45 . C46 . 121.7(3) yes C44 . N45 . H451 . 118.9 no C46 . N45 . H451 . 119.5 no C2 . C46 . N45 . 115.3(3) yes C2 . C46 . O47 . 121.9(4) yes N45 . C46 . O47 . 122.8(4) yes C102 . C101 . C106 . 120.1(3) yes C102 . C101 . H1011 . 120.3 no C106 . C101 . H1011 . 119.6 no C101 . C102 . C103 . 119.7(3) yes C101 . C102 . C146 . 123.3(3) yes C103 . C102 . C146 . 116.8(3) yes C102 . C103 . C104 . 121.6(3) yes C102 . C103 . H1031 . 117.9 no C104 . C103 . H1031 . 120.5 no C103 . C104 . C105 . 117.3(3) yes C103 . C104 . C107 . 122.7(4) yes C105 . C104 . C107 . 119.8(4) yes C104 . C105 . C106 . 122.1(3) yes C104 . C105 . H1051 . 118.2 no C106 . C105 . H1051 . 119.7 no C101 . C106 . C105 . 119.2(3) yes C101 . C106 . C111 . 123.1(3) yes C105 . C106 . C111 . 117.6(3) yes C104 . C107 . C108 . 107.5(4) yes C104 . C107 . C109 . 112.0(4) yes C108 . C107 . C109 . 111.6(5) yes C104 . C107 . C110 . 109.1(4) yes C108 . C107 . C110 . 109.1(5) yes C109 . C107 . C110 . 107.5(5) yes C107 . C108 . H1083 . 106.8 no C107 . C108 . H1082 . 104.4 no H1083 . C108 . H1082 . 111.1 no C107 . C108 . H1081 . 108.8 no H1083 . C108 . H1081 . 110.8 no H1082 . C108 . H1081 . 114.4 no C107 . C109 . H1093 . 108.3 no C107 . C109 . H1092 . 105.9 no H1093 . C109 . H1092 . 111.3 no C107 . C109 . H1091 . 109.3 no H1093 . C109 . H1091 . 109.7 no H1092 . C109 . H1091 . 112.3 no C107 . C110 . H1103 . 107.8 no C107 . C110 . H1102 . 105.5 no H1103 . C110 . H1102 . 110.7 no C107 . C110 . H1101 . 108.3 no H1103 . C110 . H1101 . 109.5 no H1102 . C110 . H1101 . 114.7 no C106 . C111 . O112 . 121.8(3) yes C106 . C111 . N113 . 116.9(3) yes O112 . C111 . N113 . 121.3(3) yes C111 . N113 . C114 . 122.7(3) yes C111 . N113 . H1131 . 118.8 no C114 . N113 . H1131 . 117.1 no N113 . C114 . C115 . 111.2(3) yes N113 . C114 . H1142 . 109.3 no C115 . C114 . H1142 . 109.4 no N113 . C114 . H1141 . 107.9 no C115 . C114 . H1141 . 109.5 no H1142 . C114 . H1141 . 109.4 no C114 . C115 . O116 . 105.3(3) yes C114 . C115 . H1151 . 111.3 no O116 . C115 . H1151 . 110.6 no C114 . C115 . H1152 . 110.6 no O116 . C115 . H1152 . 108.6 no H1151 . C115 . H1152 . 110.2 no C115 . O116 . C117 . 117.7(3) yes O116 . C117 . C118 . 124.6(3) yes O116 . C117 . C122 . 115.7(3) yes C118 . C117 . C122 . 119.7(3) yes C117 . C118 . C119 . 120.0(3) yes C117 . C118 . H1181 . 120.4 no C119 . C118 . H1181 . 119.6 no C118 . C119 . C120 . 120.0(3) yes C118 . C119 . H1191 . 121.1 no C120 . C119 . H1191 . 118.8 no C119 . C120 . C121 . 119.4(3) yes C119 . C120 . O123 . 124.8(3) yes C121 . C120 . O123 . 115.8(3) yes C120 . C121 . C122 . 120.4(3) yes C120 . C121 . H1211 . 120.9 no C122 . C121 . H1211 . 118.7 no C117 . C122 . C121 . 120.4(3) yes C117 . C122 . H1221 . 119.2 no C121 . C122 . H1221 . 120.4 no C120 . O123 . C124 . 117.3(3) yes O123 . C124 . C125 . 108.2(3) yes O123 . C124 . H1241 . 108.6 no C125 . C124 . H1241 . 110.7 no O123 . C124 . H1242 . 108.2 no C125 . C124 . H1242 . 111.0 no H1241 . C124 . H1242 . 110.0 no C124 . C125 . O126 . 107.9(3) yes C124 . C125 . H1251 . 110.8 no O126 . C125 . H1251 . 109.1 no C124 . C125 . H1252 . 111.1 no O126 . C125 . H1252 . 109.9 no H1251 . C125 . H1252 . 108.1 no C125 . O126 . C127 . 112.9(3) yes O126 . C127 . C128 . 110.1(3) yes O126 . C127 . H1272 . 109.3 no C128 . C127 . H1272 . 109.8 no O126 . C127 . H1271 . 107.7 no C128 . C127 . H1271 . 109.6 no H1272 . C127 . H1271 . 110.3 no C127 . C128 . O129 . 113.7(3) yes C127 . C128 . H1281 . 108.3 no O129 . C128 . H1281 . 107.0 no C127 . C128 . H1282 . 109.1 no O129 . C128 . H1282 . 108.8 no H1281 . C128 . H1282 . 109.9 no C128 . O129 . C130 . 114.4(3) yes O129 . C130 . C131 . 108.2(3) yes O129 . C130 . H1301 . 111.4 no C131 . C130 . H1301 . 109.1 no O129 . C130 . H1302 . 109.0 no C131 . C130 . H1302 . 107.5 no H1301 . C130 . H1302 . 111.6 no C130 . C131 . O132 . 108.2(3) yes C130 . C131 . H1312 . 110.3 no O132 . C131 . H1312 . 108.6 no C130 . C131 . H1311 . 110.4 no O132 . C131 . H1311 . 109.0 no H1312 . C131 . H1311 . 110.2 no C131 . O132 . C133 . 112.0(3) yes O132 . C133 . C134 . 109.9(3) yes O132 . C133 . H1331 . 109.3 no C134 . C133 . H1331 . 109.2 no O132 . C133 . H1332 . 108.0 no C134 . C133 . H1332 . 110.9 no H1331 . C133 . H1332 . 109.5 no C133 . C134 . O135 . 108.9(3) yes C133 . C134 . H1341 . 109.9 no O135 . C134 . H1341 . 108.2 no C133 . C134 . H1342 . 109.8 no O135 . C134 . H1342 . 110.6 no H1341 . C134 . H1342 . 109.3 no C134 . O135 . C136 . 117.1(3) yes O135 . C136 . C137 . 115.7(3) yes O135 . C136 . C141 . 124.7(3) yes C137 . C136 . C141 . 119.6(3) yes C136 . C137 . C138 . 120.1(3) yes C136 . C137 . H1371 . 119.1 no C138 . C137 . H1371 . 120.7 no C137 . C138 . C139 . 120.8(3) yes C137 . C138 . H1381 . 119.6 no C139 . C138 . H1381 . 119.6 no C138 . C139 . C140 . 119.4(3) yes C138 . C139 . O142 . 115.3(3) yes C140 . C139 . O142 . 125.3(3) yes C139 . C140 . C141 . 120.0(3) yes C139 . C140 . H1401 . 119.8 no C141 . C140 . H1401 . 120.2 no C140 . C141 . C136 . 120.1(3) yes C140 . C141 . H1411 . 119.5 no C136 . C141 . H1411 . 120.4 no C139 . O142 . C143 . 117.7(3) yes O142 . C143 . C144 . 107.2(3) yes O142 . C143 . H1431 . 111.5 no C144 . C143 . H1431 . 110.2 no O142 . C143 . H1432 . 108.3 no C144 . C143 . H1432 . 110.2 no H1431 . C143 . H1432 . 109.4 no C143 . C144 . N145 . 109.3(3) yes C143 . C144 . H1442 . 108.8 no N145 . C144 . H1442 . 111.9 no C143 . C144 . H1441 . 108.9 no N145 . C144 . H1441 . 109.8 no H1442 . C144 . H1441 . 108.1 no C144 . N145 . C146 . 121.0(3) yes C144 . N145 . H1451 . 119.5 no C146 . N145 . H1451 . 119.6 no C102 . C146 . N145 . 115.7(3) yes C102 . C146 . O147 . 121.9(4) yes N145 . C146 . O147 . 122.4(4) yes Cl302 . C301 . Cl303 . 114.599(10) yes Cl302 . C301 . H3011 . 108.6 no Cl303 . C301 . H3011 . 107.4 no Cl302 . C301 . H3012 . 108.5 no Cl303 . C301 . H3012 . 108.1 no H3011 . C301 . H3012 . 109.5 no Cl305 . C304 . Cl306 . 114.600(10) yes Cl305 . C304 . H3042 . 111.2 no Cl306 . C304 . H3042 . 108.7 no Cl305 . C304 . H3041 . 104.0 no Cl306 . C304 . H3041 . 108.6 no H3042 . C304 . H3041 . 109.5 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 C101 . H1011 . O23 . 166 0.96 2.54 3.478(6) yes C124 . H1242 . O12 1_655 129 0.97 2.46 3.167(6) yes C143 . H1431 . O12 2_676 153 0.98 2.55 3.444(6) yes C1 . H11 . O123 . 170 0.93 2.56 3.477(6) yes C43 . H431 . O112 2_766 153 0.99 2.47 3.374(6) yes C24 . H242 . O112 1_455 131 0.98 2.45 3.174(6) yes N13 . H131 . O123 . 159 0.88 2.22 3.057(6) yes N113 . H1131 . O23 . 155 0.88 2.24 3.061(6) yes N113 . H1131 . O26 . 126 0.88 2.53 3.126(6) yes C301 . H3011 . O47 . 149 0.95 2.25 3.102(6) yes C301 . H3012 . O147 1_544 163 0.95 2.39 3.313(6) yes C304 . H3042 . C8 1_655 148 0.95 2.59 3.430(6) yes C304 . H3041 . O147 1_544 136 0.95 2.56 3.317(6) yes _chemical_name_common . #===END #============================================================================== data_C6F5I _database_code_depnum_ccdc_archive 'CCDC 815172' #TrackingRef '- crystallographicdata.cif' #============================================================================== _audit_creation_date 11-01-20 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 005CJS10 _chemical_name_systematic . _chemical_melting_point . # start Validation Reply Form _vrf_REFNR01_C6F5I ; PROBLEM: Ratio of reflections to parameters is < 6 for a RESPONSE: The sample diffracted very weakly, and at high angles the reflections were completely absent, even when subjected to synchrotron radiation. This is ascribed to the high level of disorder, which also contributes to the number of parameters. ; _vrf_PLAT026_C6F5I ; 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. This is ascribed to the high level of disorder ; # end Validation Reply Form _cell_length_a 50.61(3) _cell_length_b 9.703(6) _cell_length_c 19.082(11) _cell_angle_alpha 90 _cell_angle_beta 110.460(6) _cell_angle_gamma 90 _cell_volume 8779(9) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z x,-y,z+1/2 -x,y,-z+1/2 x+1/2,-y+1/2,z+1/2 -x+1/2,y+1/2,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 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 0.0311 0.0180 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 0.0492 0.0322 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' I -0.3257 6.8362 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' F 0.0727 0.0534 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' _cell_formula_units_Z 8 # Given Formula = C36 F1 I1 N5 O2 # Dc = 1.03 Fooo = 3856.00 Mu = 60.06 M = 680.33 # Found Formula = C42 H46.00 F5 I1 N2 O9 # Dc = 1.43 FOOO = 3856.00 Mu = 63.86 M = 944.73 _chemical_formula_sum 'C42 H46.00 F5 I1 N2 O9' _chemical_formula_moiety 'C36 H46 N2 O9, C6 F5 I' _chemical_compound_source . _chemical_formula_weight 944.73 _cell_measurement_reflns_used 15684 _cell_measurement_theta_min 2 _cell_measurement_theta_max 63 _cell_measurement_temperature 150 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_min 0.034 _exptl_crystal_size_mid 0.051 _exptl_crystal_size_max 0.368 _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 3856.000 _exptl_absorpt_coefficient_mu 0.290 # Sheldrick geometric approximatio 0.72 0.80 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrystalClear (Rigaku, 1997--2002)' _exptl_absorpt_correction_T_min 0.40 _exptl_absorpt_correction_T_max 0.80 _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--2002)' _computing_cell_refinement 'CrystalClear (Rigaku, 1997--2002)' _computing_data_reduction 'CrystalClear (Rigaku, 1997--2002)' _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 50232 _reflns_number_total 14914 _diffrn_reflns_av_R_equivalents 0.108 # Number of reflections without Friedels Law is 49855 # Number of reflections with Friedels Law is 14914 # Theoretical number of reflections is about 5171 _diffrn_reflns_theta_min 0.832 _diffrn_reflns_theta_max 31.712 _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 29.492 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -76 _diffrn_reflns_limit_h_max 68 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -76 _reflns_limit_h_max 68 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _oxford_diffrn_Wilson_B_factor 4.91 _oxford_diffrn_Wilson_scale 2.16 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.73 _refine_diff_density_max 0.82 # 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>2.0\s(I) _refine_ls_number_reflns 3934 _refine_ls_number_restraints 1387 _refine_ls_number_parameters 832 _oxford_refine_ls_R_factor_ref 0.0917 _refine_ls_wR_factor_ref 0.1028 _refine_ls_goodness_of_fit_ref 1.2305 _refine_ls_shift/su_max 0.0007897 _refine_ls_shift/su_mean 0.0000487 # The values computed from all data _oxford_reflns_number_all 5110 _refine_ls_R_factor_all 0.1126 _refine_ls_wR_factor_all 0.1154 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3934 _refine_ls_R_factor_gt 0.0917 _refine_ls_wR_factor_gt 0.1028 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment 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: 12.5 4.86 9.46 3.25 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement 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 C1 C 0.87389(14) 0.3522(9) 0.6014(4) 0.0579 1.0000 Uani . U . . . . . C2 C 0.86976(14) 0.4764(9) 0.5630(4) 0.0592 1.0000 Uani . U . . . . . C3 C 0.88940(15) 0.5856(10) 0.5894(4) 0.0646 1.0000 Uani . U . . . . . C4 C 0.91366(15) 0.5715(10) 0.6543(4) 0.0673 1.0000 Uani . U . . . . . C5 C 0.91715(14) 0.4450(10) 0.6908(4) 0.0661 1.0000 Uani . U . . . . . C6 C 0.89746(14) 0.3342(9) 0.6673(4) 0.0640 1.0000 Uani . U . . . . . C7 C 0.93565(15) 0.6873(9) 0.6837(4) 0.0857 1.0000 Uani D U . . . . . C8 C 0.9257(2) 0.8253(9) 0.6415(5) 0.0940 0.893(12) Uani D U P 1 1 . . C9 C 0.9417(3) 0.7106(12) 0.7677(4) 0.1084 0.893(12) Uani D U P 1 1 . . C10 C 0.96260(18) 0.6410(12) 0.6705(7) 0.1043 0.893(12) Uani D U P 1 1 . . C11 C 0.90231(17) 0.2066(10) 0.7128(4) 0.0741 1.0000 Uani . U . . . . . O12 O 0.92631(14) 0.1749(8) 0.7542(4) 0.1138 1.0000 Uani . U . . . . . N13 N 0.88004(15) 0.1253(10) 0.7058(4) 0.0943 1.0000 Uani . U . . . . . C14 C 0.8806(2) 0.0066(13) 0.7528(6) 0.0988 1.0000 Uani . U . . . . . C15 C 0.85044(19) -0.0264(11) 0.7503(5) 0.0820 1.0000 Uani . U . . . . . O16 O 0.84051(11) 0.0921(6) 0.7786(2) 0.0715 1.0000 Uani . U . . . . . C17 C 0.8134(2) 0.0963(14) 0.7875(5) 0.0542 0.484(8) Uani D U P . 1 . . C18 C 0.8072(3) 0.2180(13) 0.8177(5) 0.0542 0.484(8) Uani D U P . 1 . . C19 C 0.7815(3) 0.2332(12) 0.8287(5) 0.0538 0.484(8) Uani D U P . 1 . . C20 C 0.7618(2) 0.1259(12) 0.8093(5) 0.0539 0.484(8) Uani D U P . 1 . . C21 C 0.7680(3) 0.0030(11) 0.7793(5) 0.0547 0.484(8) Uani D U P . 1 . . C22 C 0.7937(3) -0.0107(13) 0.7679(5) 0.0549 0.484(8) Uani D U P . 1 . . O23 O 0.7365(2) 0.1481(10) 0.8204(4) 0.0590 0.484(8) Uani D U P . 1 . . C24 C 0.7203(3) 0.0350(16) 0.8330(10) 0.0690 0.484(8) Uani D U P . 1 . . C25 C 0.6926(3) 0.073(3) 0.8399(9) 0.0729 0.484(8) Uani D U P . 1 . . O26 O 0.6731(3) 0.097(2) 0.7651(10) 0.0755 0.484(8) Uani D U P . 1 . . C27 C 0.6443(3) 0.072(3) 0.7586(9) 0.0823 0.484(8) Uani D U P . 1 . . C28 C 0.6254(5) 0.074(2) 0.6783(9) 0.0898 0.484(8) Uani D U P . 1 . . O29 O 0.6228(4) 0.2129(18) 0.6509(8) 0.0824 0.484(8) Uani D U P . 1 . . C30 C 0.6031(4) 0.223(2) 0.5751(9) 0.0840 0.484(8) Uani D U P . 1 . . C31 C 0.6047(3) 0.364(2) 0.5448(12) 0.0816 0.484(8) Uani D U P . 1 . . O32 O 0.6325(3) 0.3859(18) 0.5412(10) 0.0780 0.484(8) Uani D U P . 1 . . C33 C 0.6357(4) 0.5206(19) 0.5130(13) 0.0804 0.484(8) Uani D U P . 1 . . C34 C 0.6650(4) 0.538(2) 0.5126(12) 0.0722 0.484(8) Uani D U P . 1 . . O35 O 0.66674(11) 0.4331(6) 0.4602(3) 0.0737 1.0000 Uani D U . . . . . C36 C 0.69318(16) 0.4434(8) 0.4524(4) 0.0563 1.0000 Uani . U . . . . . C37 C 0.7108(2) 0.5576(8) 0.4728(5) 0.0744 1.0000 Uani . U . . . . . C38 C 0.7363(2) 0.5594(8) 0.4612(5) 0.0777 1.0000 Uani . U . . . . . C39 C 0.74586(16) 0.4478(7) 0.4314(4) 0.0541 1.0000 Uani . U . . . . . C40 C 0.72809(16) 0.3346(9) 0.4108(5) 0.0676 1.0000 Uani . U . . . . . C41 C 0.70240(16) 0.3356(9) 0.4213(5) 0.0714 1.0000 Uani . U . . . . . O42 O 0.77209(10) 0.4597(5) 0.4248(3) 0.0601 1.0000 Uani . U . . . . . C43 C 0.78080(16) 0.3484(9) 0.3872(4) 0.0631 1.0000 Uani . U . . . . . C44 C 0.80931(16) 0.3894(11) 0.3812(4) 0.0723 1.0000 Uani . U . . . . . N45 N 0.83264(12) 0.3882(8) 0.4529(3) 0.0669 1.0000 Uani . U . . . . . C46 C 0.84456(15) 0.5042(11) 0.4933(4) 0.0624 1.0000 Uani . U . . . . . O47 O 0.83544(14) 0.6201(8) 0.4749(3) 0.0879 1.0000 Uani . U . . . . . C101 C 1.0011(2) 0.1768(16) 0.6228(5) 0.0857 0.512(8) Uani D U P . 3 . . C102 C 1.0084(2) 0.0489(13) 0.6049(5) 0.0869 0.512(8) Uani D U P . 3 . . C103 C 1.0297(2) 0.0301(11) 0.5766(5) 0.0879 0.512(8) Uani D U P . 3 . . C104 C 1.0441(2) 0.1442(14) 0.5677(5) 0.0919 0.512(8) Uani D U P . 3 . . C105 C 1.0377(2) 0.2743(12) 0.5850(5) 0.0925 0.512(8) Uani D U P . 3 . . C106 C 1.0161(2) 0.2879(12) 0.6130(5) 0.0905 0.512(8) Uani D U P . 3 . . I107 I 0.96843(7) 0.1857(4) 0.6690(2) 0.0808 0.512(8) Uani D U P . 3 . . F108 F 0.99349(18) -0.0655(12) 0.6129(4) 0.0899 0.512(8) Uani D U P . 3 . . F109 F 1.03682(19) -0.0997(11) 0.5591(4) 0.0914 0.512(8) Uani D U P . 3 . . F110 F 1.06519(18) 0.1201(15) 0.5394(4) 0.0942 0.512(8) Uani D U P . 3 . . F111 F 1.05343(18) 0.3843(12) 0.5759(5) 0.0982 0.512(8) Uani D U P . 3 . . F112 F 1.00894(19) 0.4157(11) 0.6330(4) 0.0952 0.512(8) Uani D U P . 3 . . C117 C 0.8148(2) 0.0726(15) 0.7882(5) 0.0641 0.516(8) Uani D U P . 2 . . C118 C 0.8053(2) 0.1834(13) 0.8201(5) 0.0628 0.516(8) Uani D U P . 2 . . C119 C 0.7796(2) 0.1712(12) 0.8321(5) 0.0636 0.516(8) Uani D U P . 2 . . C120 C 0.7636(2) 0.0500(13) 0.8122(5) 0.0646 0.516(8) Uani D U P . 2 . . C121 C 0.7737(2) -0.0590(13) 0.7814(5) 0.0650 0.516(8) Uani D U P . 2 . . C122 C 0.7992(2) -0.0490(14) 0.7689(5) 0.0645 0.516(8) Uani D U P . 2 . . O123 O 0.7369(2) 0.0181(11) 0.8201(4) 0.0702 0.516(8) Uani D U P . 2 . . C124 C 0.7267(3) 0.1286(17) 0.8538(10) 0.0734 0.516(8) Uani D U P . 2 . . C125 C 0.6987(3) 0.076(3) 0.8515(9) 0.0743 0.516(8) Uani D U P . 2 . . O126 O 0.6778(3) 0.080(2) 0.7773(8) 0.0676 0.516(8) Uani D U P . 