# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Marcel Mayor' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Richard Berndt' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Sandro Gabutti' '' '' 'Marco Knutzen' '' '' 'Markus Neuburger' '' '' 'Guillaume Schull' '' '' _publ_contact_author_name 'Marcel Mayor' _publ_contact_author_address ; Department of Chemistry University of Basel St. Johannsring 19 Basel CH-4056 SWITZERLAND ; _publ_contact_author_email MARCEL.MAYOR@UNIBAS.CH _publ_requested_journal 'Chemical Communications' _publ_section_title ; A rigid naphthalenebisimide cyclophane - towards surface decoupled chromophores ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_name_full ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_phone '+44 1865 000000' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' data_sg21_2 _database_code_depnum_ccdc_archive 'CCDC 673653' _audit_creation_date 07-04-11 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '4110951 sg21_2_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 17.7349(2) _cell_length_b 16.9022(2) _cell_length_c 19.1495(2) _cell_angle_alpha 90 _cell_angle_beta 92.6081(6) _cell_angle_gamma 90 _cell_volume 5734.29(11) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _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 = C48 H38 N4 O8 # Dc = 0.93 Fooo = 2259.20 Mu = 0.64 M = 798.85 # Found Formula = C68.60 H61.20 N4 O8 # Dc = 1.24 FOOO = 2259.20 Mu = 0.81 M = 1069.66 _chemical_formula_sum 'C68.60 H61.20 N4 O8' _chemical_formula_moiety 'C52 H40 N4 O8, C8 H10, 0.6(C9 H12), 0.4(C8 H10)' _chemical_compound_source ? _chemical_formula_weight 1069.66 _cell_measurement_reflns_used 27057 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _cell_measurement_temperature 173 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.32 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2259.200 _exptl_absorpt_coefficient_mu 0.081 # Sheldrick geometric approximatio 0.97 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.97 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 50388 _reflns_number_total 13631 _diffrn_reflns_av_R_equivalents 0.033 # Number of reflections with Friedels Law is 13631 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 13653 _diffrn_reflns_theta_min 3.062 _diffrn_reflns_theta_max 27.858 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.858 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -23 _reflns_limit_h_max 23 _reflns_limit_k_min 0 _reflns_limit_k_max 22 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.46 _refine_diff_density_max 1.12 _refine_ls_number_reflns 9239 _refine_ls_number_restraints 186 _refine_ls_number_parameters 802 #_refine_ls_R_factor_ref 0.0839 _refine_ls_wR_factor_ref 0.0794 _refine_ls_goodness_of_fit_ref 1.0531 #_reflns_number_all 13536 _refine_ls_R_factor_all 0.1040 _refine_ls_wR_factor_all 0.0867 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 9239 _refine_ls_R_factor_gt 0.0839 _refine_ls_wR_factor_gt 0.0794 _refine_ls_shift/su_max 0.001133 # 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 noref # 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: 1.24 -0.530 0.389 -0.723 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. 