2 . . C127 C 0.6508(3) 0.028(2) 0.7736(8) 0.0676 0.516(8) Uani D U P . 2 . . C128 C 0.6321(4) 0.0194(14) 0.6934(8) 0.0710 0.516(8) Uani D U P . 2 . . O129 O 0.6249(3) 0.1554(12) 0.6622(6) 0.0580 0.516(8) Uani D U P . 2 . . C130 C 0.6056(3) 0.1522(16) 0.5859(6) 0.0586 0.516(8) Uani D U P . 2 . . C131 C 0.6043(3) 0.2957(15) 0.5556(10) 0.0572 0.516(8) Uani D U P . 2 . . O132 O 0.6309(2) 0.3345(12) 0.5490(8) 0.0573 0.516(8) Uani D U P . 2 . . C133 C 0.6298(3) 0.4690(15) 0.5166(11) 0.0647 0.516(8) Uani D U P . 2 . . C134 C 0.6580(3) 0.5103(18) 0.5136(10) 0.0634 0.516(8) Uani D U P . 2 . . C201 C 0.9996(3) 0.1985(19) 0.6099(5) 0.1119 0.488(8) Uani D U P . 4 . . C202 C 1.0127(3) 0.0773(16) 0.6047(5) 0.1117 0.488(8) Uani D U P . 4 . . C203 C 1.0360(3) 0.0742(14) 0.5833(5) 0.1120 0.488(8) Uani D U P . 4 . . C204 C 1.0463(2) 0.1964(18) 0.5678(5) 0.1144 0.488(8) Uani D U P . 4 . . C205 C 1.0336(3) 0.3195(15) 0.5719(5) 0.1164 0.488(8) Uani D U P . 4 . . C206 C 1.0103(3) 0.3186(15) 0.5933(6) 0.1148 0.488(8) Uani D U P . 4 . . I207 I 0.96329(8) 0.2252(6) 0.6420(3) 0.1100 0.488(8) Uani D U P . 4 . . F208 F 1.0035(2) -0.0475(16) 0.6204(5) 0.1134 0.488(8) Uani D U P . 4 . . F209 F 1.0481(2) -0.0502(14) 0.5788(5) 0.1132 0.488(8) Uani D U P . 4 . . F210 F 1.0701(2) 0.1988(18) 0.5479(5) 0.1150 0.488(8) Uani D U P . 4 . . F211 F 1.0438(2) 0.4423(15) 0.5561(5) 0.1217 0.488(8) Uani D U P . 4 . . F212 F 1.0000(2) 0.4493(14) 0.5954(5) 0.1191 0.488(8) Uani D U P . 4 . . C49 C 0.9228(12) 0.816(5) 0.707(3) 0.0837 0.107(12) Uani D U P 1 2 . . C50 C 0.9581(11) 0.624(6) 0.754(2) 0.0896 0.107(12) Uani D U P 1 2 . . C48 C 0.9496(13) 0.728(8) 0.627(3) 0.0915 0.107(12) Uani D U P 1 2 . . H11 H 0.8609 0.2793 0.5843 0.0728 1.0000 Uiso R . . . . . . H31 H 0.8860 0.6704 0.5628 0.0798 1.0000 Uiso R . . . . . . H51 H 0.9330 0.4304 0.7325 0.0798 1.0000 Uiso R . . . . . . H81 H 0.9388 0.8987 0.6649 0.1394 0.893(12) Uiso R . P 1 1 . . H82 H 0.9250 0.8092 0.5900 0.1390 0.893(12) Uiso R . P 1 1 . . H83 H 0.9069 0.8463 0.6417 0.1393 0.893(12) Uiso R . P 1 1 . . H93 H 0.9522 0.7965 0.7809 0.1540 0.893(12) Uiso R . P 1 1 . . H92 H 0.9523 0.6343 0.7984 0.1543 0.893(12) Uiso R . P 1 1 . . H91 H 0.9234 0.7220 0.7728 0.1538 0.893(12) Uiso R . P 1 1 . . H101 H 0.9753 0.7181 0.6827 0.1451 0.893(12) Uiso R . P 1 1 . . H102 H 0.9704 0.5647 0.7047 0.1452 0.893(12) Uiso R . P 1 1 . . H103 H 0.9579 0.6134 0.6187 0.1454 0.893(12) Uiso R . P 1 1 . . H141 H 0.8919 0.0354 0.8030 0.1356 1.0000 Uiso R . . . . . . H142 H 0.8892 -0.0708 0.7371 0.1355 1.0000 Uiso R . . . . . . H151 H 0.8504 -0.1067 0.7816 0.0985 1.0000 Uiso R . . . . . . H152 H 0.8379 -0.0447 0.6986 0.0985 1.0000 Uiso R . . . . . . H242 H 0.7316 -0.0103 0.8791 0.0792 0.484(8) Uiso DR . P . 1 . . H241 H 0.7161 -0.0295 0.7915 0.0792 0.484(8) Uiso DR . P . 1 . . H251 H 0.6954 0.1589 0.8669 0.0693 0.484(8) Uiso DR . P . 1 . . H252 H 0.6851 0.0033 0.8634 0.0691 0.484(8) Uiso DR . P . 1 . . H272 H 0.6444 -0.0117 0.7860 0.1035 0.484(8) Uiso DR . P . 1 . . H271 H 0.6389 0.1492 0.7824 0.1030 0.484(8) Uiso DR . P . 1 . . H282 H 0.6331 0.0134 0.6501 0.1053 0.484(8) Uiso DR . P . 1 . . H281 H 0.6068 0.0424 0.6748 0.1049 0.484(8) Uiso DR . P . 1 . . H302 H 0.6061 0.1577 0.5410 0.0922 0.484(8) Uiso DR . P . 1 . . H301 H 0.5845 0.2078 0.5788 0.0920 0.484(8) Uiso DR . P . 1 . . H312 H 0.6027 0.4292 0.5807 0.0950 0.484(8) Uiso DR . P . 1 . . H311 H 0.5897 0.3795 0.4970 0.0950 0.484(8) Uiso DR . P . 1 . . H331 H 0.6334 0.5874 0.5486 0.0992 0.484(8) Uiso DR . P . 1 . . H332 H 0.6207 0.5348 0.4644 0.0991 0.484(8) Uiso DR . P . 1 . . H342 H 0.6798 0.5352 0.5615 0.0851 0.484(8) Uiso DR . P . 1 . . H341 H 0.6656 0.6249 0.4880 0.0852 0.484(8) Uiso DR . P . 1 . . H371 H 0.7048 0.6332 0.4930 0.0876 1.0000 Uiso R . . . . . . H381 H 0.7478 0.6381 0.4745 0.0941 1.0000 Uiso R . . . . . . H401 H 0.7343 0.2568 0.3906 0.0829 1.0000 Uiso R . . . . . . H411 H 0.6908 0.2593 0.4066 0.0888 1.0000 Uiso R . . . . . . H431 H 0.7834 0.2644 0.4164 0.0749 1.0000 Uiso R . . . . . . H432 H 0.7665 0.3343 0.3381 0.0740 1.0000 Uiso R . . . . . . H442 H 0.8135 0.3309 0.3456 0.0885 1.0000 Uiso R . . . . . . H441 H 0.8068 0.4864 0.3655 0.0883 1.0000 Uiso R . . . . . . H1241 H 0.7400 0.1465 0.9040 0.0851 0.516(8) Uiso DR . P . 2 . . H1242 H 0.7242 0.2103 0.8233 0.0852 0.516(8) Uiso DR . P . 2 . . H1251 H 0.7011 -0.0153 0.8735 0.0939 0.516(8) Uiso DR . P . 2 . . H1252 H 0.6921 0.1408 0.8805 0.0942 0.516(8) Uiso DR . P . 2 . . H1271 H 0.6533 -0.0653 0.7941 0.0851 0.516(8) Uiso DR . P . 2 . . H1272 H 0.6414 0.0877 0.7986 0.0853 0.516(8) Uiso DR . P . 2 . . H1281 H 0.6443 -0.0149 0.6673 0.0893 0.516(8) Uiso DR . P . 2 . . H1282 H 0.6157 -0.0415 0.6825 0.0894 0.516(8) Uiso DR . P . 2 . . H1302 H 0.6139 0.0885 0.5604 0.0672 0.516(8) Uiso DR . P . 2 . . H1301 H 0.5867 0.1199 0.5811 0.0670 0.516(8) Uiso DR . P . 2 . . H1312 H 0.5997 0.3586 0.5885 0.0653 0.516(8) Uiso DR . P . 2 . . H1311 H 0.5895 0.3002 0.5063 0.0650 0.516(8) Uiso DR . P . 2 . . H1332 H 0.6222 0.5336 0.5432 0.0813 0.516(8) Uiso DR . P . 2 . . H1331 H 0.6176 0.4665 0.4642 0.0811 0.516(8) Uiso DR . P . 2 . . H1342 H 0.6715 0.4842 0.5621 0.0829 0.516(8) Uiso DR . P . 2 . . H1341 H 0.6590 0.6085 0.5057 0.0833 0.516(8) Uiso DR . P . 2 . . H1181 H 0.8157 0.2672 0.8328 0.0635 0.516(8) Uiso DR . P . 2 . . H1191 H 0.7728 0.2442 0.8543 0.0689 0.516(8) Uiso DR . P . 2 . . H191 H 0.7774 0.3159 0.8495 0.0505 0.484(8) Uiso DR . P . 1 . . H181 H 0.8206 0.2908 0.8304 0.0600 0.484(8) Uiso DR . P . 1 . . H1211 H 0.7633 -0.1425 0.7685 0.0651 0.516(8) Uiso DR . P . 2 . . H1221 H 0.8062 -0.1231 0.7480 0.0697 0.516(8) Uiso DR . P . 2 . . H211 H 0.7548 -0.0707 0.7670 0.0485 0.484(8) Uiso DR . P . 1 . . H221 H 0.7977 -0.0932 0.7466 0.0620 0.484(8) Uiso DR . P . 1 . . H451 H 0.8395 0.3102 0.4702 0.0722 1.0000 Uiso R . . . . . . H131 H 0.8646 0.1440 0.6708 0.1154 1.0000 Uiso R . . . . . . H502 H 0.9668 0.5483 0.7387 0.0956 0.107(12) Uiso R . P 1 2 . . H503 H 0.9718 0.6934 0.7751 0.0956 0.107(12) Uiso R . P 1 2 . . H501 H 0.9502 0.5943 0.7895 0.0956 0.107(12) Uiso R . P 1 2 . . H493 H 0.9157 0.7869 0.7444 0.0831 0.107(12) Uiso R . P 1 2 . . H491 H 0.9363 0.8868 0.7262 0.0831 0.107(12) Uiso R . P 1 2 . . H492 H 0.9077 0.8495 0.6649 0.0831 0.107(12) Uiso R . P 1 2 . . H481 H 0.9349 0.7646 0.5849 0.1215 0.107(12) Uiso R . P 1 2 . . H482 H 0.9639 0.7959 0.6461 0.1215 0.107(12) Uiso R . P 1 2 . . H483 H 0.9574 0.6492 0.6120 0.1215 0.107(12) Uiso R . P 1 2 . . 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 0.036(3) 0.099(4) 0.038(3) -0.018(2) 0.0123(18) -0.002(3) C2 0.043(3) 0.105(4) 0.033(3) -0.015(2) 0.0180(17) -0.012(2) C3 0.042(3) 0.106(4) 0.047(3) -0.018(3) 0.0167(19) -0.011(3) C4 0.038(3) 0.105(3) 0.056(4) -0.032(3) 0.0136(19) 0.002(3) C5 0.033(3) 0.104(4) 0.053(4) -0.033(3) 0.005(3) 0.011(3) C6 0.036(3) 0.102(4) 0.048(3) -0.022(2) 0.0077(19) 0.009(2) C7 0.051(3) 0.114(4) 0.076(4) -0.033(4) 0.002(3) -0.007(3) C8 0.068(6) 0.110(4) 0.089(6) -0.030(5) 0.008(5) -0.013(4) C9 0.112(9) 0.108(9) 0.076(4) -0.043(4) -0.003(5) -0.003(7) C10 0.049(4) 0.113(8) 0.144(10) -0.036(8) 0.025(6) -0.022(4) C11 0.053(2) 0.111(4) 0.048(4) -0.016(3) 0.004(3) 0.013(3) O12 0.064(3) 0.119(5) 0.113(5) 0.004(4) -0.025(3) 0.002(3) N13 0.052(3) 0.147(6) 0.072(4) 0.035(4) 0.007(3) 0.014(3) C14 0.074(4) 0.128(6) 0.089(6) 0.034(5) 0.023(4) 0.035(3) C15 0.083(4) 0.102(5) 0.061(5) 0.016(4) 0.025(4) 0.020(4) O16 0.064(2) 0.095(4) 0.052(3) 0.001(3) 0.014(2) -0.004(2) C17 0.067(4) 0.049(4) 0.037(5) 0.007(3) 0.006(4) -0.003(3) C18 0.067(3) 0.048(3) 0.038(4) 0.006(3) 0.008(3) -0.006(2) C19 0.068(3) 0.047(3) 0.038(4) 0.005(3) 0.008(3) -0.007(2) C20 0.068(3) 0.047(3) 0.039(4) 0.005(3) 0.009(3) -0.007(2) C21 0.067(4) 0.046(4) 0.040(4) 0.004(3) 0.005(4) -0.006(3) C22 0.067(4) 0.048(4) 0.038(5) 0.005(3) 0.005(4) -0.003(3) O23 0.072(3) 0.054(4) 0.047(4) 0.004(3) 0.016(3) -0.009(3) C24 0.076(4) 0.068(4) 0.060(4) 0.003(3) 0.020(3) -0.018(3) C25 0.077(4) 0.080(4) 0.060(4) -0.002(3) 0.021(3) -0.019(4) O26 0.074(3) 0.096(4) 0.058(4) -0.001(4) 0.024(3) -0.017(4) C27 0.073(4) 0.112(4) 0.062(4) -0.005(3) 0.024(4) -0.017(4) C28 0.080(3) 0.117(5) 0.065(4) -0.006(3) 0.017(3) -0.012(4) O29 0.071(4) 0.117(5) 0.059(4) -0.009(3) 0.022(3) -0.015(5) C30 0.072(4) 0.116(5) 0.061(4) -0.006(3) 0.021(3) -0.015(5) C31 0.066(4) 0.117(5) 0.069(4) -0.003(3) 0.032(3) -0.009(5) O32 0.066(4) 0.110(5) 0.068(4) -0.006(4) 0.035(3) -0.001(5) C33 0.066(5) 0.110(5) 0.077(4) -0.005(4) 0.039(3) -0.002(4) C34 0.067(5) 0.095(5) 0.069(4) -0.012(3) 0.042(3) 0.004(5) O35 0.063(2) 0.106(4) 0.049(3) -0.017(2) 0.015(2) 0.009(2) C36 0.066(3) 0.069(3) 0.031(3) -0.008(3) 0.013(3) 0.003(2) C37 0.104(4) 0.043(4) 0.087(5) -0.002(3) 0.047(4) 0.003(3) C38 0.105(4) 0.039(3) 0.101(6) -0.005(4) 0.051(5) -0.014(3) C39 0.063(3) 0.042(3) 0.053(4) 0.005(3) 0.015(3) -0.007(2) C40 0.051(3) 0.068(4) 0.079(5) -0.036(4) 0.017(3) -0.016(3) C41 0.053(3) 0.084(4) 0.073(5) -0.048(4) 0.017(3) -0.020(3) O42 0.060(2) 0.059(3) 0.053(3) -0.001(2) 0.011(2) -0.017(2) C43 0.050(3) 0.093(5) 0.037(4) -0.013(3) 0.004(2) -0.015(3) C44 0.059(3) 0.114(6) 0.037(3) -0.009(3) 0.009(2) -0.024(3) N45 0.050(3) 0.108(4) 0.039(3) -0.007(3) 0.0111(19) -0.024(3) C46 0.047(3) 0.103(3) 0.037(3) -0.005(2) 0.0146(18) -0.021(3) O47 0.083(4) 0.102(3) 0.056(3) 0.010(3) -0.003(3) -0.028(3) C101 0.0486(18) 0.128(3) 0.085(2) -0.005(2) 0.0289(15) 0.0123(18) C102 0.051(2) 0.128(3) 0.086(3) -0.003(3) 0.030(2) 0.014(2) C103 0.052(3) 0.130(3) 0.087(3) -0.002(3) 0.031(2) 0.016(2) C104 0.055(3) 0.135(3) 0.091(3) 0.001(3) 0.032(2) 0.013(2) C105 0.055(3) 0.132(3) 0.095(3) 0.002(3) 0.032(2) 0.011(2) C106 0.053(2) 0.130(3) 0.092(3) -0.001(3) 0.029(2) 0.011(2) I107 0.0462(11) 0.1200(16) 0.0789(16) -0.0106(11) 0.0250(10) 0.0102(9) F108 0.055(3) 0.129(3) 0.090(4) -0.002(3) 0.031(3) 0.012(3) F109 0.054(3) 0.132(4) 0.088(4) -0.003(3) 0.025(3) 0.021(3) F110 0.059(3) 0.138(4) 0.093(4) 0.001(3) 0.036(3) 0.012(3) F111 0.057(3) 0.136(4) 0.104(4) 0.008(3) 0.031(3) 0.009(3) F112 0.057(3) 0.129(3) 0.097(4) -0.004(3) 0.025(3) 0.012(3) C117 0.056(4) 0.084(4) 0.042(5) 0.002(4) 0.004(3) -0.001(3) C118 0.055(4) 0.081(4) 0.042(5) 0.002(4) 0.004(3) -0.004(3) C119 0.056(3) 0.082(4) 0.043(4) 0.002(4) 0.006(3) -0.003(3) C120 0.057(3) 0.084(4) 0.046(4) 0.001(3) 0.009(3) -0.004(3) C121 0.056(4) 0.083(4) 0.046(4) 0.000(4) 0.005(3) -0.003(3) C122 0.056(4) 0.084(4) 0.043(5) -0.003(4) 0.004(3) 0.000(3) O123 0.060(3) 0.088(4) 0.058(4) 0.001(3) 0.014(3) -0.005(3) C124 0.063(3) 0.092(4) 0.065(4) 0.002(3) 0.022(3) -0.004(3) C125 0.066(3) 0.097(4) 0.060(4) 0.007(3) 0.022(3) -0.007(4) O126 0.060(4) 0.096(4) 0.055(4) 0.014(3) 0.030(3) -0.010(4) C127 0.059(4) 0.094(4) 0.057(4) 0.015(3) 0.029(3) -0.008(3) C128 0.064(4) 0.087(4) 0.061(4) 0.013(3) 0.021(3) -0.002(3) O129 0.049(4) 0.078(4) 0.050(3) 0.000(3) 0.022(3) -0.004(4) C130 0.051(3) 0.073(4) 0.052(3) -0.001(3) 0.018(3) -0.004(3) C131 0.048(3) 0.071(4) 0.054(3) -0.002(3) 0.019(3) -0.005(4) O132 0.048(3) 0.072(4) 0.054(4) -0.007(3) 0.021(3) -0.006(3) C133 0.059(4) 0.073(4) 0.064(3) -0.005(3) 0.024(3) -0.013(4) C134 0.062(4) 0.075(4) 0.060(4) -0.014(4) 0.030(3) -0.013(4) C201 0.054(2) 0.168(4) 0.115(3) -0.038(3) 0.032(2) -0.002(2) C202 0.053(3) 0.169(4) 0.117(4) -0.032(3) 0.033(2) 0.000(2) C203 0.054(3) 0.170(4) 0.116(4) -0.029(3) 0.034(3) 0.001(3) C204 0.058(3) 0.173(5) 0.116(4) -0.026(3) 0.034(3) 0.000(3) C205 0.059(3) 0.172(4) 0.120(4) -0.024(3) 0.032(3) 0.001(3) C206 0.058(3) 0.169(4) 0.118(4) -0.030(3) 0.031(2) 0.001(2) I207 0.0534(14) 0.163(3) 0.115(3) -0.051(2) 0.0308(16) -0.0082(15) F208 0.052(3) 0.170(4) 0.121(4) -0.031(4) 0.033(3) -0.001(3) F209 0.053(4) 0.172(5) 0.117(4) -0.028(4) 0.032(3) 0.003(3) F210 0.061(3) 0.173(5) 0.115(4) -0.024(4) 0.037(3) -0.001(3) F211 0.064(4) 0.174(5) 0.126(4) -0.017(4) 0.031(3) 0.001(3) F212 0.064(3) 0.170(4) 0.119(4) -0.029(4) 0.026(3) 0.004(3) C49 0.05(3) 0.105(17) 0.07(3) -0.03(2) -0.01(2) -0.006(12) C50 0.06(2) 0.10(3) 0.08(2) -0.044(19) -0.008(14) -0.003(17) C48 0.04(3) 0.13(3) 0.09(2) -0.04(2) 0.002(17) -0.03(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.824(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 C1 . C2 . 1.389(12) yes C1 . C6 . 1.409(10) yes C1 . H11 . 0.943 no C2 . C3 . 1.419(11) yes C2 . C46 . 1.511(11) yes C3 . C4 . 1.414(11) yes C3 . H31 . 0.950 no C4 . C5 . 1.391(12) yes C4 . C7 . 1.542(12) yes C5 . C6 . 1.427(12) yes C5 . H51 . 0.922 no C6 . C11 . 1.482(13) yes C7 . C8 . 1.553(8) yes C7 . C9 . 1.539(7) yes C7 . C10 . 1.538(7) yes C7 . C49 . 1.541(9) yes C7 . C50 . 1.545(9) yes C7 . C48 . 1.539(9) yes C8 . H81 . 0.970 no C8 . H82 . 0.985 no C8 . H83 . 0.973 no C9 . H93 . 0.974 no C9 . H92 . 0.981 no C9 . H91 . 0.969 no C10 . H101 . 0.961 no C10 . H102 . 0.974 no C10 . H103 . 0.970 no C11 . O12 . 1.235(10) yes C11 . N13 . 1.344(12) yes O12 . I207 . 3.335(11) yes N13 . C14 . 1.454(13) yes N13 . H131 . 0.850 no C14 . C15 . 1.545(14) yes C14 . H141 . 0.968 no C14 . H142 . 0.966 no C15 . O16 . 1.434(11) yes C15 . H151 . 0.982 no C15 . H152 . 0.984 no O16 . C117 . 1.387(13) yes C17 . C18 . 1.396(8) yes C17 . C22 . 1.398(8) yes C18 . C19 . 1.397(8) yes C18 . H181 . 0.950 no C19 . C20 . 1.399(8) yes C19 . H191 . 0.950 no C20 . C21 . 1.403(8) yes C20 . O23 . 1.388(16) yes C21 . C22 . 1.400(8) yes C21 . H211 . 0.950 no C22 . H221 . 0.950 no O23 . C24 . 1.439(8) yes C24 . C25 . 1.502(9) yes C24 . H242 . 0.972 no C24 . H241 . 0.972 no C25 . O26 . 1.442(9) yes C25 . H251 . 0.961 no C25 . H252 . 0.960 no O26 . C27 . 1.441(9) yes C27 . C28 . 1.497(9) yes C27 . H272 . 0.965 no C27 . H271 . 0.964 no C28 . O29 . 1.438(9) yes C28 . H282 . 0.968 no C28 . H281 . 0.968 no O29 . C30 . 1.445(9) yes C30 . C31 . 1.497(9) yes C30 . H302 . 0.961 no C30 . H301 . 0.977 no C31 . O32 . 1.446(9) yes C31 . H312 . 0.962 no C31 . H311 . 0.974 no O32 . C33 . 1.443(9) yes C33 . C34 . 1.498(9) yes C33 . H331 . 0.973 no C33 . H332 . 0.979 no C34 . O35 . 1.449(9) yes C34 . H342 . 0.971 no C34 . H341 . 0.973 no O35 . C36 . 1.401(9) yes O35 . C134 . 1.454(8) yes C36 . C37 . 1.390(12) yes C36 . C41 . 1.363(11) yes C37 . C38 . 1.385(13) yes C37 . H371 . 0.926 no C38 . C39 . 1.387(11) yes C38 . H381 . 0.938 no C39 . C40 . 1.386(10) yes C39 . O42 . 1.381(9) yes C40 . C41 . 1.383(12) yes C40 . H401 . 0.951 no C41 . H411 . 0.925 no O42 . C43 . 1.448(9) yes C43 . C44 . 1.539(11) yes C43 . H431 . 0.970 no C43 . H432 . 0.973 no C44 . N45 . 1.462(9) yes C44 . H442 . 0.964 no C44 . H441 . 0.982 no N45 . C46 . 1.378(11) yes N45 . H451 . 0.850 no C46 . O47 . 1.219(11) yes C101 . C102 . 1.373(8) yes C101 . C106 . 1.369(8) yes C101 . I107 . 2.130(12) yes C102 . C103 . 1.374(8) yes C102 . F108 . 1.382(8) yes C103 . C104 . 1.369(8) yes C103 . F109 . 1.382(8) yes C104 . C105 . 1.372(8) yes C104 . F110 . 1.374(8) yes C105 . C106 . 1.381(8) yes C105 . F111 . 1.377(8) yes C106 . F112 . 1.383(8) yes C117 . C118 . 1.401(8) yes C117 . C122 . 1.398(8) yes C118 . C119 . 1.404(8) yes C118 . H1181 . 0.950 no C119 . C120 . 1.404(8) yes C119 . H1191 . 0.950 no C120 . C121 . 1.392(8) yes C120 . O123 . 1.441(16) yes C121 . C122 . 1.394(8) yes C121 . H1211 . 0.950 no C122 . H1221 . 0.950 no O123 . C124 . 1.436(9) yes C124 . C125 . 1.496(9) yes C124 . H1241 . 0.974 no C124 . H1242 . 0.964 no C125 . O126 . 1.441(8) yes C125 . H1251 . 0.969 no C125 . H1252 . 0.968 no O126 . C127 . 1.437(8) yes C127 . C128 . 1.495(9) yes C127 . H1271 . 0.978 no C127 . H1272 . 0.972 no C128 . O129 . 1.441(9) yes C128 . H1281 . 0.976 no C128 . H1282 . 0.981 no O129 . C130 . 1.442(8) yes C130 . C131 . 1.500(9) yes C130 . H1302 . 0.967 no C130 . H1301 . 0.980 no C131 . O132 . 1.449(8) yes C131 . H1312 . 0.960 no C131 . H1311 . 0.978 no O132 . C133 . 1.436(9) yes C133 . C134 . 1.502(9) yes C133 . H1332 . 0.965 no C133 . H1331 . 0.976 no C134 . H1342 . 0.974 no C134 . H1341 . 0.969 no C201 . C202 . 1.370(8) yes C201 . C206 . 1.369(8) yes C201 . I207 . 2.146(14) yes C202 . C203 . 1.375(8) yes C202 . F208 . 1.369(9) yes C203 . C204 . 1.371(8) yes C203 . F209 . 1.372(8) yes C204 . C205 . 1.372(8) yes C204 . F210 . 1.383(8) yes C205 . C206 . 1.375(9) yes C205 . F211 . 1.374(9) yes C206 . F212 . 1.379(8) yes C49 . H493 . 0.950 no C49 . H491 . 0.950 no C49 . H492 . 0.950 no C50 . H502 . 0.950 no C50 . H503 . 0.950 no C50 . H501 . 0.950 no C48 . H481 . 0.950 no C48 . H482 . 0.950 no C48 . H483 . 0.950 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 C2 . C1 . C6 . 120.2(7) yes C2 . C1 . H11 . 120.7 no C6 . C1 . H11 . 119.1 no C1 . C2 . C3 . 120.2(7) yes C1 . C2 . C46 . 123.0(7) yes C3 . C2 . C46 . 116.7(8) yes C2 . C3 . C4 . 121.7(9) yes C2 . C3 . H31 . 119.0 no C4 . C3 . H31 . 119.3 no C3 . C4 . C5 . 116.3(8) yes C3 . C4 . C7 . 122.9(9) yes C5 . C4 . C7 . 120.7(7) yes C4 . C5 . C6 . 123.7(7) yes C4 . C5 . H51 . 119.1 no C6 . C5 . H51 . 117.2 no C5 . C6 . C1 . 117.9(8) yes C5 . C6 . C11 . 119.4(7) yes C1 . C6 . C11 . 122.7(8) yes C4 . C7 . C8 . 112.1(7) yes C4 . C7 . C9 . 109.9(7) yes C8 . C7 . C9 . 108.9(6) yes C4 . C7 . C10 . 107.2(7) yes C8 . C7 . C10 . 108.3(6) yes C9 . C7 . C10 . 110.4(6) yes C4 . C7 . C49 . 112(3) yes C4 . C7 . C50 . 104(3) yes C49 . C7 . C50 . 109.3(9) yes C4 . C7 . C48 . 112(3) yes C49 . C7 . C48 . 109.7(9) yes C50 . C7 . C48 . 109.3(9) yes C7 . C8 . H81 . 110.4 no C7 . C8 . H82 . 105.8 no H81 . C8 . H82 . 110.6 no C7 . C8 . H83 . 108.6 no H81 . C8 . H83 . 110.9 no H82 . C8 . H83 . 110.3 no C7 . C9 . H93 . 106.7 no C7 . C9 . H92 . 112.2 no H93 . C9 . H92 . 110.8 no C7 . C9 . H91 . 105.8 no H93 . C9 . H91 . 109.2 no H92 . C9 . H91 . 111.9 no C7 . C10 . H101 . 106.9 no C7 . C10 . H102 . 106.7 no H101 . C10 . H102 . 110.5 no C7 . C10 . H103 . 109.3 no H101 . C10 . H103 . 111.4 no H102 . C10 . H103 . 111.7 no C6 . C11 . O12 . 120.5(9) yes C6 . C11 . N13 . 118.1(7) yes O12 . C11 . N13 . 121.3(9) yes C11 . O12 . I207 . 101.5(6) yes C11 . N13 . C14 . 124.6(8) yes C11 . N13 . H131 . 117.3 no C14 . N13 . H131 . 118.0 no N13 . C14 . C15 . 109.7(7) yes N13 . C14 . H141 . 105.0 no C15 . C14 . H141 . 109.1 no N13 . C14 . H142 . 109.8 no C15 . C14 . H142 . 112.0 no H141 . C14 . H142 . 111.0 no C14 . C15 . O16 . 107.1(8) yes C14 . C15 . H151 . 110.9 no O16 . C15 . H151 . 109.3 no C14 . C15 . H152 . 110.6 no O16 . C15 . H152 . 109.5 no H151 . C15 . H152 . 109.4 no C15 . O16 . C117 . 114.1(8) yes O16 . C17 . C18 . 115.6(11) yes O16 . C17 . C22 . 124.6(11) yes C18 . C17 . C22 . 119.8(11) yes C17 . C18 . C19 . 120.4(11) yes C17 . C18 . H181 . 119.5 no C19 . C18 . H181 . 120.1 no C18 . C19 . C20 . 119.8(11) yes C18 . C19 . H191 . 120.2 no C20 . C19 . H191 . 120.0 no C19 . C20 . C21 . 120.2(11) yes C19 . C20 . O23 . 117.0(10) yes C21 . C20 . O23 . 122.8(11) yes C20 . C21 . C22 . 119.6(11) yes C20 . C21 . H211 . 120.3 no C22 . C21 . H211 . 120.1 no C21 . C22 . C17 . 120.2(11) yes C21 . C22 . H221 . 119.6 no C17 . C22 . H221 . 120.1 no C20 . O23 . C24 . 121.1(12) yes O23 . C24 . C25 . 115.4(17) yes O23 . C24 . H242 . 107.8 no C25 . C24 . H242 . 107.8 no O23 . C24 . H241 . 109.3 no C25 . C24 . H241 . 106.5 no H242 . C24 . H241 . 109.9 no C24 . C25 . O26 . 106.7(15) yes C24 . C25 . H251 . 107.1 no O26 . C25 . H251 . 108.2 no C24 . C25 . H252 . 113.4 no O26 . C25 . H252 . 109.5 no H251 . C25 . H252 . 111.6 no C25 . O26 . C27 . 112.1(14) yes O26 . C27 . C28 . 110.7(15) yes O26 . C27 . H272 . 106.5 no C28 . C27 . H272 . 116.3 no O26 . C27 . H271 . 105.8 no C28 . C27 . H271 . 106.7 no H272 . C27 . H271 . 110.3 no C27 . C28 . O29 . 109.1(15) yes C27 . C28 . H282 . 108.8 no O29 . C28 . H282 . 111.6 no C27 . C28 . H281 . 109.2 no O29 . C28 . H281 . 107.9 no H282 . C28 . H281 . 110.2 no C28 . O29 . C30 . 111.9(13) yes O29 . C30 . C31 . 109.7(15) yes O29 . C30 . H302 . 114.3 no C31 . C30 . H302 . 107.5 no O29 . C30 . H301 . 105.1 no C31 . C30 . H301 . 110.7 no H302 . C30 . H301 . 109.5 no C30 . C31 . O32 . 109.8(15) yes C30 . C31 . H312 . 106.9 no O32 . C31 . H312 . 106.5 no C30 . C31 . H311 . 111.7 no O32 . C31 . H311 . 112.8 no H312 . C31 . H311 . 108.9 no C31 . O32 . C33 . 112.7(12) yes O32 . C33 . C34 . 110.0(14) yes O32 . C33 . H331 . 106.8 no C34 . C33 . H331 . 106.6 no O32 . C33 . H332 . 109.4 no C34 . C33 . H332 . 114.7 no H331 . C33 . H332 . 109.1 no C33 . C34 . O35 . 103.0(12) yes C33 . C34 . H342 . 115.2 no O35 . C34 . H342 . 115.7 no C33 . C34 . H341 . 107.4 no O35 . C34 . H341 . 104.8 no H342 . C34 . H341 . 109.9 no C36 . O35 . C134 . 125.1(7) yes O35 . C36 . C37 . 124.7(7) yes O35 . C36 . C41 . 118.5(7) yes C37 . C36 . C41 . 116.8(7) yes C36 . C37 . C38 . 120.5(8) yes C36 . C37 . H371 . 118.6 no C38 . C37 . H371 . 120.9 no C37 . C38 . C39 . 122.3(8) yes C37 . C38 . H381 . 119.3 no C39 . C38 . H381 . 118.4 no C38 . C39 . C40 . 116.8(7) yes C38 . C39 . O42 . 117.1(7) yes C40 . C39 . O42 . 126.1(7) yes C39 . C40 . C41 . 120.2(7) yes C39 . C40 . H401 . 117.9 no C41 . C40 . H401 . 121.9 no C40 . C41 . C36 . 123.4(7) yes C40 . C41 . H411 . 118.7 no C36 . C41 . H411 . 117.9 no C39 . O42 . C43 . 116.8(5) yes O42 . C43 . C44 . 107.5(6) yes O42 . C43 . H431 . 110.3 no C44 . C43 . H431 . 108.6 no O42 . C43 . H432 . 109.3 no C44 . C43 . H432 . 111.3 no H431 . C43 . H432 . 109.9 no C43 . C44 . N45 . 113.6(6) yes C43 . C44 . H442 . 110.0 no N45 . C44 . H442 . 110.6 no C43 . C44 . H441 . 104.3 no N45 . C44 . H441 . 105.6 no H442 . C44 . H441 . 112.6 no C44 . N45 . C46 . 124.7(8) yes C44 . N45 . H451 . 117.2 no C46 . N45 . H451 . 118.1 no C2 . C46 . N45 . 114.6(8) yes C2 . C46 . O47 . 122.4(8) yes N45 . C46 . O47 . 123.0(7) yes C102 . C101 . C106 . 117.8(10) yes C102 . C101 . I107 . 117.2(10) yes C106 . C101 . I107 . 125.0(10) yes C101 . C102 . C103 . 122.4(10) yes C101 . C102 . F108 . 119.5(11) yes C103 . C102 . F108 . 118.1(11) yes C102 . C103 . C104 . 117.8(9) yes C102 . C103 . F109 . 121.5(12) yes C104 . C103 . F109 . 120.8(11) yes C103 . C104 . C105 . 122.2(9) yes C103 . C104 . F110 . 115.6(12) yes C105 . C104 . F110 . 122.1(12) yes C104 . C105 . C106 . 117.8(9) yes C104 . C105 . F111 . 119.2(11) yes C106 . C105 . F111 . 123.0(12) yes C105 . C106 . C101 . 122.0(10) yes C105 . C106 . F112 . 120.8(12) yes C101 . C106 . F112 . 117.2(12) yes C101 . I107 . O12 . 172.1(3) yes O16 . C117 . C118 . 115.6(12) yes O16 . C117 . C122 . 123.5(11) yes C118 . C117 . C122 . 120.9(11) yes C117 . C118 . C119 . 119.0(11) yes C117 . C118 . H1181 . 121.7 no C119 . C118 . H1181 . 119.3 no C118 . C119 . C120 . 120.6(11) yes C118 . C119 . H1191 . 120.7 no C120 . C119 . H1191 . 118.7 no C119 . C120 . C121 . 119.1(11) yes C119 . C120 . O123 . 128.8(11) yes C121 . C120 . O123 . 112.1(10) yes C120 . C121 . C122 . 121.2(11) yes C120 . C121 . H1211 . 120.4 no C122 . C121 . H1211 . 118.4 no C117 . C122 . C121 . 119.2(11) yes C117 . C122 . H1221 . 119.2 no C121 . C122 . H1221 . 121.6 no C120 . O123 . C124 . 112.4(11) yes O123 . C124 . C125 . 102.6(15) yes O123 . C124 . H1241 . 109.9 no C125 . C124 . H1241 . 114.2 no O123 . C124 . H1242 . 109.7 no C125 . C124 . H1242 . 109.8 no H1241 . C124 . H1242 . 110.3 no C124 . C125 . O126 . 112.3(14) yes C124 . C125 . H1251 . 108.8 no O126 . C125 . H1251 . 112.9 no C124 . C125 . H1252 . 105.8 no O126 . C125 . H1252 . 105.4 no H1251 . C125 . H1252 . 111.4 no C125 . O126 . C127 . 113.3(11) yes O126 . C127 . C128 . 108.7(12) yes O126 . C127 . H1271 . 108.5 no C128 . C127 . H1271 . 107.7 no O126 . C127 . H1272 . 112.9 no C128 . C127 . H1272 . 107.1 no H1271 . C127 . H1272 . 111.8 no C127 . C128 . O129 . 110.4(11) yes C127 . C128 . H1281 . 104.7 no O129 . C128 . H1281 . 102.5 no C127 . C128 . H1282 . 115.8 no O129 . C128 . H1282 . 113.0 no H1281 . C128 . H1282 . 109.1 no C128 . O129 . C130 . 112.4(10) yes O129 . C130 . C131 . 107.0(11) yes O129 . C130 . H1302 . 105.3 no C131 . C130 . H1302 . 111.7 no O129 . C130 . H1301 . 113.2 no C131 . C130 . H1301 . 110.5 no H1302 . C130 . H1301 . 109.1 no C130 . C131 . O132 . 110.9(10) yes C130 . C131 . H1312 . 109.1 no O132 . C131 . H1312 . 109.7 no C130 . C131 . H1311 . 109.2 no O132 . C131 . H1311 . 109.1 no H1312 . C131 . H1311 . 108.9 no C131 . O132 . C133 . 112.0(10) yes O132 . C133 . C134 . 111.3(12) yes O132 . C133 . H1332 . 109.2 no C134 . C133 . H1332 . 113.7 no O132 . C133 . H1331 . 109.5 no C134 . C133 . H1331 . 103.7 no H1332 . C133 . H1331 . 109.3 no C133 . C134 . O35 . 114.6(11) yes C133 . C134 . H1342 . 105.0 no O35 . C134 . H1342 . 104.1 no C133 . C134 . H1341 . 112.0 no O35 . C134 . H1341 . 110.4 no H1342 . C134 . H1341 . 110.2 no C202 . C201 . C206 . 118.2(12) yes C202 . C201 . I207 . 127.5(12) yes C206 . C201 . I207 . 114.3(12) yes C201 . C202 . C203 . 121.8(12) yes C201 . C202 . F208 . 122.2(14) yes C203 . C202 . F208 . 116.0(14) yes C202 . C203 . C204 . 118.6(11) yes C202 . C203 . F209 . 119.2(14) yes C204 . C203 . F209 . 122.3(14) yes C203 . C204 . C205 . 121.1(11) yes C203 . C204 . F210 . 120.7(15) yes C205 . C204 . F210 . 118.2(15) yes C204 . C205 . C206 . 118.7(11) yes C204 . C205 . F211 . 121.4(15) yes C206 . C205 . F211 . 119.9(15) yes C205 . C206 . C201 . 121.7(12) yes C205 . C206 . F212 . 112.1(14) yes C201 . C206 . F212 . 126.2(15) yes C201 . I207 . O12 . 153.4(5) yes C7 . C49 . H493 . 106.7 no C7 . C49 . H491 . 112.3 no H493 . C49 . H491 . 109.5 no C7 . C49 . H492 . 109.4 no H493 . C49 . H492 . 109.5 no H491 . C49 . H492 . 109.5 no C7 . C50 . H502 . 108.9 no C7 . C50 . H503 . 107.4 no H502 . C50 . H503 . 109.5 no C7 . C50 . H501 . 112.0 no H502 . C50 . H501 . 109.5 no H503 . C50 . H501 . 109.5 no C7 . C48 . H481 . 105.9 no C7 . C48 . H482 . 112.4 no H481 . C48 . H482 . 109.5 no C7 . C48 . H483 . 110.1 no H481 . C48 . H483 . 109.5 no H482 . C48 . H483 . 109.5 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 . O35 4_656 171 0.94 2.47 3.40(2) yes C14 . H142 . C49 1_545 156 0.97 2.26 3.17(2) yes C15 . H151 . O29 8_646 145 0.98 2.31 3.16(2) yes O123 . H241 . O26 . 122 1.11 2.39 3.12(2) yes O123 . H241 . O126 . 121 1.11 2.14 2.88(2) yes C34 . H342 . C118 8_656 136 0.97 2.56 3.33(2) yes C134 . H342 . C118 8_656 134 1.19 2.56 3.50(2) yes C34 . H341 . O47 4_666 134 0.97 2.58 3.33(2) yes C44 . H442 . O26 4_656 128 0.96 2.53 3.21(2) yes C124 . H1241 . C38 8_646 148 0.97 2.57 3.44(2) yes C19 . H1191 . C124 . 131 0.77 2.59 3.14(2) yes N45 . H451 . O32 4_656 147 0.85 2.43 3.17(2) yes N45 . H451 . O132 4_656 136 0.85 2.17 2.85(2) yes N13 . H131 . O35 4_656 142 0.85 2.56 3.27(2) yes _chemical_name_common . #===END #============================================================================== data_Acetone _database_code_depnum_ccdc_archive 'CCDC 815173' #TrackingRef '- crystallographicdata.cif' #============================================================================== _audit_creation_date 11-01-12 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 5851 _chemical_name_systematic . _chemical_melting_point . _cell_length_a 11.2663(3) _cell_length_b 14.6885(5) _cell_length_c 22.7937(7) _cell_angle_alpha 101.3301(13) _cell_angle_beta 102.2021(14) _cell_angle_gamma 95.3807(12) _cell_volume 3578.74(19) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol 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' _cell_formula_units_Z 4 # Given Formula = C36 H46 N2 O9 S0.50 # Dc = 1.24 Fooo = 1456.00 Mu = 1.16 M = 1333.60 # Found Formula = C37.50 H49 N2 O9.50 # Dc = 1.26 FOOO = 1456.00 Mu = 0.91 M = 1359.62 _chemical_formula_sum 'C37.50 H49 N2 O9.50' _chemical_formula_moiety 'C36 H46 N2 O9, 0.5(C3 H6 O)' _chemical_compound_source ? _chemical_formula_weight 679.81 _cell_measurement_reflns_used 12983 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.030 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_max 0.250 _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.091 # Sheldrick geometric approximatio 0.99 1.00 _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 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 42050 _reflns_number_total 15566 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections without Friedels Law is 25846 # Number of reflections with Friedels Law is 15566 # Theoretical number of reflections is about 11919 _diffrn_reflns_theta_min 5.185 _diffrn_reflns_theta_max 27.642 _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 25.155 _diffrn_measured_fraction_theta_full 0.970 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _reflns_limit_h_min -14 _reflns_limit_h_max 14 _reflns_limit_k_min -19 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 29 _oxford_diffrn_Wilson_B_factor 0.94 _oxford_diffrn_Wilson_scale 23.09 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.29 _refine_diff_density_max 0.35 # 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>2.0\s(I) _refine_ls_number_reflns 6440 _refine_ls_number_restraints 54 _refine_ls_number_parameters 911 _oxford_refine_ls_R_factor_ref 0.0663 _refine_ls_wR_factor_ref 0.0587 _refine_ls_goodness_of_fit_ref 1.0746 _refine_ls_shift/su_max 0.0004712 _refine_ls_shift/su_mean 0.0000191 # The values computed from all data _oxford_reflns_number_all 11601 _refine_ls_R_factor_all 0.1387 _refine_ls_wR_factor_all 0.0938 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6440 _refine_ls_R_factor_gt 0.0663 _refine_ls_wR_factor_gt 0.0587 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment 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: 1.29 1.11 1.33 0.388 0.379 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. 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 C1 C 0.4431(3) 0.3355(2) 0.70330(17) 0.0303 1.0000 Uani . . . . . . . C2 C 0.4900(3) 0.2932(3) 0.65471(17) 0.0322 1.0000 Uani . . . . . . . C3 C 0.4135(4) 0.2259(3) 0.60678(17) 0.0334 1.0000 Uani . . . . . . . C4 C 0.2902(4) 0.1996(3) 0.60598(18) 0.0378 1.0000 Uani . U . . . . . C5 C 0.2459(4) 0.2427(3) 0.65536(17) 0.0339 1.0000 Uani . . . . . . . C6 C 0.3209(3) 0.3105(2) 0.70396(16) 0.0289 1.0000 Uani . . . . . . . C7 C 0.2090(4) 0.1237(3) 0.55409(19) 0.0489 1.0000 Uani . U . . . . . C8 C 0.2669(8) 0.0316(5) 0.5479(3) 0.0621 0.662(9) Uani . U P . 1 . . C9 C 0.1887(10) 0.1540(6) 0.4955(3) 0.0707 0.662(9) Uani . U P . 1 . . C10 C 0.0823(8) 0.0926(7) 0.5683(4) 0.0875 0.662(9) Uani . U P . 1 . . C11 C 0.2658(4) 0.3506(2) 0.75590(18) 0.0317 1.0000 Uani . . . . . . . O12 O 0.1632(3) 0.31747(19) 0.75964(14) 0.0519 1.0000 Uani . . . . . . . N13 N 0.3325(3) 0.4238(2) 0.79828(13) 0.0330 1.0000 Uani . . . . . . . C14 C 0.2887(3) 0.4702(3) 0.85028(16) 0.0329 1.0000 Uani . . . . . . . C15 C 0.3199(4) 0.4243(3) 0.90396(17) 0.0345 1.0000 Uani . . . . . . . O16 O 0.2804(2) 0.48189(17) 0.95233(11) 0.0357 1.0000 Uani . . . . . . . C17 C 0.3183(3) 0.4689(3) 1.01082(17) 0.0316 1.0000 Uani . . . . . . . C18 C 0.3639(3) 0.3900(3) 1.02606(17) 0.0324 1.0000 Uani . . . . . . . C19 C 0.3970(3) 0.3836(3) 1.08734(17) 0.0336 1.0000 Uani . . . . . . . C20 C 0.3858(3) 0.4568(2) 1.13244(16) 0.0275 1.0000 Uani . . . . . . . C21 C 0.3380(3) 0.5360(3) 1.11725(18) 0.0343 1.0000 Uani . . . . . . . C22 C 0.3056(3) 0.5415(3) 1.05721(17) 0.0331 1.0000 Uani . . . . . . . O23 O 0.4211(2) 0.46105(16) 1.19511(11) 0.0344 1.0000 Uani . . . . . . . C24 C 0.4466(4) 0.3766(3) 1.21536(18) 0.0373 1.0000 Uani . . . . . . . C25 C 0.5014(3) 0.4043(3) 1.28260(18) 0.0383 1.0000 Uani . . . . . . . O26 O 0.6249(2) 0.44609(18) 1.29088(11) 0.0346 1.0000 Uani . . . . . . . C27 C 0.6926(4) 0.4651(3) 1.35336(17) 0.0399 1.0000 Uani . . . . . . . C28 C 0.8259(4) 0.4935(3) 1.35619(18) 0.0428 1.0000 Uani . . . . . . . O29 O 0.8802(2) 0.41982(18) 1.32414(11) 0.0377 1.0000 Uani . . . . . . . C30 C 0.8812(4) 0.4264(3) 1.26321(17) 0.0328 1.0000 Uani . . . . . . . C31 C 0.9652(4) 0.3628(3) 1.23984(17) 0.0359 1.0000 Uani . . . . . . . O32 O 0.9745(2) 0.37839(17) 1.18142(11) 0.0336 1.0000 Uani . . . . . . . C33 C 1.0613(4) 0.3281(3) 1.15642(18) 0.0403 1.0000 Uani . . . . . . . C34 C 1.0611(4) 0.3453(3) 1.09410(17) 0.0367 1.0000 Uani . . . . . . . O35 O 0.9576(2) 0.28736(17) 1.05121(11) 0.0349 1.0000 Uani . . . . . . . C36 C 0.9359(3) 0.2981(2) 0.99133(17) 0.0294 1.0000 Uani . . . . . . . C37 C 0.8378(3) 0.2377(2) 0.95044(17) 0.0296 1.0000 Uani . . . . . . . C38 C 0.8063(3) 0.2440(2) 0.88993(17) 0.0297 1.0000 Uani . . . . . . . C39 C 0.8740(3) 0.3102(2) 0.86899(16) 0.0283 1.0000 Uani . . . . . . . C40 C 0.9727(3) 0.3689(2) 0.90925(17) 0.0313 1.0000 Uani . . . . . . . C41 C 1.0032(3) 0.3633(3) 0.97037(17) 0.0330 1.0000 Uani . . . . . . . O42 O 0.8347(2) 0.30911(17) 0.80743(11) 0.0334 1.0000 Uani . . . . . . . C43 C 0.8921(4) 0.3811(3) 0.78444(17) 0.0367 1.0000 Uani . . . . . . . C44 C 0.8332(4) 0.3631(3) 0.71661(18) 0.0472 1.0000 Uani . . . . . . . N45 N 0.7004(3) 0.3592(3) 0.70646(15) 0.0454 1.0000 Uani . . . . . . . C46 C 0.6246(4) 0.3099(3) 0.65445(18) 0.0340 1.0000 Uani . . . . . . . O47 O 0.6615(3) 0.2803(2) 0.60889(13) 0.0576 1.0000 Uani . . . . . . . C48 C 0.1818(16) 0.0450(9) 0.5803(8) 0.0660 0.338(9) Uani . U P . 