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 _atom_site_attached_hydrogens O1 O 0.15614(10) 0.71703(11) 0.58311(10) 0.0427 1.0000 Uani . . . . . . O2 O -0.00918(10) 0.42724(12) 0.36121(10) 0.0448 1.0000 Uani . . . . . . O3 O 0.21894(12) 0.37862(13) 0.27179(10) 0.0510 1.0000 Uani . . . . . . O4 O 0.38766(10) 0.65050(13) 0.50947(10) 0.0473 1.0000 Uani . . . . . . O5 O 0.32849(11) 0.23602(13) 0.37679(9) 0.0481 1.0000 Uani . . . . . . O6 O 0.49750(9) 0.50348(11) 0.61783(9) 0.0392 1.0000 Uani . . . . . . O7 O 0.34009(11) 0.41881(11) 0.78276(9) 0.0408 1.0000 Uani . . . . . . O8 O 0.19404(10) 0.12778(11) 0.54954(10) 0.0409 1.0000 Uani . . . . . . N1 N 0.27215(11) 0.68213(11) 0.54783(10) 0.0306 1.0000 Uani . . . . . . N2 N 0.10578(11) 0.39816(12) 0.32079(10) 0.0333 1.0000 Uani . . . . . . N3 N 0.26143(11) 0.18124(12) 0.46338(10) 0.0317 1.0000 Uani . . . . . . N4 N 0.41860(10) 0.46068(12) 0.70004(9) 0.0303 1.0000 Uani . . . . . . C1 C 0.21724(15) 0.66998(17) 0.84374(14) 0.0460 1.0000 Uani D U . . . . C2 C 0.2587(3) 0.6710(4) 0.9156(2) 0.1021 1.0000 Uani D U . . . . C3 C 0.1780(3) 0.7486(3) 0.8396(3) 0.0941 1.0000 Uani D U . . . . C4 C 0.1627(3) 0.6026(3) 0.8420(3) 0.0996 1.0000 Uani D U . . . . C5 C 0.27397(13) 0.65889(14) 0.78597(12) 0.0339 1.0000 Uani . . . . . . C6 C 0.26708(13) 0.70199(14) 0.72373(12) 0.0342 1.0000 Uani . . . . . . C7 C 0.31772(13) 0.69095(14) 0.67088(12) 0.0322 1.0000 Uani . . . . . . C8 C 0.37580(13) 0.63669(14) 0.67986(12) 0.0328 1.0000 Uani . . . . . . C9 C 0.38235(12) 0.59157(14) 0.74078(12) 0.0314 1.0000 Uani . . . . . . C10 C 0.33148(13) 0.60336(14) 0.79286(12) 0.0331 1.0000 Uani . . . . . . C11 C 0.30723(14) 0.73520(14) 0.60225(12) 0.0351 1.0000 Uani . . . . . . C12 C 0.19326(13) 0.67661(13) 0.54560(11) 0.0310 1.0000 Uani . . . . . . C13 C 0.15836(12) 0.61899(13) 0.49522(11) 0.0280 1.0000 Uani . . . . . . C14 C 0.08169(13) 0.60863(14) 0.49187(12) 0.0316 1.0000 Uani . . . . . . C15 C 0.04830(12) 0.55283(14) 0.44599(12) 0.0320 1.0000 Uani . . . . . . C16 C 0.09199(12) 0.50730(13) 0.40385(11) 0.0291 1.0000 Uani . . . . . . C17 C 0.05731(13) 0.44259(14) 0.36119(12) 0.0330 1.0000 Uani . . . . . . C18 C 0.18266(14) 0.41418(15) 0.31364(12) 0.0359 1.0000 Uani . . . . . . C19 C 0.21738(13) 0.47420(14) 0.36174(11) 0.0318 1.0000 Uani . . . . . . C20 C 0.29456(14) 0.48406(16) 0.36556(13) 0.0384 1.0000 Uani . . . . . . C21 C 0.32823(13) 0.53880(16) 0.41262(13) 0.0365 1.0000 Uani . . . . . . C22 C 0.28382(12) 0.58385(13) 0.45467(11) 0.0304 1.0000 Uani . . . . . . C23 C 0.32004(13) 0.64068(14) 0.50519(12) 0.0329 1.0000 Uani . . . . . . C24 C 0.20467(12) 0.57466(13) 0.45167(11) 0.0272 1.0000 Uani . . . . . . C25 C 0.17100(12) 0.51857(13) 0.40508(10) 0.0273 1.0000 Uani . . . . . . C26 C 0.07204(14) 0.33135(15) 0.28042(12) 0.0365 1.0000 Uani . . . . . . C27 C 0.07645(13) 0.25376(14) 0.32081(11) 0.0325 1.0000 Uani . . . . . . C28 C 0.01197(13) 0.20705(14) 0.32612(12) 0.0337 1.0000 Uani . . . . . . C29 C 0.01519(13) 0.13260(14) 0.35788(12) 0.0333 1.0000 Uani . . . . . . C30 C 0.08551(13) 0.10822(14) 0.38756(12) 0.0334 1.0000 Uani . . . . . . C31 C 0.14980(13) 0.15425(14) 0.38339(11) 0.0320 1.0000 Uani . . . . . . C32 C 0.14503(13) 0.22706(14) 0.34940(12) 0.0323 