2 . . C49 C 0.267(2) 0.1025(18) 0.4985(8) 0.1065 0.338(9) Uani . U P . 2 . . C50 C 0.0868(13) 0.1617(10) 0.5314(6) 0.0594 0.338(9) Uani . U P . 2 . . C101 C 1.0620(3) 0.1471(2) 0.29682(17) 0.0308 1.0000 Uani . . . . . . . C102 C 0.9973(3) 0.1897(2) 0.33739(16) 0.0288 1.0000 Uani . . . . . . . C103 C 1.0516(4) 0.2728(2) 0.37987(17) 0.0326 1.0000 Uani . . . . . . . C104 C 1.1735(3) 0.3119(2) 0.38418(16) 0.0289 1.0000 Uani . . . . . . . C105 C 1.2337(3) 0.2682(2) 0.34138(17) 0.0319 1.0000 Uani . . . . . . . C106 C 1.1799(3) 0.1871(2) 0.29718(17) 0.0287 1.0000 Uani . . . . . . . C107 C 1.2333(4) 0.4038(3) 0.43008(17) 0.0350 1.0000 Uani . . . . . . . C108 C 1.2503(7) 0.4802(3) 0.3954(2) 0.0898 1.0000 Uani . . . . . . . C109 C 1.3564(5) 0.3906(4) 0.4676(3) 0.0881 1.0000 Uani . . . . . . . C110 C 1.1546(5) 0.4370(3) 0.4748(2) 0.0618 1.0000 Uani . . . . . . . C111 C 1.2463(3) 0.1500(2) 0.24907(17) 0.0303 1.0000 Uani . . . . . . . O112 O 1.3464(3) 0.18876(19) 0.24758(14) 0.0521 1.0000 Uani . . . . . . . N113 N 1.1860(3) 0.0744(2) 0.20535(13) 0.0326 1.0000 Uani . . . . . . . C114 C 1.2339(4) 0.0308(3) 0.15389(16) 0.0322 1.0000 Uani . . . . . . . C115 C 1.1892(4) 0.0705(3) 0.09838(16) 0.0324 1.0000 Uani . . . . . . . O116 O 1.2214(2) 0.01149(17) 0.04806(11) 0.0340 1.0000 Uani . . . . . . . C117 C 1.1770(3) 0.0270(2) -0.00961(16) 0.0281 1.0000 Uani . . . . . . . C118 C 1.1267(3) 0.1059(3) -0.02062(17) 0.0331 1.0000 Uani . . . . . . . C119 C 1.0880(3) 0.1162(2) -0.08088(17) 0.0303 1.0000 Uani . . . . . . . C120 C 1.0981(3) 0.0472(2) -0.12969(16) 0.0266 1.0000 Uani . . . . . . . C121 C 1.1491(3) -0.0321(2) -0.11768(17) 0.0308 1.0000 Uani . . . . . . . C122 C 1.1887(3) -0.0427(2) -0.05856(17) 0.0290 1.0000 Uani . . . . . . . O123 O 1.0569(2) 0.04854(16) -0.19095(11) 0.0324 1.0000 Uani . . . . . . . C124 C 1.0314(4) 0.1368(2) -0.20551(17) 0.0338 1.0000 Uani . . . . . . . C125 C 0.9795(3) 0.1197(3) -0.27342(17) 0.0346 1.0000 Uani . . . . . . . O126 O 0.8559(2) 0.07350(17) -0.28597(11) 0.0342 1.0000 Uani . . . . . . . C127 C 0.7908(4) 0.0674(3) -0.34706(18) 0.0418 1.0000 Uani . . . . . . . C128 C 0.6616(4) 0.0190(3) -0.35844(19) 0.0421 1.0000 Uani . . . . . . . O129 O 0.5834(3) 0.0721(2) -0.32822(12) 0.0453 1.0000 Uani . . . . . . . C130 C 0.5944(4) 0.0660(3) -0.26612(17) 0.0394 1.0000 Uani . . . . . . . C131 C 0.4927(4) 0.1110(3) -0.24397(18) 0.0414 1.0000 Uani . . . . . . . O132 O 0.5069(2) 0.10627(17) -0.18092(11) 0.0348 1.0000 Uani . . . . . . . C133 C 0.4133(4) 0.1454(3) -0.15516(18) 0.0392 1.0000 Uani . . . . . . . C134 C 0.4267(3) 0.1321(3) -0.09072(17) 0.0368 1.0000 Uani . . . . . . . O135 O 0.5257(2) 0.19913(17) -0.05043(11) 0.0358 1.0000 Uani . . . . . . . C136 C 0.5523(3) 0.1953(2) 0.01074(16) 0.0264 1.0000 Uani . . . . . . . C137 C 0.6465(3) 0.2626(2) 0.04907(17) 0.0311 1.0000 Uani . . . . . . . C138 C 0.6816(3) 0.2642(2) 0.11033(18) 0.0315 1.0000 Uani . . . . . . . C139 C 0.6227(3) 0.2008(2) 0.13651(17) 0.0301 1.0000 Uani . . . . . . . C140 C 0.5270(3) 0.1338(2) 0.09851(17) 0.0323 1.0000 Uani . . . . . . . C141 C 0.4933(3) 0.1309(2) 0.03571(18) 0.0333 1.0000 Uani . . . . . . . O142 O 0.6617(2) 0.21222(17) 0.19954(11) 0.0366 1.0000 Uani . . . . . . . C143 C 0.6178(4) 0.1401(3) 0.22715(18) 0.0368 1.0000 Uani . . . . . . . C144 C 0.6530(3) 0.1768(3) 0.29597(17) 0.0359 1.0000 Uani . . . . . . . N145 N 0.7838(3) 0.2093(2) 0.32017(14) 0.0344 1.0000 Uani . . . . . . . C146 C 0.8658(4) 0.1494(3) 0.32687(18) 0.0354 1.0000 Uani . . . . . . . O147 O 0.8349(3) 0.06446(19) 0.32086(15) 0.0540 1.0000 Uani . . . . . . . O201 O 0.6551(5) 0.3325(3) 0.4488(2) 0.1065 1.0000 Uani . . . . . . . C202 C 0.6794(6) 0.2615(4) 0.4652(2) 0.0675 1.0000 Uani . . . . . . . C203 C 0.8065(7) 0.2539(5) 0.4969(3) 0.0959 1.0000 Uani . . . . . . . C204 C 0.5832(6) 0.1815(4) 0.4564(3) 0.0834 1.0000 Uani . . . . . . . H11 H 0.4938 0.3813 0.7355 0.0374 1.0000 Uiso R . . . . . . H31 H 0.4459 0.1976 0.5745 0.0396 1.0000 Uiso R . . . . . . H51 H 0.1627 0.2253 0.6560 0.0399 1.0000 Uiso R . . . . . . H81 H 0.2164 -0.0153 0.5143 0.0960 0.662(9) Uiso R . P . 1 . . H82 H 0.2755 0.0089 0.5852 0.0959 0.662(9) Uiso R . P . 1 . . H83 H 0.3465 0.0427 0.5398 0.0959 0.662(9) Uiso R . P . 1 . . H91 H 0.1264 0.1098 0.4646 0.1058 0.662(9) Uiso R . P . 1 . . H92 H 0.1620 0.2147 0.5019 0.1061 0.662(9) Uiso R . P . 1 . . H93 H 0.2645 0.1587 0.4823 0.1059 0.662(9) Uiso R . P . 1 . . H101 H 0.0373 0.0396 0.5364 0.1340 0.662(9) Uiso R . P . 1 . . H102 H 0.0946 0.0754 0.6074 0.1340 0.662(9) Uiso R . P . 1 . . H103 H 0.0342 0.1437 0.5692 0.1340 0.662(9) Uiso R . P . 1 . . H142 H 0.3293 0.5338 0.8634 0.0391 1.0000 Uiso R . . . . . . H141 H 0.2016 0.4710 0.8385 0.0385 1.0000 Uiso R . . . . . . H151 H 0.4087 0.4230 0.9156 0.0403 1.0000 Uiso R . . . . . . H152 H 0.2752 0.3609 0.8940 0.0412 1.0000 Uiso R . . . . . . H181 H 0.3717 0.3406 0.9948 0.0392 1.0000 Uiso R . . . . . . H191 H 0.4264 0.3296 1.0978 0.0399 1.0000 Uiso R . . . . . . H211 H 0.3271 0.5847 1.1485 0.0412 1.0000 Uiso R . . . . . . H221 H 0.2753 0.5956 1.0469 0.0390 1.0000 Uiso R . . . . . . H241 H 0.3692 0.3347 1.2069 0.0451 1.0000 Uiso R . . . . . . H242 H 0.5036 0.3462 1.1939 0.0449 1.0000 Uiso R . . . . . . H252 H 0.4551 0.4490 1.3030 0.0456 1.0000 Uiso R . . . . . . H251 H 0.5013 0.3490 1.3007 0.0459 1.0000 Uiso R . . . . . . H271 H 0.6626 0.5161 1.3779 0.0474 1.0000 Uiso R . . . . . . H272 H 0.6825 0.4077 1.3696 0.0480 1.0000 Uiso R . . . . . . H281 H 0.8707 0.5071 1.3992 0.0509 1.0000 Uiso R . . . . . . H282 H 0.8351 0.5490 1.3390 0.0511 1.0000 Uiso R . . . . . . H301 H 0.9102 0.4913 1.2632 0.0393 1.0000 Uiso R . . . . . . H302 H 0.7995 0.4082 1.2369 0.0390 1.0000 Uiso R . . . . . . H311 H 1.0463 0.3755 1.2678 0.0430 1.0000 Uiso R . . . . . . H312 H 0.9313 0.2979 1.2356 0.0432 1.0000 Uiso R . . . . . . H332 H 1.1424 0.3489 1.1841 0.0479 1.0000 Uiso R . . . . . . H331 H 1.0386 0.2614 1.1533 0.0477 1.0000 Uiso R . . . . . . H341 H 1.1346 0.3266 1.0828 0.0440 1.0000 Uiso R . . . . . . H342 H 1.0577 0.4114 1.0938 0.0439 1.0000 Uiso R . . . . . . H371 H 0.7928 0.1932 0.9639 0.0352 1.0000 Uiso R . . . . . . H381 H 0.7395 0.2042 0.8623 0.0347 1.0000 Uiso R . . . . . . H401 H 1.0188 0.4120 0.8951 0.0381 1.0000 Uiso R . . . . . . H411 H 1.0697 0.4037 0.9976 0.0386 1.0000 Uiso R . . . . . . H431 H 0.9796 0.3780 0.7906 0.0438 1.0000 Uiso R . . . . . . H432 H 0.8775 0.4416 0.8057 0.0441 1.0000 Uiso R . . . . . . H442 H 0.8646 0.4132 0.6997 0.0559 1.0000 Uiso R . . . . . . H441 H 0.8529 0.3036 0.6958 0.0562 1.0000 Uiso R . . . . . . H481 H 0.1322 -0.0060 0.5488 0.0949 0.338(9) Uiso R . P . 2 . . H482 H 0.1381 0.0640 0.6116 0.0951 0.338(9) Uiso R . P . 2 . . H483 H 0.2576 0.0249 0.5983 0.0950 0.338(9) Uiso R . P . 2 . . H491 H 0.2061 0.0654 0.4636 0.1559 0.338(9) Uiso R . P . 2 . . H492 H 0.3345 0.0683 0.5078 0.1559 0.338(9) Uiso R . P . 2 . . H493 H 0.2952 0.1603 0.4889 0.1559 0.338(9) Uiso R . P . 2 . . H501 H 0.0301 0.1123 0.5022 0.0840 0.338(9) Uiso R . P . 2 . . H503 H 0.0514 0.1842 0.5652 0.0840 0.338(9) Uiso R . P . 2 . . H502 H 0.1031 0.2119 0.5119 0.0840 0.338(9) Uiso R . P . 2 . . H1011 H 1.0263 0.0915 0.2688 0.0367 1.0000 Uiso R . . . . . . H1031 H 1.0058 0.3030 0.4054 0.0389 1.0000 Uiso R . . . . . . H1051 H 1.3120 0.2942 0.3418 0.0377 1.0000 Uiso R . . . . . . H1081 H 1.2851 0.5391 0.4238 0.1349 1.0000 Uiso R . . . . . . H1083 H 1.3050 0.4647 0.3687 0.1348 1.0000 Uiso R . . . . . . H1082 H 1.1732 0.4875 0.3702 0.1354 1.0000 Uiso R . . . . . . H1091 H 1.3908 0.4495 0.4960 0.1317 1.0000 Uiso R . . . . . . H1093 H 1.4101 0.3732 0.4403 0.1318 1.0000 Uiso R . . . . . . H1092 H 1.3451 0.3428 0.4897 0.1320 1.0000 Uiso R . . . . . . H1101 H 1.1990 0.4942 0.5036 0.0916 1.0000 Uiso R . . . . . . H1103 H 1.1411 0.3889 0.4972 0.0923 1.0000 Uiso R . . . . . . H1102 H 1.0771 0.4500 0.4524 0.0923 1.0000 Uiso R . . . . . . H1141 H 1.3238 0.0397 0.1652 0.0381 1.0000 Uiso R . . . . . . H1142 H 1.2024 -0.0357 0.1441 0.0377 1.0000 Uiso R . . . . . . H1152 H 1.2295 0.1351 0.1051 0.0386 1.0000 Uiso R . . . . . . H1151 H 1.0998 0.0691 0.0908 0.0385 1.0000 Uiso R . . . . . . H1181 H 1.1199 0.1527 0.0125 0.0394 1.0000 Uiso R . . . . . . H1191 H 1.0549 0.1701 -0.0886 0.0362 1.0000 Uiso R . . . . . . H1211 H 1.1555 -0.0783 -0.1508 0.0368 1.0000 Uiso R . . . . . . H1221 H 1.2239 -0.0960 -0.0510 0.0354 1.0000 Uiso R . . . . . . H1242 H 1.1066 0.1812 -0.1932 0.0397 1.0000 Uiso R . . . . . . H1241 H 0.9718 0.1622 -0.1830 0.0398 1.0000 Uiso R . . . . . . H1252 H 1.0273 0.0793 -0.2965 0.0403 1.0000 Uiso R . . . . . . H1251 H 0.9813 0.1797 -0.2858 0.0412 1.0000 Uiso R . . . . . . H1271 H 0.8325 0.0316 -0.3747 0.0501 1.0000 Uiso R . . . . . . H1272 H 0.7900 0.1296 -0.3552 0.0503 1.0000 Uiso R . . . . . . H1282 H 0.6248 0.0083 -0.4025 0.0501 1.0000 Uiso R . . . . . . H1281 H 0.6646 -0.0404 -0.3455 0.0495 1.0000 Uiso R . . . . . . H1301 H 0.6726 0.0985 -0.2415 0.0468 1.0000 Uiso R . . . . . . H1302 H 0.5879 0.0002 -0.2645 0.0476 1.0000 Uiso R . . . . . . H1312 H 0.4979 0.1759 -0.2477 0.0498 1.0000 Uiso R . . . . . . H1311 H 0.4135 0.0769 -0.2679 0.0503 1.0000 Uiso R . . . . . . H1332 H 0.4198 0.2121 -0.1554 0.0466 1.0000 Uiso R . . . . . . H1331 H 0.3331 0.1141 -0.1803 0.0464 1.0000 Uiso R . . . . . . H1341 H 0.4447 0.0685 -0.0891 0.0438 1.0000 Uiso R . . . . . . H1342 H 0.3501 0.1409 -0.0783 0.0445 1.0000 Uiso R . . . . . . H1371 H 0.6856 0.3070 0.0322 0.0361 1.0000 Uiso R . . . . . . H1381 H 0.7462 0.3086 0.1350 0.0376 1.0000 Uiso R . . . . . . H1401 H 0.4856 0.0915 0.1152 0.0388 1.0000 Uiso R . . . . . . H1411 H 0.4303 0.0850 0.0107 0.0395 1.0000 Uiso R . . . . . . H1432 H 0.6539 0.0831 0.2161 0.0438 1.0000 Uiso R . . . . . . H1431 H 0.5283 0.1267 0.2129 0.0436 1.0000 Uiso R . . . . . . H1442 H 0.6287 0.1257 0.3153 0.0431 1.0000 Uiso R . . . . . . H1441 H 0.6087 0.2287 0.3072 0.0428 1.0000 Uiso R . . . . . . H2031 H 0.8279 0.1916 0.4812 0.1455 1.0000 Uiso R . . . . . . H2033 H 0.8150 0.2639 0.5421 0.1454 1.0000 Uiso R . . . . . . H2032 H 0.8609 0.3044 0.4883 0.1456 1.0000 Uiso R . . . . . . H2041 H 0.5879 0.1653 0.4960 0.1249 1.0000 Uiso R . . . . . . H2043 H 0.5040 0.1995 0.4413 0.1254 1.0000 Uiso R . . . . . . H2042 H 0.5988 0.1294 0.4268 0.1248 1.0000 Uiso R . . . . . . H1451 H 0.8105 0.2676 0.3249 0.0413 1.0000 Uiso R . . . . . . H131 H 0.3982 0.4497 0.7923 0.0397 1.0000 Uiso R . . . . . . H1131 H 1.1191 0.0484 0.2099 0.0391 1.0000 Uiso R . . . . . . H451 H 0.6710 0.3750 0.7381 0.0543 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 C1 0.033(2) 0.0259(19) 0.030(2) 0.0037(16) 0.0056(17) 0.0023(16) C2 0.035(2) 0.031(2) 0.031(2) 0.0093(17) 0.0072(18) 0.0032(17) C3 0.042(2) 0.033(2) 0.024(2) 0.0019(16) 0.0103(18) 0.0059(18) C4 0.039(2) 0.035(2) 0.035(2) 0.0023(17) 0.0032(18) 0.0050(17) C5 0.032(2) 0.035(2) 0.032(2) 0.0083(18) 0.0028(18) -0.0027(17) C6 0.032(2) 0.0257(19) 0.027(2) 0.0030(15) 0.0068(17) 0.0034(16) C7 0.052(2) 0.048(2) 0.034(2) -0.0077(17) 0.0017(19) -0.0039(19) C8 0.085(5) 0.039(3) 0.050(5) -0.001(3) 0.003(4) -0.001(3) C9 0.096(8) 0.057(5) 0.041(3) 0.002(3) -0.012(4) 0.006(5) C10 0.063(4) 0.092(7) 0.080(6) -0.029(5) 0.018(4) -0.029(4) C11 0.031(2) 0.0261(19) 0.039(2) 0.0095(17) 0.0094(18) 0.0034(17) O12 0.0426(18) 0.0430(17) 0.064(2) -0.0092(15) 0.0254(16) -0.0100(14) N13 0.0261(17) 0.0339(17) 0.0340(18) -0.0036(14) 0.0111(14) -0.0069(14) C14 0.028(2) 0.036(2) 0.032(2) 0.0035(17) 0.0059(17) 0.0029(17) C15 0.036(2) 0.037(2) 0.030(2) 0.0006(17) 0.0090(18) 0.0114(18) O16 0.0407(16) 0.0414(15) 0.0268(15) 0.0050(12) 0.0101(12) 0.0156(13) C17 0.029(2) 0.035(2) 0.028(2) 0.0046(17) 0.0056(17) 0.0005(17) C18 0.033(2) 0.030(2) 0.035(2) 0.0033(17) 0.0091(18) 0.0088(17) C19 0.033(2) 0.030(2) 0.037(2) 0.0060(17) 0.0040(18) 0.0080(17) C20 0.025(2) 0.031(2) 0.025(2) 0.0043(16) 0.0059(16) 0.0012(16) C21 0.037(2) 0.029(2) 0.037(2) 0.0043(17) 0.0128(18) 0.0046(17) C22 0.035(2) 0.032(2) 0.034(2) 0.0079(17) 0.0079(18) 0.0120(17) O23 0.0391(15) 0.0279(14) 0.0348(16) 0.0077(11) 0.0049(12) 0.0046(12) C24 0.033(2) 0.032(2) 0.047(3) 0.0144(18) 0.0036(19) 0.0044(17) C25 0.033(2) 0.044(2) 0.043(2) 0.0162(19) 0.0141(19) 0.0078(19) O26 0.0337(15) 0.0433(15) 0.0276(14) 0.0102(12) 0.0071(12) 0.0040(12) C27 0.046(3) 0.050(2) 0.022(2) 0.0041(18) 0.0047(18) 0.012(2) C28 0.052(3) 0.041(2) 0.029(2) -0.0012(18) 0.004(2) 0.011(2) O29 0.0472(17) 0.0411(15) 0.0282(14) 0.0093(12) 0.0120(12) 0.0124(13) C30 0.038(2) 0.032(2) 0.029(2) 0.0076(16) 0.0096(17) 0.0041(17) C31 0.036(2) 0.044(2) 0.029(2) 0.0093(18) 0.0061(18) 0.0098(18) O32 0.0362(15) 0.0382(15) 0.0271(14) 0.0082(12) 0.0077(12) 0.0059(12) C33 0.032(2) 0.047(2) 0.041(2) 0.0040(19) 0.0085(19) 0.0152(19) C34 0.032(2) 0.041(2) 0.034(2) 0.0016(18) 0.0086(18) 0.0025(18) O35 0.0319(15) 0.0379(15) 0.0306(15) 0.0035(12) 0.0058(12) -0.0042(12) C36 0.027(2) 0.031(2) 0.032(2) 0.0045(17) 0.0143(17) 0.0036(16) C37 0.028(2) 0.0244(19) 0.037(2) 0.0033(16) 0.0164(18) -0.0020(16) C38 0.026(2) 0.0216(19) 0.036(2) -0.0047(16) 0.0069(17) 0.0002(15) C39 0.029(2) 0.0269(19) 0.028(2) 0.0036(16) 0.0081(17) 0.0050(16) C40 0.028(2) 0.028(2) 0.039(2) 0.0060(17) 0.0131(18) -0.0002(16) C41 0.029(2) 0.034(2) 0.032(2) 0.0014(17) 0.0053(17) -0.0013(17) O42 0.0343(15) 0.0319(14) 0.0321(15) 0.0060(11) 0.0071(12) -0.0007(11) C43 0.028(2) 0.047(2) 0.037(2) 0.0144(19) 0.0075(18) 0.0030(18) C44 0.028(2) 0.078(3) 0.037(2) 0.018(2) 0.0086(19) 0.007(2) N45 0.0282(18) 0.076(3) 0.0292(19) 0.0027(18) 0.0078(15) 0.0091(18) C46 0.040(2) 0.032(2) 0.034(2) 0.0110(17) 0.0131(19) 0.0064(18) O47 0.0474(19) 0.071(2) 0.0443(18) -0.0113(16) 0.0182(15) -0.0072(16) C48 0.069(12) 0.031(5) 0.082(10) 0.000(5) -0.001(8) -0.001(6) C49 0.080(11) 0.141(19) 0.059(9) -0.054(9) 0.028(9) -0.046(11) C50 0.062(6) 0.047(8) 0.042(8) -0.008(6) -0.024(6) -0.007(5) C101 0.034(2) 0.0265(19) 0.031(2) 0.0063(16) 0.0070(17) 0.0026(16) C102 0.029(2) 0.0266(19) 0.031(2) 0.0100(16) 0.0053(17) 0.0021(16) C103 0.038(2) 0.031(2) 0.031(2) 0.0080(16) 0.0103(17) 0.0042(17) C104 0.034(2) 0.0276(19) 0.024(2) 0.0058(15) 0.0050(16) 0.0033(16) C105 0.031(2) 0.029(2) 0.035(2) 0.0068(17) 0.0066(17) 0.0017(17) C106 0.028(2) 0.0255(19) 0.035(2) 0.0081(16) 0.0107(17) 0.0059(16) C107 0.040(2) 0.031(2) 0.032(2) 0.0009(17) 0.0115(18) -0.0006(17) C108 0.174(7) 0.033(3) 0.060(3) -0.003(2) 0.051(4) -0.021(3) C109 0.057(3) 0.063(3) 0.105(5) -0.029(3) -0.025(3) 0.011(3) C110 0.072(3) 0.052(3) 0.049(3) -0.018(2) 0.022(3) -0.008(3) C111 0.029(2) 0.0236(19) 0.040(2) 0.0094(17) 0.0100(18) 0.0027(17) O112 0.0398(17) 0.0355(16) 0.076(2) -0.0079(15) 0.0284(16) -0.0096(14) N113 0.0307(18) 0.0340(17) 0.0313(18) 0.0023(14) 0.0120(14) -0.0042(14) C114 0.037(2) 0.031(2) 0.027(2) 0.0037(16) 0.0082(17) 0.0024(17) C115 0.032(2) 0.034(2) 0.031(2) 0.0007(17) 0.0112(17) 0.0065(17) O116 0.0387(15) 0.0339(14) 0.0314(15) 0.0066(12) 0.0105(12) 0.0113(12) C117 0.025(2) 0.031(2) 0.028(2) 0.0096(16) 0.0036(16) 0.0033(16) C118 0.036(2) 0.033(2) 0.029(2) 0.0019(17) 0.0073(17) 0.0093(18) C119 0.030(2) 0.0272(19) 0.035(2) 0.0060(16) 0.0108(17) 0.0056(16) C120 0.0223(19) 0.029(2) 0.028(2) 0.0061(16) 0.0060(16) 0.0018(15) C121 0.034(2) 0.0243(19) 0.032(2) -0.0015(16) 0.0097(17) 0.0039(16) C122 0.028(2) 0.0251(19) 0.035(2) 0.0049(16) 0.0115(17) 0.0067(16) O123 0.0395(15) 0.0269(13) 0.0301(15) 0.0060(11) 0.0061(12) 0.0056(11) C124 0.031(2) 0.027(2) 0.042(2) 0.0108(17) 0.0051(18) 0.0022(16) C125 0.037(2) 0.030(2) 0.037(2) 0.0102(17) 0.0076(18) 0.0031(17) O126 0.0320(15) 0.0372(15) 0.0314(15) 0.0079(12) 0.0051(12) -0.0004(12) C127 0.046(3) 0.042(2) 0.034(2) 0.0094(18) 0.004(2) 0.004(2) C128 0.037(2) 0.050(3) 0.035(2) 0.0018(19) 0.0082(19) 0.003(2) O129 0.0453(17) 0.0627(19) 0.0342(16) 0.0169(14) 0.0122(13) 0.0193(15) C130 0.043(2) 0.044(2) 0.031(2) 0.0100(18) 0.0067(19) 0.0044(19) C131 0.046(2) 0.048(2) 0.035(2) 0.0148(19) 0.013(2) 0.011(2) O132 0.0340(15) 0.0369(15) 0.0338(15) 0.0076(12) 0.0081(12) 0.0071(12) C133 0.033(2) 0.045(2) 0.037(2) 0.0036(19) 0.0050(18) 0.0108(19) C134 0.028(2) 0.040(2) 0.036(2) 0.0012(18) 0.0040(18) -0.0046(18) O135 0.0362(15) 0.0338(15) 0.0339(16) 0.0047(12) 0.0076(12) -0.0054(12) C136 0.0217(19) 0.0283(19) 0.027(2) 0.0012(15) 0.0061(16) 0.0024(15) C137 0.029(2) 0.026(2) 0.039(2) 0.0056(17) 0.0129(18) 0.0028(16) C138 0.029(2) 0.025(2) 0.040(2) 0.0043(17) 0.0118(18) -0.0002(16) C139 0.029(2) 0.0260(19) 0.036(2) 0.0001(16) 0.0121(17) 0.0074(16) C140 0.031(2) 0.028(2) 0.038(2) 0.0077(17) 0.0088(18) -0.0006(17) C141 0.028(2) 0.027(2) 0.042(2) 0.0014(17) 0.0086(18) -0.0002(16) O142 0.0419(16) 0.0335(14) 0.0304(15) 0.0062(11) 0.0053(12) -0.0057(12) C143 0.034(2) 0.038(2) 0.040(2) 0.0129(18) 0.0096(18) -0.0004(18) C144 0.024(2) 0.048(2) 0.036(2) 0.0071(18) 0.0089(17) 0.0058(18) N145 0.0322(18) 0.0296(17) 0.0401(19) 0.0059(14) 0.0083(15) 0.0026(14) C146 0.035(2) 0.039(2) 0.038(2) 0.0125(18) 0.0174(18) 0.0065(19) O147 0.0448(18) 0.0303(16) 0.090(2) 0.0157(15) 0.0232(16) -0.0006(13) O201 0.165(5) 0.070(3) 0.099(3) 0.039(2) 0.042(3) 0.019(3) C202 0.104(5) 0.057(3) 0.053(3) 0.015(3) 0.036(3) 0.017(3) C203 0.106(5) 0.091(5) 0.101(5) 0.007(4) 0.065(4) 0.008(4) C204 0.112(5) 0.066(4) 0.073(4) 0.007(3) 0.037(4) 0.001(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2425(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 . C2 . 1.390(5) yes C1 . C6 . 1.395(5) yes C1 . H11 . 0.936 no C2 . C3 . 1.390(5) yes C2 . C46 . 1.515(5) yes C3 . C4 . 1.401(5) yes C3 . H31 . 0.933 no C4 . C5 . 1.391(5) yes C4 . C7 . 1.521(5) yes C5 . C6 . 1.395(5) yes C5 . H51 . 0.952 no C6 . C11 . 1.496(5) yes C7 . C8 . 1.550(9) yes C7 . C9 . 1.469(9) yes C7 . C10 . 1.576(9) yes C8 . H81 . 0.960 no C8 . H82 . 0.961 no C8 . H83 . 0.959 no C9 . H91 . 0.968 no C9 . H92 . 0.961 no C9 . H93 . 0.964 no C10 . H101 . 0.969 no C10 . H102 . 0.959 no C10 . H103 . 0.965 no C11 . O12 . 1.238(4) yes C11 . N13 . 1.337(4) yes N13 . C14 . 1.451(5) yes N13 . H131 . 0.849 no C14 . C15 . 1.504(5) yes C14 . H142 . 0.961 no C14 . H141 . 0.964 no C15 . O16 . 1.428(4) yes C15 . H151 . 0.982 no C15 . H152 . 0.977 no O16 . C17 . 1.368(4) yes C17 . C18 . 1.387(5) yes C17 . C22 . 1.387(5) yes C18 . C19 . 1.391(5) yes C18 . H181 . 0.936 no C19 . C20 . 1.369(5) yes C19 . H191 . 0.941 no C20 . C21 . 1.399(5) yes C20 . O23 . 1.387(4) yes C21 . C22 . 1.360(5) yes C21 . H211 . 0.942 no C22 . H221 . 0.945 no O23 . C24 . 1.438(4) yes C24 . C25 . 1.485(5) yes C24 . H241 . 0.979 no C24 . H242 . 0.977 no C25 . O26 . 1.425(4) yes C25 . H252 . 0.983 no C25 . H251 . 0.981 no O26 . C27 . 1.426(4) yes C27 . C28 . 1.504(6) yes C27 . H271 . 0.975 no C27 . H272 . 0.992 no C28 . O29 . 1.443(5) yes C28 . H281 . 0.975 no C28 . H282 . 0.977 no O29 . C30 . 1.413(4) yes C30 . C31 . 1.495(5) yes C30 . H301 . 0.979 no C30 . H302 . 0.968 no C31 . O32 . 1.418(4) yes C31 . H311 . 0.975 no C31 . H312 . 0.972 no O32 . C33 . 1.426(4) yes C33 . C34 . 1.490(5) yes C33 . H332 . 0.977 no C33 . H331 . 0.973 no C34 . O35 . 1.429(4) yes C34 . H341 . 0.967 no C34 . H342 . 0.977 no O35 . C36 . 1.378(4) yes C36 . C37 . 1.391(5) yes C36 . C41 . 1.385(5) yes C37 . C38 . 1.373(5) yes C37 . H371 . 0.928 no C38 . C39 . 1.397(5) yes C38 . H381 . 0.936 no C39 . C40 . 1.379(5) yes C39 . O42 . 1.376(4) yes C40 . C41 . 1.383(5) yes C40 . H401 . 0.930 no C41 . H411 . 0.934 no O42 . C43 . 1.429(4) yes C43 . C44 . 1.508(5) yes C43 . H431 . 0.973 no C43 . H432 . 0.972 no C44 . N45 . 1.459(5) yes C44 . H442 . 0.967 no C44 . H441 . 0.977 no N45 . C46 . 1.333(5) yes N45 . H451 . 0.855 no C46 . O47 . 1.216(4) yes C48 . H481 . 0.963 no C48 . H482 . 0.963 no C48 . H483 . 0.965 no C49 . H491 . 0.962 no C49 . H492 . 0.963 no C49 . H493 . 0.962 no C50 . H501 . 0.959 no C50 . H503 . 0.958 no C50 . H502 . 0.955 no C101 . C102 . 1.386(5) yes C101 . C106 . 1.399(5) yes C101 . H1011 . 0.929 no C102 . C103 . 1.395(5) yes C102 . C146 . 1.494(5) yes C103 . C104 . 1.413(5) yes C103 . H1031 . 0.933 no C104 . C105 . 1.392(5) yes C104 . C107 . 1.532(5) yes C105 . C106 . 1.392(5) yes C105 . H1051 . 0.925 no C106 . C111 . 1.500(5) yes C107 . C108 . 1.515(6) yes C107 . C109 . 1.519(6) yes C107 . C110 . 1.527(6) yes C108 . H1081 . 0.965 no C108 . H1083 . 0.965 no C108 . H1082 . 0.963 no C109 . H1091 . 0.963 no C109 . H1093 . 0.971 no C109 . H1092 . 0.954 no C110 . H1101 . 0.976 no C110 . H1103 . 0.969 no C110 . H1102 . 0.970 no C111 . O112 . 1.225(4) yes C111 . N113 . 1.351(4) yes N113 . C114 . 1.454(5) yes N113 . H1131 . 0.848 no C114 . C115 . 1.507(5) yes C114 . H1141 . 0.980 no C114 . H1142 . 0.973 no C115 . O116 . 1.429(4) yes C115 . H1152 . 0.981 no C115 . H1151 . 0.983 no O116 . C117 . 1.375(4) yes C117 . C118 . 1.380(5) yes C117 . C122 . 1.396(5) yes C118 . C119 . 1.393(5) yes C118 . H1181 . 0.937 no C119 . C120 . 1.382(5) yes C119 . H1191 . 0.938 no C120 . C121 . 1.395(5) yes C120 . O123 . 1.380(4) yes C121 . C122 . 1.371(5) yes C121 . H1211 . 0.930 no C122 . H1221 . 0.939 no O123 . C124 . 1.440(4) yes C124 . C125 . 1.496(5) yes C124 . H1242 . 0.973 no C124 . H1241 . 0.986 no C125 . O126 . 1.435(4) yes C125 . H1252 . 0.988 no C125 . H1251 . 0.978 no O126 . C127 . 1.411(4) yes C127 . C128 . 1.505(5) yes C127 . H1271 . 0.967 no C127 . H1272 . 0.967 no C128 . O129 . 1.426(5) yes C128 . H1282 . 0.977 no C128 . H1281 . 0.976 no O129 . C130 . 1.416(5) yes C130 . C131 . 1.503(6) yes C130 . H1301 . 0.962 no C130 . H1302 . 0.972 no C131 . O132 . 1.428(4) yes C131 . H1312 . 0.972 no C131 . H1311 . 0.973 no O132 . C133 . 1.424(4) yes C133 . C134 . 1.498(5) yes C133 . H1332 . 0.977 no C133 . H1331 . 0.978 no C134 . O135 . 1.437(4) yes C134 . H1341 . 0.980 no C134 . H1342 . 0.975 no O135 . C136 . 1.376(4) yes C136 . C137 . 1.392(5) yes C136 . C141 . 1.384(5) yes C137 . C138 . 1.363(5) yes C137 . H1371 . 0.940 no C138 . C139 . 1.391(5) yes C138 . H1381 . 0.930 no C139 . C140 . 1.397(5) yes C139 . O142 . 1.382(4) yes C140 . C141 . 1.392(5) yes C140 . H1401 . 0.927 no C141 . H1411 . 0.933 no O142 . C143 . 1.434(4) yes C143 . C144 . 1.508(5) yes C143 . H1432 . 0.978 no C143 . H1431 . 0.980 no C144 . N145 . 1.458(5) yes C144 . H1442 . 0.988 no C144 . H1441 . 0.971 no N145 . C146 . 1.340(5) yes N145 . H1451 . 0.858 no C146 . O147 . 1.236(4) yes O201 . C202 . 1.211(6) yes C202 . C203 . 1.487(9) yes C202 . C204 . 1.474(7) yes C203 . H2031 . 0.985 no C203 . H2033 . 0.994 no C203 . H2032 . 0.993 no C204 . H2041 . 0.968 no C204 . H2043 . 0.967 no C204 . H2042 . 0.972 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 C2 . C1 . C6 . 120.4(3) yes C2 . C1 . H11 . 119.6 no C6 . C1 . H11 . 120.0 no C1 . C2 . C3 . 119.0(3) yes C1 . C2 . C46 . 122.8(3) yes C3 . C2 . C46 . 117.8(3) yes C2 . C3 . C4 . 121.9(3) yes C2 . C3 . H31 . 118.5 no C4 . C3 . H31 . 119.6 no C3 . C4 . C5 . 117.8(3) yes C3 . C4 . C7 . 121.1(4) yes C5 . C4 . C7 . 121.1(4) yes C4 . C5 . C6 . 121.4(4) yes C4 . C5 . H51 . 119.2 no C6 . C5 . H51 . 119.4 no C5 . C6 . C1 . 119.5(3) yes C5 . C6 . C11 . 117.4(3) yes C1 . C6 . C11 . 123.1(3) yes C4 . C7 . C8 . 110.4(4) yes C4 . C7 . C9 . 111.0(4) yes C8 . C7 . C9 . 110.2(5) yes C4 . C7 . C10 . 112.4(4) yes C8 . C7 . C10 . 102.4(6) yes C9 . C7 . C10 . 110.1(7) yes C7 . C8 . H81 . 109.8 no C7 . C8 . H82 . 110.9 no H81 . C8 . H82 . 109.4 no C7 . C8 . H83 . 109.7 no H81 . C8 . H83 . 108.4 no H82 . C8 . H83 . 108.7 no C7 . C9 . H91 . 109.9 no C7 . C9 . H92 . 108.3 no H91 . C9 . H92 . 109.6 no C7 . C9 . H93 . 109.5 no H91 . C9 . H93 . 110.2 no H92 . C9 . H93 . 109.2 no C7 . C10 . H101 . 109.8 no C7 . C10 . H102 . 110.7 no H101 . C10 . H102 . 109.3 no C7 . C10 . H103 . 109.6 no H101 . C10 . H103 . 108.6 no H102 . C10 . H103 . 108.8 no C6 . C11 . O12 . 121.6(3) yes C6 . C11 . N13 . 117.0(3) yes O12 . C11 . N13 . 121.4(4) yes C11 . N13 . C14 . 122.5(3) yes C11 . N13 . H131 . 119.6 no C14 . N13 . H131 . 117.3 no N13 . C14 . C15 . 111.4(3) yes N13 . C14 . H142 . 108.4 no C15 . C14 . H142 . 107.3 no N13 . C14 . H141 . 110.5 no C15 . C14 . H141 . 110.5 no H142 . C14 . H141 . 108.7 no C14 . C15 . O16 . 104.7(3) yes C14 . C15 . H151 . 110.4 no O16 . C15 . H151 . 110.7 no C14 . C15 . H152 . 110.5 no O16 . C15 . H152 . 110.0 no H151 . C15 . H152 . 110.5 no C15 . O16 . C17 . 118.2(3) yes O16 . C17 . C18 . 125.4(3) yes O16 . C17 . C22 . 115.1(3) yes C18 . C17 . C22 . 119.4(3) yes C17 . C18 . C19 . 120.4(3) yes C17 . C18 . H181 . 119.6 no C19 . C18 . H181 . 120.0 no C18 . C19 . C20 . 119.2(4) yes C18 . C19 . H191 . 120.6 no C20 . C19 . H191 . 120.2 no C19 . C20 . C21 . 120.6(3) yes C19 . C20 . O23 . 124.8(3) yes C21 . C20 . O23 . 114.6(3) yes C20 . C21 . C22 . 119.7(3) yes C20 . C21 . H211 . 120.1 no C22 . C21 . H211 . 120.2 no C17 . C22 . C21 . 120.6(4) yes C17 . C22 . H221 . 119.5 no C21 . C22 . H221 . 119.8 no C20 . O23 . C24 . 118.7(3) yes O23 . C24 . C25 . 107.0(3) yes O23 . C24 . H241 . 108.5 no C25 . C24 . H241 . 110.5 no O23 . C24 . H242 . 110.3 no C25 . C24 . H242 . 110.4 no H241 . C24 . H242 . 110.2 no C24 . C25 . O26 . 107.5(3) yes C24 . C25 . H252 . 110.6 no O26 . C25 . H252 . 110.4 no C24 . C25 . H251 . 110.3 no O26 . C25 . H251 . 109.1 no H252 . C25 . H251 . 109.0 no C25 . O26 . C27 . 112.9(3) yes O26 . C27 . C28 . 109.1(3) yes O26 . C27 . H271 . 109.9 no C28 . C27 . H271 . 109.1 no O26 . C27 . H272 . 108.9 no C28 . C27 . H272 . 110.1 no H271 . C27 . H272 . 109.7 no C27 . C28 . O29 . 113.0(3) yes C27 . C28 . H281 . 108.2 no O29 . C28 . H281 . 106.3 no C27 . C28 . H282 . 109.7 no O29 . C28 . H282 . 109.4 no H281 . C28 . H282 . 110.2 no C28 . O29 . C30 . 113.5(3) yes O29 . C30 . C31 . 109.0(3) yes O29 . C30 . H301 . 108.9 no C31 . C30 . H301 . 110.0 no O29 . C30 . H302 . 110.3 no C31 . C30 . H302 . 109.5 no H301 . C30 . H302 . 109.1 no C30 . C31 . O32 . 107.6(3) yes C30 . C31 . H311 . 111.1 no O32 . C31 . H311 . 109.9 no C30 . C31 . H312 . 109.7 no O32 . C31 . H312 . 109.6 no H311 . C31 . H312 . 108.8 no C31 . O32 . C33 . 113.2(3) yes O32 . C33 . C34 . 109.6(3) yes O32 . C33 . H332 . 108.8 no C34 . C33 . H332 . 110.6 no O32 . C33 . H331 . 108.9 no C34 . C33 . H331 . 109.6 no H332 . C33 . H331 . 109.3 no C33 . C34 . O35 . 108.2(3) yes C33 . C34 . H341 . 108.6 no O35 . C34 . H341 . 108.2 no C33 . C34 . H342 . 110.8 no O35 . C34 . H342 . 110.8 no H341 . C34 . H342 . 110.1 no C34 . O35 . C36 . 117.1(3) yes O35 . C36 . C37 . 115.4(3) yes O35 . C36 . C41 . 125.0(3) yes C37 . C36 . C41 . 119.6(3) yes C36 . C37 . C38 . 120.2(3) yes C36 . C37 . H371 . 120.3 no C38 . C37 . H371 . 119.5 no C37 . C38 . C39 . 120.1(3) yes C37 . C38 . H381 . 120.6 no C39 . C38 . H381 . 119.3 no C38 . C39 . C40 . 119.7(3) yes C38 . C39 . O42 . 114.8(3) yes C40 . C39 . O42 . 125.4(3) yes C39 . C40 . C41 . 120.1(3) yes C39 . C40 . H401 . 119.7 no C41 . C40 . H401 . 120.2 no C36 . C41 . C40 . 120.3(3) yes C36 . C41 . H411 . 119.9 no C40 . C41 . H411 . 119.8 no C39 . O42 . C43 . 117.6(3) yes O42 . C43 . C44 . 106.6(3) yes O42 . C43 . H431 . 110.1 no C44 . C43 . H431 . 110.0 no O42 . C43 . H432 . 108.8 no C44 . C43 . H432 . 110.6 no H431 . C43 . H432 . 110.6 no C43 . C44 . N45 . 110.6(3) yes C43 . C44 . H442 . 109.5 no N45 . C44 . H442 . 108.7 no C43 . C44 . H441 . 109.2 no N45 . C44 . H441 . 109.6 no H442 . C44 . H441 . 109.3 no C44 . N45 . C46 . 121.7(3) yes C44 . N45 . H451 . 117.5 no C46 . N45 . H451 . 118.3 no C2 . C46 . N45 . 116.7(3) yes C2 . C46 . O47 . 121.6(4) yes N45 . C46 . O47 . 121.7(4) yes C7 . C48 . H481 . 110.1 no C7 . C48 . H482 . 108.9 no H481 . C48 . H482 . 109.7 no C7 . C48 . H483 . 109.2 no H481 . C48 . H483 . 109.4 no H482 . C48 . H483 . 109.6 no C7 . C49 . H491 . 109.5 no C7 . C49 . H492 . 109.8 no H491 . C49 . H492 . 109.3 no C7 . C49 . H493 . 109.5 no H491 . C49 . H493 . 109.3 no H492 . C49 . H493 . 109.4 no C7 . C50 . H501 . 109.4 no C7 . C50 . H503 . 110.7 no H501 . C50 . H503 . 109.4 no C7 . C50 . H502 . 109.1 no H501 . C50 . H502 . 109.2 no H503 . C50 . H502 . 109.0 no C102 . C101 . C106 . 121.0(3) yes C102 . C101 . H1011 . 119.6 no C106 . C101 . H1011 . 119.5 no C101 . C102 . C103 . 119.4(3) yes C101 . C102 . C146 . 116.5(3) yes C103 . C102 . C146 . 123.6(3) yes C102 . C103 . C104 . 121.2(3) yes C102 . C103 . H1031 . 118.9 no C104 . C103 . H1031 . 119.9 no C103 . C104 . C105 . 117.4(3) yes C103 . C104 . C107 . 121.5(3) yes C105 . C104 . C107 . 120.9(3) yes C104 . C105 . C106 . 122.4(3) yes C104 . C105 . H1051 . 119.2 no C106 . C105 . H1051 . 118.3 no C101 . C106 . C105 . 118.5(3) yes C101 . C106 . C111 . 122.5(3) yes C105 . C106 . C111 . 118.9(3) yes C104 . C107 . C108 . 109.4(3) yes C104 . C107 . C109 . 109.9(3) yes C108 . C107 . C109 . 110.1(5) yes C104 . C107 . C110 . 112.4(3) yes C108 . C107 . C110 . 107.1(4) yes C109 . C107 . C110 . 107.9(4) yes C107 . C108 . H1081 . 110.4 no C107 . C108 . H1083 . 110.4 no H1081 . C108 . H1083 . 108.3 no C107 . C108 . H1082 . 110.9 no H1081 . C108 . H1082 . 109.0 no H1083 . C108 . H1082 . 107.8 no C107 . C109 . H1091 . 107.4 no C107 . C109 . H1093 . 109.5 no H1091 . C109 . H1093 . 110.1 no C107 . C109 . H1092 . 109.8 no H1091 . C109 . H1092 . 110.1 no H1093 . C109 . H1092 . 109.9 no C107 . C110 . H1101 . 108.2 no C107 . C110 . H1103 . 108.9 no H1101 . C110 . H1103 . 109.5 no C107 . C110 . H1102 . 110.0 no H1101 . C110 . H1102 . 109.6 no H1103 . C110 . H1102 . 110.5 no C106 . C111 . O112 . 122.0(3) yes C106 . C111 . N113 . 116.0(3) yes O112 . C111 . N113 . 121.9(4) yes C111 . N113 . C114 . 123.8(3) yes C111 . N113 . H1131 . 117.8 no C114 . N113 . H1131 . 118.3 no N113 . C114 . C115 . 110.7(3) yes N113 . C114 . H1141 . 110.5 no C115 . C114 . H1141 . 110.1 no N113 . C114 . H1142 . 106.8 no C115 . C114 . H1142 . 108.7 no H1141 . C114 . H1142 . 110.0 no C114 . C115 . O116 . 106.0(3) yes C114 . C115 . H1152 . 110.0 no O116 . C115 . H1152 . 110.5 no C114 . C115 . H1151 . 109.5 no O116 . C115 . H1151 . 110.7 no H1152 . C115 . H1151 . 110.1 no C115 . O116 . C117 . 116.9(3) yes O116 . C117 . C118 . 124.3(3) yes O116 . C117 . C122 . 115.3(3) yes C118 . C117 . C122 . 120.3(3) yes C117 . C118 . C119 . 119.8(3) yes C117 . C118 . H1181 . 119.9 no C119 . C118 . H1181 . 120.3 no C118 . C119 . C120 . 120.3(3) yes C118 . C119 . H1191 . 120.2 no C120 . C119 . H1191 . 119.5 no C119 . C120 . C121 . 119.1(3) yes C119 . C120 . O123 . 124.7(3) yes C121 . C120 . O123 . 116.1(3) yes C120 . C121 . C122 . 121.2(3) yes C120 . C121 . H1211 . 118.5 no C122 . C121 . H1211 . 120.2 no C117 . C122 . C121 . 119.3(3) yes C117 . C122 . H1221 . 120.3 no C121 . C122 . H1221 . 120.4 no C120 . O123 . C124 . 117.6(3) yes O123 . C124 . C125 . 107.9(3) yes O123 . C124 . H1242 . 109.6 no C125 . C124 . H1242 . 110.7 no O123 . C124 . H1241 . 109.6 no C125 . C124 . H1241 . 110.2 no H1242 . C124 . H1241 . 108.8 no C124 . C125 . O126 . 107.5(3) yes C124 . C125 . H1252 . 111.2 no O126 . C125 . H1252 . 109.2 no C124 . C125 . H1251 . 109.1 no O126 . C125 . H1251 . 110.9 no H1252 . C125 . H1251 . 108.9 no C125 . O126 . C127 . 112.5(3) yes O126 . C127 . C128 . 111.0(3) yes O126 . C127 . H1271 . 108.5 no C128 . C127 . H1271 . 108.8 no O126 . C127 . H1272 . 109.7 no C128 . C127 . H1272 . 110.2 no H1271 . C127 . H1272 . 108.6 no C127 . C128 . O129 . 114.7(3) yes C127 . C128 . H1282 . 107.7 no O129 . C128 . H1282 . 106.0 no C127 . C128 . H1281 . 108.6 no O129 . C128 . H1281 . 109.2 no H1282 . C128 . H1281 . 110.7 no C128 . O129 . C130 . 114.0(3) yes O129 . C130 . C131 . 107.8(3) yes O129 . C130 . H1301 . 109.8 no C131 . C130 . H1301 . 109.9 no O129 . C130 . H1302 . 108.3 no C131 . C130 . H1302 . 111.2 no H1301 . C130 . H1302 . 109.8 no C130 . C131 . O132 . 107.1(3) yes C130 . C131 . H1312 . 110.3 no O132 . C131 . H1312 . 110.2 no C130 . C131 . H1311 . 110.0 no O132 . C131 . H1311 . 109.7 no H1312 . C131 . H1311 . 109.5 no C131 . O132 . C133 . 112.1(3) yes O132 . C133 . C134 . 110.0(3) yes O132 . C133 . H1332 . 109.0 no C134 . C133 . H1332 . 110.3 no O132 . C133 . H1331 . 109.2 no C134 . C133 . H1331 . 109.6 no H1332 . C133 . H1331 . 108.8 no C133 . C134 . O135 . 109.2(3) yes C133 . C134 . H1341 . 109.5 no O135 . C134 . H1341 . 109.5 no C133 . C134 . H1342 . 109.0 no O135 . C134 . H1342 . 110.3 no H1341 . C134 . H1342 . 109.4 no C134 . O135 . C136 . 116.8(3) yes O135 . C136 . C137 . 115.6(3) yes O135 . C136 . C141 . 125.2(3) yes C137 . C136 . C141 . 119.2(3) yes C136 . C137 . C138 . 120.5(3) yes C136 . C137 . H1371 . 119.2 no C138 . C137 . H1371 . 120.3 no C137 . C138 . C139 . 121.2(3) yes C137 . C138 . H1381 . 119.2 no C139 . C138 . H1381 . 119.6 no C138 . C139 . C140 . 118.7(4) yes C138 . C139 . O142 . 116.1(3) yes C140 . C139 . O142 . 125.2(3) yes C139 . C140 . C141 . 120.0(3) yes C139 . C140 . H1401 . 120.0 no C141 . C140 . H1401 . 120.0 no C140 . C141 . C136 . 120.4(3) yes C140 . C141 . H1411 . 119.1 no C136 . C141 . H1411 . 120.5 no C139 . O142 . C143 . 118.0(3) yes O142 . C143 . C144 . 107.7(3) yes O142 . C143 . H1432 . 110.8 no C144 . C143 . H1432 . 110.0 no O142 . C143 . H1431 . 108.8 no C144 . C143 . H1431 . 109.8 no H1432 . C143 . H1431 . 109.8 no C143 . C144 . N145 . 113.4(3) yes C143 . C144 . H1442 . 108.0 no N145 . C144 . H1442 . 108.9 no C143 . C144 . H1441 . 109.7 no N145 . C144 . H1441 . 108.2 no H1442 . C144 . H1441 . 108.5 no C144 . N145 . C146 . 121.9(3) yes C144 . N145 . H1451 . 119.1 no C146 . N145 . H1451 . 118.3 no C102 . C146 . N145 . 116.2(3) yes C102 . C146 . O147 . 121.3(4) yes N145 . C146 . O147 . 122.3(4) yes O201 . C202 . C203 . 120.9(6) yes O201 . C202 . C204 . 121.1(6) yes C203 . C202 . C204 . 118.0(5) yes C202 . C203 . H2031 . 110.3 no C202 . C203 . H2033 . 110.7 no H2031 . C203 . H2033 . 109.4 no C202 . C203 . H2032 . 106.4 no H2031 . C203 . H2032 . 111.1 no H2033 . C203 . H2032 . 109.0 no C202 . C204 . H2041 . 107.6 no C202 . C204 . H2043 . 109.1 no H2041 . C204 . H2043 . 110.7 no C202 . C204 . H2042 . 108.3 no H2041 . C204 . H2042 . 110.7 no H2043 . C204 . H2042 . 110.3 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 . O23 2_667 160 0.94 2.51 3.400(7) yes C24 . H241 . O112 1_456 124 0.98 2.51 3.161(7) yes C27 . H272 . O201 1_556 151 0.99 2.35 3.257(7) yes C43 . H431 . O12 1_655 153 0.97 2.51 3.403(7) yes C101 . H1011 . O123 2_755 176 0.93 2.40 3.327(7) yes C124 . H1242 . O12 1_654 128 0.97 2.54 3.235(7) yes C138 . H1381 . O32 1_554 155 0.93 2.59 3.458(7) yes C143 . H1431 . O112 1_455 136 0.98 2.53 3.310(7) yes C203 . H2033 . O47 . 133 0.99 2.53 3.292(7) yes N145 . H1451 . O29 1_554 173 0.86 2.30 3.157(7) yes N13 . H131 . O23 2_667 164 0.85 2.25 3.071(7) yes N113 . H1131 . O123 2_755 161 0.85 2.24 3.053(7) yes _chemical_name_common . #===END #============================================================================== data_MeCN _database_code_depnum_ccdc_archive 'CCDC 815174' #TrackingRef '- crystallographicdata.cif' #============================================================================== _audit_creation_date 11-01-20 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 033CJS08 _chemical_name_systematic . _chemical_melting_point . # start Validation Reply Form _vrf_DIFMN02_MeCN ; PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00 RESPONSE: Some minor disorder was identified in the polyether portion between O(123) and O(129). Attempts to model this using partial occupancies led to an unstable model requiring excessive restraining. It was therefore considered better to leave the small remaining electron density unmodelled. ; _vrf_DIFMX01_MeCN ; PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00 RESPONSE: Some minor disorder was identified in the polyether portion between O(123) and O(129). Attempts to model this using partial occupancies led to an unstable model requiring excessive restraining. It was therefore considered better to leave the small remaining electron density unmodelled. ; _vrf_PLAT097_MeCN ; PROBLEM: Large Reported Max. (Positive) Residual Density 1.40 eA-3 RESPONSE: Some minor disorder was identified in the polyether portion between O(123) and O(129). Attempts to model this using partial occupancies led to an unstable model requiring excessive restraining. It was therefore considered better to leave the small remaining electron density unmodelled. ; _vrf_PLAT098_MeCN ; PROBLEM: Large Reported Min. (Negative) Residual Density -0.77 eA-3 RESPONSE: Some minor disorder was identified in the polyether portion between O(123) and O(129). Attempts to model this using partial occupancies led to an unstable model requiring excessive restraining. It was therefore considered better to leave the small remaining electron density unmodelled. ; # end Validation Reply Form _cell_length_a 13.56390(10) _cell_length_b 16.22440(10) _cell_length_c 19.8583(2) _cell_angle_alpha 102.6195(4) _cell_angle_beta 92.0868(4) _cell_angle_gamma 113.4947(4) _cell_volume 3873.60(6) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol 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' _cell_formula_units_Z 4 # Given Formula = C33 N6 O13 # Dc = 1.18 Fooo = 1546.00 Mu = 0.95 M = 1376.79 # Found Formula = C39.50 H51.25 N3.75 O9 # Dc = 1.24 FOOO = 1546.00 Mu = 0.88 M = 1445.22 _chemical_formula_sum 'C39.50 H51.25 N3.75 O9' _chemical_formula_moiety 'C36 H46 N2 O9, 1.75(C2 H3 N)' _chemical_compound_source . _chemical_formula_weight 722.61 _cell_measurement_reflns_used 16883 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.500 _exptl_crystal_size_mid 0.510 _exptl_crystal_size_max 0.520 _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1546.000 _exptl_absorpt_coefficient_mu 0.088 # Sheldrick geometric approximatio 0.96 0.96 _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 0.96 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 76597 _reflns_number_total 17567 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections without Friedels Law is 31896 # Number of reflections with Friedels Law is 17567 # Theoretical number of reflections is about 15167 _diffrn_reflns_theta_min 5.127 _diffrn_reflns_theta_max 27.484 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.384 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -17 _reflns_limit_h_max 17 _reflns_limit_k_min -21 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _oxford_diffrn_Wilson_B_factor 2.68 _oxford_diffrn_Wilson_scale 1.77 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.77 _refine_diff_density_max 1.40 # 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 14981 _refine_ls_number_restraints 54 _refine_ls_number_parameters 983 _oxford_refine_ls_R_factor_ref 0.0661 _refine_ls_wR_factor_ref 0.1439 _refine_ls_goodness_of_fit_ref 0.9236 _refine_ls_shift/su_max 0.0004277 _refine_ls_shift/su_mean 0.0000332 # The values computed from all data _oxford_reflns_number_all 14987 _refine_ls_R_factor_all 0.0661 _refine_ls_wR_factor_all 0.1441 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 12736 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_gt 0.1368 # 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: 79.9 128. 73.8 29.3 6.59 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. 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 C1 C 1.09426(14) 0.64004(12) 0.46634(9) 0.0268 1.0000 Uani . . . . . . . C2 C 1.02067(14) 0.65382(12) 0.50878(9) 0.0263 1.0000 Uani . . . . . . . C3 C 1.03294(14) 0.65325(13) 0.57878(9) 0.0275 1.0000 Uani . . . . . . . C4 C 1.11905(14) 0.63939(13) 0.60732(9) 0.0275 1.0000 Uani . U . . . . . C5 C 1.19048(14) 0.62336(13) 0.56280(9) 0.0273 1.0000 Uani . . . . . . . C6 C 1.17899(14) 0.62321(12) 0.49285(9) 0.0257 1.0000 Uani . . . . . . . C7 C 1.13604(16) 0.64108(15) 0.68438(10) 0.0355 1.0000 Uani . U . . . . . C8 C 1.1355(3) 0.5441(2) 0.68775(16) 0.0453 0.723(4) Uani . U P 1 1 . . C9 C 1.0491(3) 0.6526(3) 0.72391(16) 0.0478 0.723(4) Uani . U P 1 1 . . C10 C 1.2480(3) 0.7148(2) 0.71781(16) 0.0452 0.723(4) Uani . U P 1 1 . . C11 C 1.25346(14) 0.60709(13) 0.44285(9) 0.0273 1.0000 Uani . . . . . . . O12 O 1.26405(12) 0.63696(11) 0.39042(7) 0.0388 1.0000 Uani . . . . . . . N13 N 1.30624(12) 0.55681(11) 0.45762(8) 0.0282 1.0000 Uani . . . . . . . C14 C 1.37705(15) 0.53314(13) 0.41118(10) 0.0304 1.0000 Uani . . . . . . . C15 C 1.31499(15) 0.46019(13) 0.34510(9) 0.0297 1.0000 Uani . . . . . . . O16 O 1.24641(11) 0.37724(9) 0.36370(7) 0.0328 1.0000 Uani . . . . . . . C17 C 1.18783(15) 0.30055(13) 0.30929(9) 0.0296 1.0000 Uani . . . . . . . C18 C 1.13013(16) 0.21815(14) 0.32806(10) 0.0332 1.0000 Uani . . . . . . . C19 C 1.06584(17) 0.13885(14) 0.27793(10) 0.0351 1.0000 Uani . . . . . . . C20 C 1.05747(16) 0.14023(14) 0.20799(10) 0.0327 1.0000 Uani . . . . . . . C21 C 1.11791(16) 0.22098(14) 0.18890(10) 0.0332 1.0000 Uani . . . . . . . C22 C 1.18331(15) 0.30118(14) 0.23963(10) 0.0322 1.0000 Uani . . . . . . . O23 O 0.98972(13) 0.05801(10) 0.16205(7) 0.0409 1.0000 Uani . . . . . . . C24 C 0.95538(19) 0.06307(16) 0.09458(11) 0.0430 1.0000 Uani . . . . . . . C25 C 0.8576(2) -0.02524(16) 0.06275(11) 0.0450 1.0000 Uani . . . . . . . O26 O 0.77207(13) -0.02819(10) 0.10294(8) 0.0448 1.0000 Uani . . . . . . . C27 C 0.6725(2) -0.10160(16) 0.07142(15) 0.0565 1.0000 Uani . . . . . . . C28 C 0.5894(2) -0.10866(17) 0.11919(17) 0.0594 1.0000 Uani . . . . . . . O29 O 0.56768(15) -0.02887(12) 0.12942(10) 0.0571 1.0000 Uani . . . . . . . C30 C 0.4890(3) -0.0301(2) 0.17429(18) 0.0675 1.0000 Uani . . . . . . . C31 C 0.4830(3) 0.0629(2) 0.18875(15) 0.0622 1.0000 Uani . . . . . . . O32 O 0.44183(15) 0.07329(12) 0.12620(9) 0.0538 1.0000 Uani . . . . . . . C33 C 0.4527(2) 0.16519(16) 0.12942(11) 0.0459 1.0000 Uani . . . . . . . C34 C 0.35977(18) 0.18367(15) 0.15709(11) 0.0408 1.0000 Uani . . . . . . . O35 O 0.36060(12) 0.19224(10) 0.23086(7) 0.0373 1.0000 Uani . . . . . . . C36 C 0.43029(15) 0.27555(13) 0.27490(10) 0.0314 1.0000 Uani . . . . . . . C37 C 0.42517(15) 0.28149(14) 0.34572(10) 0.0326 1.0000 Uani . . . . . . . C38 C 0.49314(15) 0.36012(14) 0.39513(10) 0.0317 1.0000 Uani . . . . . . . C39 C 0.56636(14) 0.43647(13) 0.37474(9) 0.0288 1.0000 Uani . . . . . . . C40 C 0.56974(15) 0.43192(14) 0.30451(10) 0.0317 1.0000 Uani . . . . . . . C41 C 0.50222(16) 0.35133(14) 0.25445(10) 0.0332 1.0000 Uani . . . . . . . O42 O 0.63148(11) 0.51195(9) 0.42820(7) 0.0324 1.0000 Uani . . . . . . . C43 C 0.68825(15) 0.59887(13) 0.41053(10) 0.0299 1.0000 Uani . . . . . . . C44 C 0.75147(15) 0.67013(14) 0.47679(10) 0.0309 1.0000 Uani . . . . . . . N45 N 0.84006(12) 0.65176(11) 0.50443(8) 0.0285 1.0000 Uani . . . . . . . C46 C 0.93222(15) 0.67200(14) 0.47573(9) 0.0298 1.0000 Uani . . . . . . . O47 O 0.94462(12) 0.70314(13) 0.42402(8) 0.0467 1.0000 Uani . . . . . . . C48 C 1.0329(7) 0.5783(10) 0.7046(5) 0.0603 0.277(4) Uani . U P 1 2 . . C49 C 1.1496(10) 0.7500(8) 0.7285(4) 0.0614 0.277(4) Uani . U P 1 2 . . C50 C 1.2328(7) 0.6367(7) 0.7101(4) 0.0470 0.277(4) Uani . U P 1 2 . . C101 C 1.46808(14) 0.36745(12) 0.03817(9) 0.0263 1.0000 Uani . . . . . . . C102 C 1.38132(14) 0.34594(12) -0.01148(9) 0.0248 1.0000 Uani . . . . . . . C103 C 1.39907(14) 0.35240(12) -0.07952(9) 0.0270 1.0000 Uani . . . . . . . C104 C 1.50366(14) 0.37978(12) -0.09810(9) 0.0265 1.0000 Uani . . . . . . . C105 C 1.58990(14) 0.40391(13) -0.04633(9) 0.0280 1.0000 Uani . . . . . . . C106 C 1.57341(14) 0.39908(13) 0.02165(9) 0.0270 1.0000 Uani . . . . . . . C107 C 1.52624(15) 0.38277(14) -0.17309(9) 0.0312 1.0000 Uani . . . . . . . C108 C 1.60933(18) 0.48004(15) -0.17333(11) 0.0402 1.0000 Uani . . . . . . . C109 C 1.42384(18) 0.3592(2) -0.22174(11) 0.0509 1.0000 Uani . . . . . . . C110 C 1.57409(19) 0.31257(15) -0.20101(11) 0.0418 1.0000 Uani . . . . . . . C111 C 1.66282(15) 0.42853(14) 0.08093(10) 0.0321 1.0000 Uani . . . . . . . O112 O 1.64296(11) 0.40527(12) 0.13545(8) 0.0471 1.0000 Uani . . . . . . . N113 N 1.76341(12) 0.48412(12) 0.07264(8) 0.0329 1.0000 Uani . . . . . . . C114 C 1.85549(15) 0.51471(16) 0.12681(11) 0.0381 1.0000 Uani . . . . . . . C115 C 1.85599(16) 0.58698(15) 0.18907(11) 0.0382 1.0000 Uani . . . . . . . O116 O 1.86869(12) 0.66867(11) 0.16694(7) 0.0417 1.0000 Uani . . . . . . . C117 C 1.86306(16) 0.74149(15) 0.21578(11) 0.0387 1.0000 Uani . . . . . . . C118 C 1.85765(18) 0.81353(16) 0.19070(11) 0.0447 1.0000 Uani . . . . . . . C119 C 1.8455(2) 0.88702(16) 0.23453(12) 0.0511 1.0000 Uani . . . . . . . C120 C 1.8403(2) 0.89027(17) 0.30488(13) 0.0546 1.0000 Uani . . . . . . . C121 C 1.8495(2) 0.81987(17) 0.32995(12) 0.0540 1.0000 Uani . . . . . . . C122 C 1.86098(18) 0.74578(17) 0.28632(11) 0.0456 1.0000 Uani . . . . . . . O123 O 1.8292(2) 0.96073(14) 0.35219(10) 0.0801 1.0000 Uani . . . . . . . C124 C 1.7880(3) 1.0175(2) 0.32861(17) 0.0695 1.0000 Uani . . . . . . . C125 C 1.7823(3) 1.0875(3) 0.3905(2) 0.0812 1.0000 Uani . . . . . . . O126 O 1.69563(17) 1.04774(13) 0.42284(13) 0.0787 1.0000 Uani . . . . . . . C127 C 1.6715(2) 1.11265(19) 0.47220(18) 0.0709 1.0000 Uani . . . . . . . C128 C 1.5895(2) 1.14059(17) 0.44173(15) 0.0592 1.0000 Uani . . . . . . . O129 O 1.48437(14) 1.06672(11) 0.43312(9) 0.0498 1.0000 Uani . . . . . . . C130 C 1.4044(2) 1.08661(17) 0.40168(13) 0.0544 1.0000 Uani . . . . . . . C131 C 1.2927(2) 1.01807(17) 0.40543(13) 0.0511 1.0000 Uani . . . . . . . O132 O 1.27333(13) 0.92857(11) 0.36343(8) 0.0468 1.0000 Uani . . . . . . . C133 C 1.16520(19) 0.86280(17) 0.36173(12) 0.0448 1.0000 Uani . . . . . . . C134 C 1.15196(18) 0.76934(15) 0.32062(10) 0.0387 1.0000 Uani . . . . . . . O135 O 1.15906(13) 0.77137(10) 0.24918(7) 0.0407 1.0000 Uani . . . . . . . C136 C 1.14837(15) 0.69096(14) 0.20314(10) 0.0340 1.0000 Uani . . . . . . . C137 C 1.15200(16) 0.69349(14) 0.13320(11) 0.0350 1.0000 Uani . . . . . . . C138 C 1.14149(15) 0.61632(14) 0.08285(10) 0.0339 1.0000 Uani . . . . . . . C139 C 1.12583(14) 0.53382(14) 0.10100(10) 0.0313 1.0000 Uani . . . . . . . C140 C 1.12202(15) 0.53101(14) 0.17012(10) 0.0339 1.0000 Uani . . . . . . . C141 C 1.13373(16) 0.60933(15) 0.22114(10) 0.0347 1.0000 Uani . . . . . . . O142 O 1.11741(11) 0.46025(10) 0.04687(7) 0.0347 1.0000 Uani . . . . . . . C143 C 1.08515(15) 0.37082(13) 0.06187(10) 0.0326 1.0000 Uani . . . . . . . C144 C 1.08544(14) 0.30299(14) -0.00330(10) 0.0333 1.0000 Uani . . . . . . . N145 N 1.19402(12) 0.32705(11) -0.02367(8) 0.0295 1.0000 Uani . . . . . . . C146 C 1.27111(14) 0.31502(12) 0.01210(9) 0.0267 1.0000 Uani . . . . . . . O147 O 1.25371(11) 0.28213(11) 0.06285(7) 0.0381 1.0000 Uani . . . . . . . C201 C 0.1626(2) -0.03603(18) 0.20875(14) 0.0553 1.0000 Uani . . . . . . . C202 C 0.1402(2) -0.06398(16) 0.13333(15) 0.0530 1.0000 Uani . . . . . . . N203 N 0.1223(2) -0.08605(18) 0.07422(14) 0.0781 1.0000 Uani . . . . . . . C204 C 0.4872(3) 0.8483(2) 0.38118(16) 0.0668 1.0000 Uani . . . . . . . C205 C 0.5464(2) 0.80481(19) 0.41062(17) 0.0650 1.0000 Uani . . . . . . . N206 N 0.5897(3) 0.7689(2) 0.4341(2) 0.1040 1.0000 Uani . . . . . . . C207 C 0.9684(16) 0.9634(13) 0.5099(10) 0.1425 0.5000 Uani . . . . -1 . . C208 C 1.0292(7) 1.0381(7) 0.4807(7) 0.0552 0.5000 Uani . . . . -1 . . N209 N 1.0753(6) 1.0939(5) 0.4543(4) 0.0976 0.5000 Uani . . . . -1 . . C210 C 0.6613(3) 0.1087(2) 0.02295(19) 0.0802 1.0000 Uani . . . . . . . C211 C 0.7396(2) 0.20419(19) 0.04631(16) 0.0591 1.0000 Uani . . . . . . . N212 N 0.8009(3) 0.2788(2) 0.0642(2) 0.1009 1.0000 Uani . . . . . . . H11 H 1.0874 0.6407 0.4191 0.0319 1.0000 Uiso R . . . . . . H31 H 0.9831 0.6630 0.6075 0.0331 1.0000 Uiso R . . . . . . H51 H 1.2490 0.6154 0.5815 0.0327 1.0000 Uiso R . . . . . . H81 H 1.1525 0.5464 0.7362 0.0675 0.723(4) Uiso R . P 1 1 . . H82 H 1.1878 0.5293 0.6614 0.0675 0.723(4) Uiso R . P 1 1 . . H83 H 1.0633 0.4951 0.6686 0.0670 0.723(4) Uiso R . P 1 1 . . H91 H 1.0602 0.6491 0.7713 0.0711 0.723(4) Uiso R . P 1 1 . . H92 H 1.0500 0.7128 0.7249 0.0715 0.723(4) Uiso R . P 1 1 . . H93 H 0.9778 0.6057 0.7027 0.0712 0.723(4) Uiso R . P 1 1 . . H101 H 1.2598 0.7131 0.7657 0.0671 0.723(4) Uiso R . P 1 1 . . H102 H 1.3046 0.7049 0.6935 0.0676 0.723(4) Uiso R . P 1 1 . . H103 H 1.2530 0.7754 0.7168 0.0679 0.723(4) Uiso R . P 1 1 . . H141 H 1.4197 0.5114 0.4370 0.0355 1.0000 Uiso R . . . . . . H142 H 1.4271 0.5904 0.4006 0.0351 1.0000 Uiso R . . . . . . H151 H 1.3658 0.4469 0.3152 0.0346 1.0000 Uiso R . . . . . . H152 H 1.2714 0.4817 0.3189 0.0348 1.0000 Uiso R . . . . . . H181 H 1.1345 0.2178 0.3762 0.0395 1.0000 Uiso R . . . . . . H191 H 1.0280 0.0839 0.2905 0.0418 1.0000 Uiso R . . . . . . H211 H 1.1151 0.2226 0.1413 0.0403 1.0000 Uiso R . . . . . . H221 H 1.2250 0.3552 0.2260 0.0387 1.0000 Uiso R . . . . . . H241 H 1.0163 0.0704 0.0657 0.0516 1.0000 Uiso R . . . . . . H242 H 0.9343 0.1150 0.0982 0.0512 1.0000 Uiso R . . . . . . H252 H 0.8740 -0.0793 0.0606 0.0530 1.0000 Uiso R . . . . . . H251 H 0.8339 -0.0257 0.0153 0.0538 1.0000 Uiso R . . . . . . H271 H 0.6824 -0.1594 0.0602 0.0678 1.0000 Uiso R . . . . . . H272 H 0.6493 -0.0901 0.0281 0.0684 1.0000 Uiso R . . . . . . H281 H 0.6157 -0.1131 0.1653 0.0730 1.0000 Uiso R . . . . . . H282 H 0.5221 -0.1659 0.0986 0.0718 1.0000 Uiso R . . . . . . H301 H 0.5087 -0.0427 0.2170 0.0815 1.0000 Uiso R . . . . . . H302 H 0.4160 -0.0811 0.1514 0.0810 1.0000 Uiso R . . . . . . H311 H 0.5562 0.1135 0.2048 0.0733 1.0000 Uiso R . . . . . . H312 H 0.4361 0.0661 0.2243 0.0742 1.0000 Uiso R . . . . . . H332 H 0.5231 0.2100 0.1583 0.0540 1.0000 Uiso R . . . . . . H331 H 0.4529 0.1724 0.0804 0.0546 1.0000 Uiso R . . . . . . H341 H 0.3602 0.2395 0.1457 0.0476 1.0000 Uiso R . . . . . . H342 H 0.2925 0.1297 0.1349 0.0494 1.0000 Uiso R . . . . . . H371 H 0.3741 0.2302 0.3589 0.0385 1.0000 Uiso R . . . . . . H381 H 0.4909 0.3625 0.4433 0.0378 1.0000 Uiso R . . . . . . H401 H 0.6177 0.4843 0.2905 0.0378 1.0000 Uiso R . . . . . . H411 H 0.5077 0.3489 0.2068 0.0401 1.0000 Uiso R . . . . . . H432 H 0.7355 0.5918 0.3763 0.0353 1.0000 Uiso R . . . . . . H431 H 0.6365 0.6173 0.3911 0.0353 1.0000 Uiso R . . . . . . H442 H 0.7803 0.7317 0.4679 0.0353 1.0000 Uiso R . . . . . . H441 H 0.7038 0.6687 0.5119 0.0361 1.0000 Uiso R . . . . . . H482 H 1.0390 0.5884 0.7545 0.0929 0.277(4) Uiso R . P 1 2 . . H483 H 1.0200 0.5148 0.6833 0.0929 0.277(4) Uiso R . P 1 2 . . H481 H 0.9728 0.5899 0.6890 0.0928 0.277(4) Uiso R . P 1 2 . . H502 H 1.2388 0.6472 0.7602 0.0718 0.277(4) Uiso R . P 1 2 . . H503 H 1.2956 0.6832 0.6979 0.0719 0.277(4) Uiso R . P 1 2 . . H501 H 1.2306 0.5762 0.6901 0.0719 0.277(4) Uiso R . P 1 2 . . H1011 H 1.4555 0.3614 0.0843 0.0318 1.0000 Uiso R . . . . . . H1031 H 1.3393 0.3363 -0.1132 0.0311 1.0000 Uiso R . . . . . . H1051 H 1.6614 0.4230 -0.0588 0.0340 1.0000 Uiso R . . . . . . H1082 H 1.6279 0.4789 -0.2198 0.0596 1.0000 Uiso R . . . . . . H1081 H 1.6759 0.4988 -0.1405 0.0597 1.0000 Uiso R . . . . . . H1083 H 1.5781 0.5250 -0.1607 0.0600 1.0000 Uiso R . . . . . . H1092 H 1.4427 0.3625 -0.2684 0.0753 1.0000 Uiso R . . . . . . H1093 H 1.3938 0.4029 -0.2055 0.0745 1.0000 Uiso R . . . . . . H1091 H 1.3678 0.2962 -0.2240 0.0747 1.0000 Uiso R . . . . . . H1102 H 1.5949 0.3180 -0.2475 0.0616 1.0000 Uiso R . . . . . . H1103 H 1.6377 0.3234 -0.1697 0.0622 1.0000 Uiso R . . . . . . H1101 H 1.5205 0.2493 -0.2053 0.0625 1.0000 Uiso R . . . . . . H1141 H 1.9204 0.5399 0.1064 0.0457 1.0000 Uiso R . . . . . . H1142 H 1.8542 0.4610 0.1412 0.0448 1.0000 Uiso R . . . . . . H1151 H 1.9170 0.6026 0.2248 0.0454 1.0000 Uiso R . . . . . . H1152 H 1.7868 0.5627 0.2085 0.0452 1.0000 Uiso R . . . . . . H1181 H 1.8623 0.8108 0.1428 0.0539 1.0000 Uiso R . . . . . . H1191 H 1.8406 0.9356 0.2165 0.0617 1.0000 Uiso R . . . . . . H1211 H 1.8476 0.8221 0.3780 0.0645 1.0000 Uiso R . . . . . . H1221 H 1.8697 0.6995 0.3036 0.0544 1.0000 Uiso R . . . . . . H1242 H 1.8373 1.0512 0.2973 0.0847 1.0000 Uiso R . . . . . . H1241 H 1.7155 0.9792 0.3014 0.0841 1.0000 Uiso R . . . . . . H1251 H 1.8509 1.1150 0.4250 0.0984 1.0000 Uiso R . . . . . . H1252 H 1.7684 1.1362 0.3743 0.1009 1.0000 Uiso R . . . . . . H1271 H 1.7411 1.1704 0.4929 0.0854 1.0000 Uiso R . . . . . . H1272 H 1.6393 1.0790 0.5105 0.0866 1.0000 Uiso R . . . . . . H1281 H 1.5912 1.1978 0.4746 0.0707 1.0000 Uiso R . . . . . . H1282 H 1.6030 1.1528 0.3963 0.0691 1.0000 Uiso R . . . . . . H1302 H 1.4159 1.1514 0.4266 0.0657 1.0000 Uiso R . . . . . . H1301 H 1.4157 1.0835 0.3534 0.0660 1.0000 Uiso R . . . . . . H1312 H 1.2856 1.0144 0.4540 0.0611 1.0000 Uiso R . . . . . . H1311 H 1.2386 1.0393 0.3878 0.0624 1.0000 Uiso R . . . . . . H1332 H 1.1514 0.8607 0.4102 0.0533 1.0000 Uiso R . . . . . . H1331 H 1.1135 0.8806 0.3389 0.0537 1.0000 Uiso R . . . . . . H1342 H 1.2090 0.7545 0.3375 0.0463 1.0000 Uiso R . . . . . . H1341 H 1.0806 0.7217 0.3244 0.0468 1.0000 Uiso R . . . . . . H1371 H 1.1624 0.7495 0.1207 0.0420 1.0000 Uiso R . . . . . . H1381 H 1.1429 0.6182 0.0356 0.0404 1.0000 Uiso R . . . . . . H1401 H 1.1101 0.4753 0.1825 0.0397 1.0000 Uiso R . . . . . . H1411 H 1.1319 0.6063 0.2676 0.0411 1.0000 Uiso R . . . . . . H1432 H 1.1355 0.3740 0.1000 0.0385 1.0000 Uiso R . . . . . . H1431 H 1.0134 0.3513 0.0747 0.0386 1.0000 Uiso R . . . . . . H1441 H 1.0578 0.2416 0.0039 0.0399 1.0000 Uiso R . . . . . . H1442 H 1.0404 0.3049 -0.0412 0.0397 1.0000 Uiso R . . . . . . H2011 H 0.2010 -0.0690 0.2250 0.0831 1.0000 Uiso R . . . . . . H2013 H 0.0947 -0.0497 0.2289 0.0834 1.0000 Uiso R . . . . . . H2012 H 0.2066 0.0306 0.2234 0.0834 1.0000 Uiso R . . . . . . H2043 H 0.5093 0.8590 0.3367 0.1013 1.0000 Uiso R . . . . . . H2041 H 0.5009 0.9077 0.4134 0.1006 1.0000 Uiso R . . . . . . H2042 H 0.4100 0.8078 0.3745 0.1010 1.0000 Uiso R . . . . . . H2101 H 0.6520 0.0803 0.0620 0.1217 1.0000 Uiso R . . . . . . H2103 H 0.6848 0.0761 -0.0149 0.1215 1.0000 Uiso R . . . . . . H2102 H 0.5939 0.1105 0.0071 0.1218 1.0000 Uiso R . . . . . . H131 H 1.2981 0.5374 0.4948 0.0338 1.0000 Uiso R . . . . . . H1451 H 1.2075 0.3492 -0.0595 0.0345 1.0000 Uiso R . . . . . . H451 H 0.8343 0.6299 0.5401 0.0350 1.0000 Uiso R . . . . . . H1131 H 1.7755 0.4922 0.0324 0.0407 1.0000 Uiso R . . . . . . H2071 H 0.9794 0.9865 0.5597 0.2002 0.5000 Uiso R . . . -1 . . H2072 H 0.9939 0.9152 0.4970 0.2002 0.5000 Uiso R . . . -1 . . H2073 H 0.8922 0.9398 0.4927 0.2002 0.5000 Uiso R . . . -1 . . H491 H 1.2164 0.7956 0.7207 0.0970 0.277(4) Uiso R . P 1 2 . . H492 H 1.1509 0.7538 0.7774 0.0971 0.277(4) Uiso R . P 1 2 . . H493 H 1.0902 0.7618 0.7123 0.0968 0.277(4) Uiso R . P 1 2 . . 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 0.0256(8) 0.0319(9) 0.0259(8) 0.0129(7) 0.0039(7) 0.0120(7) C2 0.0235(8) 0.0305(9) 0.0288(9) 0.0128(7) 0.0039(7) 0.0125(7) C3 0.0249(8) 0.0354(9) 0.0271(9) 0.0135(7) 0.0065(7) 0.0143(7) C4 0.0259(8) 0.0334(9) 0.0260(8) 0.0123(7) 0.0042(7) 0.0129(7) C5 0.0239(8) 0.0327(9) 0.0308(9) 0.0126(7) 0.0036(7) 0.0151(7) C6 0.0238(8) 0.0266(8) 0.0298(9) 0.0115(7) 0.0051(7) 0.0114(7) C7 0.0343(10) 0.0522(11) 0.0258(9) 0.0168(8) 0.0047(7) 0.0203(9) C8 0.0573(19) 0.0537(16) 0.0369(16) 0.0260(14) 0.0091(13) 0.0276(15) C9 0.0502(18) 0.081(3) 0.0295(15) 0.0226(17) 0.0123(12) 0.0402(19) C10 0.0450(15) 0.0530(19) 0.0322(15) 0.0117(13) -0.0037(12) 0.0154(13) C11 0.0264(9) 0.0313(9) 0.0281(9) 0.0118(7) 0.0048(7) 0.0139(7) O12 0.0461(8) 0.0551(9) 0.0365(7) 0.0269(7) 0.0182(6) 0.0336(7) N13 0.0300(8) 0.0367(8) 0.0271(7) 0.0146(6) 0.0091(6) 0.0195(7) C14 0.0275(9) 0.0365(10) 0.0341(10) 0.0136(8) 0.0088(7) 0.0175(8) C15 0.0305(9) 0.0350(10) 0.0297(9) 0.0145(8) 0.0115(7) 0.0159(8) O16 0.0374(7) 0.0349(7) 0.0273(6) 0.0130(5) 0.0098(5) 0.0133(6) C17 0.0302(9) 0.0351(10) 0.0291(9) 0.0120(8) 0.0092(7) 0.0168(8) C18 0.0396(10) 0.0395(10) 0.0277(9) 0.0149(8) 0.0106(8) 0.0201(9) C19 0.0418(11) 0.0339(10) 0.0348(10) 0.0164(8) 0.0121(8) 0.0165(9) C20 0.0345(10) 0.0348(10) 0.0316(10) 0.0099(8) 0.0071(8) 0.0163(8) C21 0.0362(10) 0.0415(11) 0.0279(9) 0.0149(8) 0.0108(8) 0.0187(9) C22 0.0329(10) 0.0369(10) 0.0317(9) 0.0157(8) 0.0120(8) 0.0153(8) O23 0.0504(9) 0.0363(8) 0.0325(7) 0.0120(6) 0.0022(6) 0.0132(7) C24 0.0511(13) 0.0481(12) 0.0297(10) 0.0145(9) 0.0073(9) 0.0181(10) C25 0.0566(14) 0.0436(12) 0.0324(10) 0.0072(9) 0.0045(9) 0.0199(11) O26 0.0475(9) 0.0388(8) 0.0410(8) 0.0069(6) 0.0035(7) 0.0128(7) C27 0.0533(14) 0.0323(11) 0.0731(17) -0.0006(11) -0.0034(12) 0.0151(10) C28 0.0492(14) 0.0360(12) 0.093(2) 0.0209(13) 0.0072(13) 0.0150(11) O29 0.0548(10) 0.0465(9) 0.0812(13) 0.0272(9) 0.0210(9) 0.0257(8) C30 0.0671(18) 0.0724(19) 0.085(2) 0.0402(16) 0.0285(15) 0.0393(15) C31 0.0744(18) 0.0739(18) 0.0544(15) 0.0186(13) 0.0114(13) 0.0458(16) O32 0.0618(11) 0.0467(9) 0.0499(9) 0.0024(7) -0.0038(8) 0.0256(8) C33 0.0590(14) 0.0447(12) 0.0320(10) 0.0073(9) 0.0050(10) 0.0210(11) C34 0.0447(12) 0.0406(11) 0.0335(10) 0.0116(9) -0.0029(9) 0.0137(9) O35 0.0408(8) 0.0346(7) 0.0359(7) 0.0109(6) 0.0049(6) 0.0141(6) C36 0.0311(9) 0.0340(10) 0.0349(10) 0.0119(8) 0.0053(8) 0.0178(8) C37 0.0314(9) 0.0369(10) 0.0372(10) 0.0195(8) 0.0089(8) 0.0165(8) C38 0.0329(10) 0.0409(10) 0.0303(9) 0.0175(8) 0.0088(8) 0.0198(8) C39 0.0271(9) 0.0363(10) 0.0296(9) 0.0129(8) 0.0039(7) 0.0176(8) C40 0.0312(9) 0.0367(10) 0.0332(10) 0.0173(8) 0.0074(8) 0.0156(8) C41 0.0370(10) 0.0404(10) 0.0290(9) 0.0146(8) 0.0074(8) 0.0199(9) O42 0.0325(7) 0.0373(7) 0.0285(6) 0.0144(6) 0.0029(5) 0.0127(6) C43 0.0255(9) 0.0373(10) 0.0331(9) 0.0168(8) 0.0047(7) 0.0152(8) C44 0.0245(9) 0.0395(10) 0.0347(10) 0.0133(8) 0.0050(7) 0.0174(8) N45 0.0240(7) 0.0404(9) 0.0277(7) 0.0159(7) 0.0055(6) 0.0163(7) C46 0.0267(9) 0.0403(10) 0.0297(9) 0.0169(8) 0.0060(7) 0.0171(8) O47 0.0353(8) 0.0812(11) 0.0474(9) 0.0448(8) 0.0158(6) 0.0329(8) C48 0.041(3) 0.105(7) 0.040(5) 0.043(5) 0.014(3) 0.022(4) C49 0.088(7) 0.080(4) 0.029(4) -0.001(3) -0.005(4) 0.057(5) C50 0.044(3) 0.083(7) 0.031(4) 0.024(4) 0.010(3) 0.039(4) C101 0.0251(8) 0.0305(9) 0.0257(8) 0.0128(7) 0.0067(7) 0.0110(7) C102 0.0232(8) 0.0261(8) 0.0272(8) 0.0116(7) 0.0061(7) 0.0099(7) C103 0.0239(8) 0.0307(9) 0.0280(9) 0.0114(7) 0.0035(7) 0.0108(7) C104 0.0267(9) 0.0294(9) 0.0252(8) 0.0115(7) 0.0058(7) 0.0111(7) C105 0.0219(8) 0.0342(9) 0.0293(9) 0.0129(7) 0.0073(7) 0.0104(7) C106 0.0234(8) 0.0324(9) 0.0276(9) 0.0126(7) 0.0042(7) 0.0115(7) C107 0.0289(9) 0.0414(10) 0.0237(9) 0.0133(8) 0.0064(7) 0.0123(8) C108 0.0467(12) 0.0434(11) 0.0333(10) 0.0187(9) 0.0147(9) 0.0162(10) C109 0.0369(11) 0.0874(18) 0.0282(10) 0.0249(11) 0.0048(9) 0.0206(12) C110 0.0486(12) 0.0437(12) 0.0324(10) 0.0097(9) 0.0148(9) 0.0177(10) C111 0.0251(9) 0.0450(11) 0.0299(9) 0.0174(8) 0.0057(7) 0.0139(8) O112 0.0289(7) 0.0759(11) 0.0354(8) 0.0331(8) 0.0040(6) 0.0109(7) N113 0.0226(7) 0.0475(9) 0.0296(8) 0.0194(7) 0.0038(6) 0.0106(7) C114 0.0205(9) 0.0543(12) 0.0415(11) 0.0242(10) 0.0007(8) 0.0116(8) C115 0.0274(9) 0.0507(12) 0.0353(10) 0.0212(9) -0.0024(8) 0.0104(9) O116 0.0384(8) 0.0503(9) 0.0356(7) 0.0238(7) 0.0016(6) 0.0116(7) C117 0.0309(10) 0.0413(11) 0.0333(10) 0.0142(9) -0.0050(8) 0.0026(8) C118 0.0416(12) 0.0459(12) 0.0366(11) 0.0225(10) -0.0035(9) 0.0028(9) C119 0.0560(14) 0.0395(12) 0.0442(12) 0.0176(10) -0.0091(10) 0.0039(10) C120 0.0645(16) 0.0438(13) 0.0415(12) 0.0118(10) -0.0102(11) 0.0094(11) C121 0.0713(17) 0.0509(14) 0.0295(11) 0.0121(10) -0.0086(10) 0.0153(12) C122 0.0436(12) 0.0506(13) 0.0367(11) 0.0223(10) -0.0066(9) 0.0088(10) O123 0.131(2) 0.0537(11) 0.0488(11) 0.0018(9) -0.0169(11) 0.0395(12) C124 0.0576(16) 0.091(2) 0.0711(19) 0.0287(17) 0.0232(14) 0.0376(16) C125 0.0629(19) 0.086(2) 0.089(2) 0.0145(18) 0.0275(17) 0.0278(17) O126 0.0622(12) 0.0444(10) 0.1147(18) 0.0025(11) 0.0304(12) 0.0150(9) C127 0.0619(17) 0.0446(14) 0.092(2) -0.0088(14) 0.0046(15) 0.0218(13) C128 0.0670(17) 0.0335(12) 0.0668(17) 0.0060(11) 0.0162(13) 0.0135(11) O129 0.0577(10) 0.0362(8) 0.0540(10) 0.0128(7) 0.0068(8) 0.0173(7) C130 0.0792(18) 0.0411(12) 0.0449(13) 0.0137(10) 0.0003(12) 0.0262(12) C131 0.0644(15) 0.0468(13) 0.0481(13) 0.0082(10) 0.0024(11) 0.0317(12) O132 0.0493(9) 0.0418(8) 0.0487(9) 0.0080(7) 0.0068(7) 0.0200(7) C133 0.0444(12) 0.0532(13) 0.0403(12) 0.0145(10) 0.0083(9) 0.0225(10) C134 0.0397(11) 0.0469(12) 0.0345(10) 0.0173(9) 0.0077(8) 0.0194(9) O135 0.0528(9) 0.0418(8) 0.0360(8) 0.0167(6) 0.0109(6) 0.0243(7) C136 0.0295(9) 0.0417(11) 0.0389(10) 0.0172(9) 0.0105(8) 0.0190(8) C137 0.0314(10) 0.0404(11) 0.0422(11) 0.0225(9) 0.0099(8) 0.0176(8) C138 0.0286(9) 0.0458(11) 0.0362(10) 0.0213(9) 0.0104(8) 0.0183(8) C139 0.0231(9) 0.0400(10) 0.0377(10) 0.0167(8) 0.0089(7) 0.0163(8) C140 0.0296(9) 0.0434(11) 0.0412(11) 0.0237(9) 0.0141(8) 0.0205(8) C141 0.0334(10) 0.0465(11) 0.0346(10) 0.0214(9) 0.0123(8) 0.0208(9) O142 0.0361(7) 0.0400(7) 0.0364(7) 0.0180(6) 0.0126(6) 0.0194(6) C143 0.0241(9) 0.0389(10) 0.0413(10) 0.0213(9) 0.0121(8) 0.0133(8) C144 0.0192(8) 0.0412(11) 0.0402(10) 0.0154(9) 0.0043(7) 0.0105(8) N145 0.0223(7) 0.0414(9) 0.0290(8) 0.0173(7) 0.0063(6) 0.0131(7) C146 0.0237(8) 0.0296(9) 0.0280(9) 0.0113(7) 0.0045(7) 0.0102(7) O147 0.0295(7) 0.0573(9) 0.0397(8) 0.0318(7) 0.0132(6) 0.0196(6) C201 0.0659(16) 0.0478(13) 0.0589(15) 0.0208(12) 0.0095(12) 0.0267(12) C202 0.0570(15) 0.0363(12) 0.0630(17) 0.0169(11) 0.0105(12) 0.0145(11) N203 0.093(2) 0.0559(14) 0.0627(16) 0.0124(12) 0.0083(14) 0.0092(13) C204 0.081(2) 0.0480(15) 0.0596(16) 0.0068(12) 0.0072(14) 0.0188(14) C205 0.0637(17) 0.0458(14) 0.0776(19) -0.0024(13) 0.0195(14) 0.0235(13) N206 0.099(2) 0.084(2) 0.142(3) 0.009(2) 0.012(2) 0.062(2) C207 0.159(16) 0.132(15) 0.071(8) 0.032(8) -0.010(8) -0.008(11) C208 0.046(4) 0.044(5) 0.070(6) 0.017(4) 0.007(4) 0.011(4) N209 0.095(5) 0.085(4) 0.101(5) 0.044(4) 0.003(4) 0.016(4) C210 0.082(2) 0.0534(17) 0.088(2) 0.0133(16) 0.0312(18) 0.0115(15) C211 0.0564(15) 0.0507(15) 0.0733(18) 0.0251(13) 0.0183(13) 0.0197(13) N212 0.0714(19) 0.0655(18) 0.143(3) 0.0167(18) 0.0234(19) 0.0098(15) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.8629(18) 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 . C2 . 1.383(2) yes C1 . C6 . 1.393(2) yes C1 . H11 . 0.942 no C2 . C3 . 1.397(2) yes C2 . C46 . 1.505(2) yes C3 . C4 . 1.397(2) yes C3 . H31 . 0.938 no C4 . C5 . 1.397(2) yes C4 . C7 . 1.532(2) yes C5 . C6 . 1.392(2) yes C5 . H51 . 0.931 no C6 . C11 . 1.498(2) yes C7 . C8 . 1.587(4) yes C7 . C9 . 1.490(4) yes C7 . C10 . 1.519(4) yes C7 . C48 . 1.497(9) yes C7 . C49 . 1.725(10) yes C7 . C50 . 1.426(8) yes C8 . H81 . 0.970 no C8 . H82 . 0.970 no C8 . H83 . 0.978 no C9 . H91 . 0.964 no C9 . H92 . 0.967 no C9 . H93 . 0.968 no C10 . H101 . 0.968 no C10 . H102 . 0.970 no C10 . H103 . 0.962 no C11 . O12 . 1.231(2) yes C11 . N13 . 1.349(2) yes N13 . C14 . 1.457(2) yes N13 . H131 . 0.859 no C14 . C15 . 1.509(3) yes C14 . H141 . 0.971 no C14 . H142 . 0.980 no C15 . O16 . 1.434(2) yes C15 . H151 . 0.983 no C15 . H152 . 0.982 no O16 . C17 . 1.382(2) yes C17 . C18 . 1.394(3) yes C17 . C22 . 1.385(3) yes C18 . C19 . 1.374(3) yes C18 . H181 . 0.958 no C19 . C20 . 1.395(3) yes C19 . H191 . 0.930 no C20 . C21 . 1.384(3) yes C20 . O23 . 1.373(2) yes C21 . C22 . 1.392(3) yes C21 . H211 . 0.951 no C22 . H221 . 0.938 no O23 . C24 . 1.432(2) yes C24 . C25 . 1.496(3) yes C24 . H241 . 1.006 no C24 . H242 . 0.982 no C25 . O26 . 1.423(3) yes C25 . H252 . 0.980 no C25 . H251 . 0.983 no O26 . C27 . 1.401(3) yes C27 . C28 . 1.485(4) yes C27 . H271 . 0.979 no C27 . H272 . 0.986 no C28 . O29 . 1.413(3) yes C28 . H281 . 0.998 no C28 . H282 . 0.998 no O29 . C30 . 1.412(3) yes C30 . C31 . 1.507(4) yes C30 . H301 . 0.968 no C30 . H302 . 1.010 no C31 . O32 . 1.414(3) yes C31 . H311 . 0.987 no C31 . H312 . 0.974 no O32 . C33 . 1.425(3) yes C33 . C34 . 1.503(3) yes C33 . H332 . 0.997 no C33 . H331 . 1.005 no C34 . O35 . 1.440(2) yes C34 . H341 . 0.978 no C34 . H342 . 0.979 no O35 . C36 . 1.375(2) yes C36 . C37 . 1.395(3) yes C36 . C41 . 1.385(3) yes C37 . C38 . 1.375(3) yes C37 . H371 . 0.942 no C38 . C39 . 1.397(3) yes C38 . H381 . 0.951 no C39 . C40 . 1.384(3) yes C39 . O42 . 1.381(2) yes C40 . C41 . 1.395(3) yes C40 . H401 . 0.948 no C41 . H411 . 0.946 no O42 . C43 . 1.440(2) yes C43 . C44 . 1.505(3) yes C43 . H432 . 0.970 no C43 . H431 . 0.965 no C44 . N45 . 1.464(2) yes C44 . H442 . 0.977 no C44 . H441 . 0.966 no N45 . C46 . 1.342(2) yes N45 . H451 . 0.853 no C46 . O47 . 1.229(2) yes C48 . H482 . 0.963 no C48 . H483 . 0.966 no C48 . H481 . 0.962 no C49 . H491 . 0.959 no C49 . H492 . 0.958 no C49 . H493 . 0.959 no C50 . H502 . 0.967 no C50 . H503 . 0.967 no C50 . H501 . 0.962 no C101 . C102 . 1.384(2) yes C101 . C106 . 1.391(2) yes C101 . H1011 . 0.957 no C102 . C103 . 1.400(2) yes C102 . C146 . 1.504(2) yes C103 . C104 . 1.398(2) yes C103 . H1031 . 0.941 no C104 . C105 . 1.396(2) yes C104 . C107 . 1.538(2) yes C105 . C106 . 1.390(2) yes C105 . H1051 . 0.954 no C106 . C111 . 1.508(2) yes C107 . C108 . 1.532(3) yes C107 . C109 . 1.525(3) yes C107 . C110 . 1.538(3) yes C108 . H1082 . 0.963 no C108 . H1081 . 0.992 no C108 . H1083 . 0.975 no C109 . H1092 . 0.977 no C109 . H1093 . 0.956 no C109 . H1091 . 0.991 no C110 . H1102 . 0.986 no C110 . H1103 . 0.977 no C110 . H1101 . 0.975 no C111 . O112 . 1.227(2) yes C111 . N113 . 1.342(2) yes N113 . C114 . 1.462(2) yes N113 . H1131 . 0.849 no C114 . C115 . 1.504(3) yes C114 . H1141 . 0.958 no C114 . H1142 . 0.969 no C115 . O116 . 1.434(2) yes C115 . H1151 . 0.982 no C115 . H1152 . 0.991 no O116 . C117 . 1.385(3) yes C117 . C118 . 1.393(3) yes C117 . C122 . 1.389(3) yes C118 . C119 . 1.386(4) yes C118 . H1181 . 0.948 no C119 . C120 . 1.392(3) yes C119 . H1191 . 0.957 no C120 . C121 . 1.388(3) yes C120 . O123 . 1.375(3) yes C121 . C122 . 1.387(4) yes C121 . H1211 . 0.948 no C122 . H1221 . 0.936 no O123 . C124 . 1.399(4) yes C124 . C125 . 1.508(5) yes C124 . H1242 . 1.010 no C124 . H1241 . 0.985 no C125 . O126 . 1.357(4) yes C125 . H1251 . 1.011 no C125 . H1252 . 0.995 no O126 . C127 . 1.423(3) yes C127 . C128 . 1.511(4) yes C127 . H1271 . 1.018 no C127 . H1272 . 1.040 no C128 . O129 . 1.424(3) yes C128 . H1281 . 1.002 no C128 . H1282 . 0.973 no O129 . C130 . 1.410(3) yes C130 . C131 . 1.497(4) yes C130 . H1302 . 1.005 no C130 . H1301 . 0.971 no C131 . O132 . 1.423(3) yes C131 . H1312 . 0.985 no C131 . H1311 . 1.007 no O132 . C133 . 1.423(3) yes C133 . C134 . 1.493(3) yes C133 . H1332 . 0.993 no C133 . H1331 . 0.988 no C134 . O135 . 1.432(2) yes C134 . H1342 . 0.965 no C134 . H1341 . 0.988 no O135 . C136 . 1.370(3) yes C136 . C137 . 1.400(3) yes C136 . C141 . 1.387(3) yes C137 . C138 . 1.374(3) yes C137 . H1371 . 0.952 no C138 . C139 . 1.399(3) yes C138 . H1381 . 0.947 no C139 . C140 . 1.385(3) yes C139 . O142 . 1.384(2) yes C140 . C141 . 1.390(3) yes C140 . H1401 . 0.942 no C141 . H1411 . 0.936 no O142 . C143 . 1.441(2) yes C143 . C144 . 1.506(3) yes C143 . H1432 . 0.979 no C143 . H1431 . 0.960 no C144 . N145 . 1.463(2) yes C144 . H1441 . 0.960 no C144 . H1442 . 0.965 no N145 . C146 . 1.344(2) yes N145 . H1451 . 0.858 no C146 . O147 . 1.228(2) yes C201 . C202 . 1.450(4) yes C201 . H2011 . 0.973 no C201 . H2013 . 0.979 no C201 . H2012 . 0.972 no C202 . N203 . 1.136(4) yes C204 . C205 . 1.443(5) yes C204 . H2043 . 0.973 no C204 . H2041 . 0.976 no C204 . H2042 . 0.974 no C205 . N206 . 1.129(4) yes C207 . C208 . 1.425(12) yes C207 . H2071 . 0.961 no C207 . H2072 . 0.965 no C207 . H2073 . 0.966 no C208 . N209 . 1.125(13) yes C210 . C211 . 1.442(4) yes C210 . H2101 . 0.974 no C210 . H2103 . 0.961 no C210 . H2102 . 0.970 no C211 . N212 . 1.128(4) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 120.12(16) yes C2 . C1 . H11 . 121.0 no C6 . C1 . H11 . 118.9 no C1 . C2 . C3 . 119.94(16) yes C1 . C2 . C46 . 116.39(15) yes C3 . C2 . C46 . 123.64(16) yes C2 . C3 . C4 . 121.19(16) yes C2 . C3 . H31 . 119.7 no C4 . C3 . H31 . 119.1 no C3 . C4 . C5 . 117.56(16) yes C3 . C4 . C7 . 122.19(16) yes C5 . C4 . C7 . 120.25(16) yes C4 . C5 . C6 . 121.91(16) yes C4 . C5 . H51 . 118.3 no C6 . C5 . H51 . 119.8 no C1 . C6 . C5 . 119.24(16) yes C1 . C6 . C11 . 116.53(15) yes C5 . C6 . C11 . 124.23(15) yes C4 . C7 . C8 . 107.42(18) yes C4 . C7 . C9 . 113.82(18) yes C8 . C7 . C9 . 107.3(2) yes C4 . C7 . C10 . 109.54(18) yes C8 . C7 . C10 . 106.5(2) yes C9 . C7 . C10 . 111.9(2) yes C4 . C7 . C48 . 110.1(4) yes C4 . C7 . C49 . 104.3(3) yes C48 . C7 . C49 . 102.6(7) yes C4 . C7 . C50 . 117.8(3) yes C48 . C7 . C50 . 116.1(6) yes C49 . C7 . C50 . 103.8(5) yes C7 . C8 . H81 . 108.1 no C7 . C8 . H82 . 113.0 no H81 . C8 . H82 . 109.0 no C7 . C8 . H83 . 108.7 no H81 . C8 . H83 . 110.1 no H82 . C8 . H83 . 108.0 no C7 . C9 . H91 . 111.2 no C7 . C9 . H92 . 109.2 no H91 . C9 . H92 . 108.4 no C7 . C9 . H93 . 111.9 no H91 . C9 . H93 . 108.0 no H92 . C9 . H93 . 108.0 no C7 . C10 . H101 . 109.1 no C7 . C10 . H102 . 111.6 no H101 . C10 . H102 . 109.0 no C7 . C10 . H103 . 110.0 no H101 . C10 . H103 . 109.0 no H102 . C10 . H103 . 108.0 no C6 . C11 . O12 . 121.41(16) yes C6 . C11 . N13 . 116.56(15) yes O12 . C11 . N13 . 122.02(16) yes C11 . N13 . C14 . 121.48(15) yes C11 . N13 . H131 . 120.2 no C14 . N13 . H131 . 118.3 no N13 . C14 . C15 . 112.72(15) yes N13 . C14 . H141 . 107.0 no C15 . C14 . H141 . 110.5 no N13 . C14 . H142 . 107.8 no C15 . C14 . H142 . 110.8 no H141 . C14 . H142 . 107.8 no C14 . C15 . O16 . 108.23(14) yes C14 . C15 . H151 . 110.0 no O16 . C15 . H151 . 109.3 no C14 . C15 . H152 . 110.8 no O16 . C15 . H152 . 110.4 no H151 . C15 . H152 . 108.1 no C15 . O16 . C17 . 116.49(14) yes O16 . C17 . C18 . 115.76(16) yes O16 . C17 . C22 . 124.63(17) yes C18 . C17 . C22 . 119.62(18) yes C17 . C18 . C19 . 120.16(17) yes C17 . C18 . H181 . 119.3 no C19 . C18 . H181 . 120.5 no C18 . C19 . C20 . 120.34(18) yes C18 . C19 . H191 . 120.0 no C20 . C19 . H191 . 119.7 no C19 . C20 . C21 . 119.61(18) yes C19 . C20 . O23 . 115.96(17) yes C21 . C20 . O23 . 124.41(17) yes C20 . C21 . C22 . 120.01(17) yes C20 . C21 . H211 . 120.7 no C22 . C21 . H211 . 119.3 no C21 . C22 . C17 . 120.16(17) yes C21 . C22 . H221 . 119.3 no C17 . C22 . H221 . 120.6 no C20 . O23 . C24 . 116.86(15) yes O23 . C24 . C25 . 107.40(17) yes O23 . C24 . H241 . 108.8 no C25 . C24 . H241 . 111.0 no O23 . C24 . H242 . 111.0 no C25 . C24 . H242 . 108.1 no H241 . C24 . H242 . 110.5 no C24 . C25 . O26 . 108.32(17) yes C24 . C25 . H252 . 110.8 no O26 . C25 . H252 . 111.3 no C24 . C25 . H251 . 109.7 no O26 . C25 . H251 . 107.8 no H252 . C25 . H251 . 108.9 no C25 . O26 . C27 . 112.44(18) yes O26 . C27 . C28 . 110.2(2) yes O26 . C27 . H271 . 108.7 no C28 . C27 . H271 . 110.0 no O26 . C27 . H272 . 108.8 no C28 . C27 . H272 . 109.9 no H271 . C27 . H272 . 109.2 no C27 . C28 . O29 . 109.5(2) yes C27 . C28 . H281 . 110.6 no O29 . C28 . H281 . 108.8 no C27 . C28 . H282 . 109.2 no O29 . C28 . H282 . 110.5 no H281 . C28 . H282 . 108.3 no C28 . O29 . C30 . 113.2(2) yes O29 . C30 . C31 . 108.5(2) yes O29 . C30 . H301 . 109.5 no C31 . C30 . H301 . 111.0 no O29 . C30 . H302 . 109.7 no C31 . C30 . H302 . 109.9 no H301 . C30 . H302 . 108.2 no C30 . C31 . O32 . 108.8(2) yes C30 . C31 . H311 . 110.2 no O32 . C31 . H311 . 108.0 no C30 . C31 . H312 . 109.5 no O32 . C31 . H312 . 110.6 no H311 . C31 . H312 . 109.7 no C31 . O32 . C33 . 114.10(19) yes O32 . C33 . C34 . 113.23(19) yes O32 . C33 . H332 . 108.4 no C34 . C33 . H332 . 111.0 no O32 . C33 . H331 . 107.2 no C34 . C33 . H331 . 107.0 no H332 . C33 . H331 . 110.0 no C33 . C34 . O35 . 113.28(17) yes C33 . C34 . H341 . 109.5 no O35 . C34 . H341 . 110.4 no C33 . C34 . H342 . 107.7 no O35 . C34 . H342 . 105.6 no H341 . C34 . H342 . 110.2 no C34 . O35 . C36 . 117.41(15) yes O35 . C36 . C37 . 115.18(17) yes O35 . C36 . C41 . 125.57(17) yes C37 . C36 . C41 . 119.24(18) yes C36 . C37 . C38 . 120.79(17) yes C36 . C37 . H371 . 118.4 no C38 . C37 . H371 . 120.8 no C37 . C38 . C39 . 120.12(17) yes C37 . C38 . H381 . 120.1 no C39 . C38 . H381 . 119.8 no C38 . C39 . C40 . 119.33(18) yes C38 . C39 . O42 . 115.78(16) yes C40 . C39 . O42 . 124.89(17) yes C39 . C40 . C41 . 120.45(17) yes C39 . C40 . H401 . 119.6 no C41 . C40 . H401 . 120.0 no C40 . C41 . C36 . 120.02(17) yes C40 . C41 . H411 . 119.1 no C36 . C41 . H411 . 120.9 no C39 . O42 . C43 . 117.24(14) yes O42 . C43 . C44 . 107.42(14) yes O42 . C43 . H432 . 109.8 no C44 . C43 . H432 . 111.6 no O42 . C43 . H431 . 109.5 no C44 . C43 . H431 . 109.5 no H432 . C43 . H431 . 109.0 no C43 . C44 . N45 . 112.08(15) yes C43 . C44 . H442 . 109.1 no N45 . C44 . H442 . 110.0 no C43 . C44 . H441 . 109.3 no N45 . C44 . H441 . 107.4 no H442 . C44 . H441 . 109.0 no C44 . N45 . C46 . 120.80(15) yes C44 . N45 . H451 . 119.9 no C46 . N45 . H451 . 119.3 no C2 . C46 . N45 . 117.41(15) yes C2 . C46 . O47 . 120.57(16) yes N45 . C46 . O47 . 122.01(16) yes C7 . C48 . H482 . 110.1 no C7 . C48 . H483 . 108.4 no H482 . C48 . H483 . 109.5 no C7 . C48 . H481 . 110.7 no H482 . C48 . H481 . 108.7 no H483 . C48 . H481 . 109.4 no C7 . C49 . H491 . 108.9 no C7 . C49 . H492 . 109.5 no H491 . C49 . H492 . 109.3 no C7 . C49 . H493 . 110.4 no H491 . C49 . H493 . 109.4 no H492 . C49 . H493 . 109.4 no C7 . C50 . H502 . 109.7 no C7 . C50 . H503 . 110.2 no H502 . C50 . H503 . 109.4 no C7 . C50 . H501 . 109.7 no H502 . C50 . H501 . 108.9 no H503 . C50 . H501 . 108.9 no C102 . C101 . C106 . 120.40(16) yes C102 . C101 . H1011 . 119.7 no C106 . C101 . H1011 . 119.9 no C101 . C102 . C103 . 119.87(15) yes C101 . C102 . C146 . 116.32(15) yes C103 . C102 . C146 . 123.80(15) yes C102 . C103 . C104 . 120.64(16) yes C102 . C103 . H1031 . 119.2 no C104 . C103 . H1031 . 120.1 no C103 . C104 . C105 . 118.12(16) yes C103 . C104 . C107 . 122.44(16) yes C105 . C104 . C107 . 119.43(15) yes C104 . C105 . C106 . 121.69(16) yes C104 . C105 . H1051 . 118.3 no C106 . C105 . H1051 . 120.0 no C101 . C106 . C105 . 119.15(16) yes C101 . C106 . C111 . 116.23(15) yes C105 . C106 . C111 . 124.60(16) yes C104 . C107 . C108 . 109.56(16) yes C104 . C107 . C109 . 112.27(15) yes C108 . C107 . C109 . 108.66(18) yes C104 . C107 . C110 . 109.06(15) yes C108 . C107 . C110 . 108.49(16) yes C109 . C107 . C110 . 108.73(18) yes C107 . C108 . H1082 . 108.4 no C107 . C108 . H1081 . 110.8 no H1082 . C108 . H1081 . 109.3 no C107 . C108 . H1083 . 110.2 no H1082 . C108 . H1083 . 108.5 no H1081 . C108 . H1083 . 109.7 no C107 . C109 . H1092 . 109.0 no C107 . C109 . H1093 . 109.7 no H1092 . C109 . H1093 . 109.1 no C107 . C109 . H1091 . 111.8 no H1092 . C109 . H1091 . 109.2 no H1093 . C109 . H1091 . 108.0 no C107 . C110 . H1102 . 109.6 no C107 . C110 . H1103 . 111.1 no H1102 . C110 . H1103 . 109.2 no C107 . C110 . H1101 . 110.3 no H1102 . C110 . H1101 . 108.5 no H1103 . C110 . H1101 . 108.0 no C106 . C111 . O112 . 120.86(16) yes C106 . C111 . N113 . 117.35(15) yes O112 . C111 . N113 . 121.73(17) yes C111 . N113 . C114 . 121.16(15) yes C111 . N113 . H1131 . 118.6 no C114 . N113 . H1131 . 119.0 no N113 . C114 . C115 . 113.27(17) yes N113 . C114 . H1141 . 107.5 no C115 . C114 . H1141 . 109.2 no N113 . C114 . H1142 . 108.6 no C115 . C114 . H1142 . 109.8 no H1141 . C114 . H1142 . 108.3 no C114 . C115 . O116 . 108.22(16) yes C114 . C115 . H1151 . 110.0 no O116 . C115 . H1151 . 109.1 no C114 . C115 . H1152 . 109.5 no O116 . C115 . H1152 . 110.5 no H1151 . C115 . H1152 . 109.6 no C115 . O116 . C117 . 117.30(15) yes O116 . C117 . C118 . 116.34(18) yes O116 . C117 . C122 . 124.4(2) yes C118 . C117 . C122 . 119.3(2) yes C117 . C118 . C119 . 120.9(2) yes C117 . C118 . H1181 . 118.1 no C119 . C118 . H1181 . 121.0 no C118 . C119 . C120 . 120.0(2) yes C118 . C119 . H1191 . 120.1 no C120 . C119 . H1191 . 119.9 no C119 . C120 . C121 . 118.8(2) yes C119 . C120 . O123 . 123.9(2) yes C121 . C120 . O123 . 117.2(2) yes C120 . C121 . C122 . 121.6(2) yes C120 . C121 . H1211 . 119.4 no C122 . C121 . H1211 . 119.0 no C117 . C122 . C121 . 119.5(2) yes C117 . C122 . H1221 . 119.1 no C121 . C122 . H1221 . 121.4 no C120 . O123 . C124 . 119.6(2) yes O123 . C124 . C125 . 109.0(3) yes O123 . C124 . H1242 . 109.8 no C125 . C124 . H1242 . 109.3 no O123 . C124 . H1241 . 109.9 no C125 . C124 . H1241 . 110.6 no H1242 . C124 . H1241 . 108.2 no C124 . C125 . O126 . 110.8(3) yes C124 . C125 . H1251 . 110.7 no O126 . C125 . H1251 . 109.3 no C124 . C125 . H1252 . 109.5 no O126 . C125 . H1252 . 104.5 no H1251 . C125 . H1252 . 111.8 no C125 . O126 . C127 . 114.0(2) yes O126 . C127 . C128 . 113.3(3) yes O126 . C127 . H1271 . 109.5 no C128 . C127 . H1271 . 109.3 no O126 . C127 . H1272 . 105.4 no C128 . C127 . H1272 . 109.0 no H1271 . C127 . H1272 . 110.3 no C127 . C128 . O129 . 108.8(2) yes C127 . C128 . H1281 . 108.9 no O129 . C128 . H1281 . 109.6 no C127 . C128 . H1282 . 112.8 no O129 . C128 . H1282 . 107.6 no H1281 . C128 . H1282 . 109.0 no C128 . O129 . C130 . 111.65(19) yes O129 . C130 . C131 . 111.24(19) yes O129 . C130 . H1302 . 107.5 no C131 . C130 . H1302 . 110.7 no O129 . C130 . H1301 . 107.1 no C131 . C130 . H1301 . 109.9 no H1302 . C130 . H1301 . 110.2 no C130 . C131 . O132 . 110.1(2) yes C130 . C131 . H1312 . 109.6 no O132 . C131 . H1312 . 108.9 no C130 . C131 . H1311 . 108.5 no O132 . C131 . H1311 . 109.5 no H1312 . C131 . H1311 . 110.3 no C131 . O132 . C133 . 111.81(18) yes O132 . C133 . C134 . 109.26(18) yes O132 . C133 . H1332 . 108.8 no C134 . C133 . H1332 . 109.8 no O132 . C133 . H1331 . 109.9 no C134 . C133 . H1331 . 108.5 no H1332 . C133 . H1331 . 110.6 no C133 . C134 . O135 . 108.57(17) yes C133 . C134 . H1342 . 110.1 no O135 . C134 . H1342 . 108.9 no C133 . C134 . H1341 . 109.9 no O135 . C134 . H1341 . 109.6 no H1342 . C134 . H1341 . 109.7 no C134 . O135 . C136 . 116.98(15) yes O135 . C136 . C137 . 116.09(17) yes O135 . C136 . C141 . 124.72(18) yes C137 . C136 . C141 . 119.18(19) yes C136 . C137 . C138 . 120.65(18) yes C136 . C137 . H1371 . 119.3 no C138 . C137 . H1371 . 120.0 no C137 . C138 . C139 . 120.10(18) yes C137 . C138 . H1381 . 120.2 no C139 . C138 . H1381 . 119.7 no C138 . C139 . C140 . 119.41(19) yes C138 . C139 . O142 . 115.89(17) yes C140 . C139 . O142 . 124.69(17) yes C139 . C140 . C141 . 120.48(18) yes C139 . C140 . H1401 . 119.8 no C141 . C140 . H1401 . 119.8 no C140 . C141 . C136 . 120.17(18) yes C140 . C141 . H1411 . 119.2 no C136 . C141 . H1411 . 120.7 no C139 . O142 . C143 . 117.09(14) yes O142 . C143 . C144 . 107.71(15) yes O142 . C143 . H1432 . 110.6 no C144 . C143 . H1432 . 110.0 no O142 . C143 . H1431 . 109.4 no C144 . C143 . H1431 . 109.7 no H1432 . C143 . H1431 . 109.4 no C143 . C144 . N145 . 112.09(15) yes C143 . C144 . H1441 . 109.4 no N145 . C144 . H1441 . 109.6 no C143 . C144 . H1442 . 108.8 no N145 . C144 . H1442 . 106.8 no H1441 . C144 . H1442 . 110.1 no C144 . N145 . C146 . 121.53(15) yes C144 . N145 . H1451 . 118.1 no C146 . N145 . H1451 . 120.4 no C102 . C146 . N145 . 117.11(15) yes C102 . C146 . O147 . 121.00(15) yes N145 . C146 . O147 . 121.86(16) yes C202 . C201 . H2011 . 109.9 no C202 . C201 . H2013 . 110.2 no H2011 . C201 . H2013 . 109.5 no C202 . C201 . H2012 . 108.6 no H2011 . C201 . H2012 . 110.1 no H2013 . C201 . H2012 . 108.5 no C201 . C202 . N203 . 179.8(3) yes C205 . C204 . H2043 . 111.3 no C205 . C204 . H2041 . 109.1 no H2043 . C204 . H2041 . 109.0 no C205 . C204 . H2042 . 108.7 no H2043 . C204 . H2042 . 109.4 no H2041 . C204 . H2042 . 109.5 no C204 . C205 . N206 . 177.8(4) yes C208 . C207 . H2071 . 108.4 no C208 . C207 . H2072 . 108.7 no H2071 . C207 . H2072 . 110.3 no C208 . C207 . H2073 . 109.6 no H2071 . C207 . H2073 . 109.3 no H2072 . C207 . H2073 . 110.5 no C207 . C208 . N209 . 176.3(8) yes C211 . C210 . H2101 . 109.1 no C211 . C210 . H2103 . 109.9 no H2101 . C210 . H2103 . 111.7 no C211 . C210 . H2102 . 106.1 no H2101 . C210 . H2102 . 109.8 no H2103 . C210 . H2102 . 110.0 no C210 . C211 . N212 . 179.6(4) yes 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 C21 . H211 . O147 . 135 0.95 2.51 3.257(4) yes C34 . H341 . O147 1_455 139 0.98 2.53 3.327(4) yes C41 . H411 . O112 1_455 139 0.95 2.37 3.146(4) yes C122 . H1221 . O47 1_655 131 0.94 2.54 3.236(4) yes C201 . H2011 . O135 1_445 139 0.97 2.58 3.375(4) yes C201 . H2012 . O35 . 161 0.97 2.59 3.521(4) yes C210 . H2101 . O29 . 158 0.97 2.40 3.326(4) yes N13 . H131 . O42 2_766 146 0.86 2.22 2.969(4) yes N145 . H1451 . O116 2_865 141 0.86 2.24 2.963(4) yes N45 . H451 . O16 2_766 143 0.85 2.24 2.963(4) yes N113 . H1131 . O142 2_865 154 0.85 2.23 3.019(4) yes #===END _chemical_name_common .