1.0000 Uani . . . . . . C33 C -0.05408(14) 0.07893(15) 0.36303(14) 0.0392 1.0000 Uani . . . . . . C34 C -0.08056(19) 0.0802(2) 0.43803(18) 0.0588 1.0000 Uani . . . . . . C35 C -0.11955(17) 0.1062(2) 0.3145(2) 0.0589 1.0000 Uani . . . . . . C36 C -0.03437(17) -0.00625(17) 0.3437(2) 0.0558 1.0000 Uani . . . . . . C37 C 0.22546(13) 0.12472(14) 0.41313(13) 0.0353 1.0000 Uani . . . . . . C38 C 0.23947(12) 0.17700(14) 0.53268(11) 0.0306 1.0000 Uani . . . . . . C39 C 0.27388(12) 0.23517(13) 0.58245(11) 0.0285 1.0000 Uani . . . . . . C40 C 0.25273(13) 0.23651(15) 0.65071(12) 0.0337 1.0000 Uani . . . . . . C41 C 0.28267(14) 0.29308(16) 0.69737(11) 0.0360 1.0000 Uani . . . . . . C42 C 0.33489(12) 0.34731(14) 0.67613(11) 0.0298 1.0000 Uani . . . . . . C43 C 0.36354(13) 0.40969(14) 0.72468(11) 0.0314 1.0000 Uani . . . . . . C44 C 0.44811(12) 0.45797(14) 0.63414(11) 0.0297 1.0000 Uani . . . . . . C45 C 0.41505(12) 0.39813(13) 0.58467(11) 0.0281 1.0000 Uani . . . . . . C46 C 0.43806(13) 0.39546(14) 0.51675(12) 0.0330 1.0000 Uani . . . . . . C47 C 0.40524(13) 0.34181(15) 0.46918(11) 0.0344 1.0000 Uani . . . . . . C48 C 0.35064(12) 0.28921(14) 0.48985(11) 0.0301 1.0000 Uani . . . . . . C49 C 0.31431(13) 0.23425(15) 0.43827(12) 0.0346 1.0000 Uani . . . . . . C50 C 0.32798(11) 0.28930(13) 0.55952(11) 0.0262 1.0000 Uani . . . . . . C51 C 0.35967(11) 0.34540(13) 0.60705(11) 0.0272 1.0000 Uani . . . . . . C52 C 0.44129(13) 0.52731(15) 0.74703(12) 0.0342 1.0000 Uani . . . . . . C53 C 0.15080(16) 0.42335(18) 0.62780(15) 0.0466 1.0000 Uani . . . . . . C54 C 0.10293(19) 0.3833(2) 0.66729(17) 0.0560 1.0000 Uani . . . . . . C55 C 0.06470(18) 0.32014(19) 0.64125(15) 0.0511 1.0000 Uani . . . . . . C56 C 0.07104(14) 0.29276(15) 0.57530(14) 0.0406 1.0000 Uani . . . . . . C57 C 0.11882(17) 0.3327(2) 0.53095(14) 0.0521 1.0000 Uani . . . . . . C58 C 0.16147(16) 0.40162(18) 0.55983(16) 0.0480 1.0000 Uani . . . . . . C59 C 0.1926(2) 0.4968(2) 0.6562(2) 0.0685 1.0000 Uani . . . . . . C60 C 0.0283(2) 0.2221(2) 0.5450(2) 0.0668 1.0000 Uani . . . . . . C61 C 0.4634(4) 0.6987(4) 0.2652(4) 0.0856 0.6000 Uani D U . . . . C62 C 0.4552(4) 0.7304(4) 0.3303(4) 0.0889 0.6000 Uani D U . . . . C63 C 0.4978(4) 0.7923(4) 0.3587(4) 0.0890 0.6000 Uani D U . . . . C64 C 0.5523(4) 0.8243(4) 0.3170(4) 0.0911 0.6000 Uani D U . . . . C65 C 0.5641(4) 0.7952(5) 0.2497(4) 0.0972 0.6000 Uani D U . . . . C66 C 0.5182(4) 0.7324(4) 0.2255(5) 0.0952 0.6000 Uani D U . . . . C67 C 0.4185(5) 0.6349(5) 0.2363(6) 0.0962 0.6000 Uani D U . . . . C68 C 0.4860(5) 0.8215(5) 0.4275(5) 0.1100 0.6000 Uani D U . . . . C69 C 0.5326(6) 0.8762(7) 0.4668(7) 0.1339 0.6000 Uani D U . . . . C71 C 0.4262(7) 0.6427(6) 0.2204(6) 0.1012 0.4000 Uani D U . . . . C72 C 0.3692(6) 0.5892(6) 0.1998(6) 0.1063 0.4000 Uani D U . . . . C73 C 0.3707(7) 0.5536(6) 0.1340(6) 0.1177 0.4000 Uani D U . . . . C74 C 0.4291(7) 0.5710(6) 0.0904(6) 0.1224 0.4000 Uani D U . . . . C75 C 0.4848(7) 0.6239(7) 0.1110(7) 0.1289 0.4000 Uani D U . . . . C76 C 0.4829(6) 0.6603(6) 0.1752(6) 0.1130 0.4000 Uani D U . . . . C77 C 0.4255(8) 0.6798(7) 0.2889(6) 0.0935 0.4000 Uani D U . . . . C78 C 0.3104(8) 0.5000(7) 0.1131(9) 0.1362 0.4000 Uani D U . . . . H21 H 0.2867 0.6218 0.9228 0.1232 1.0000 Uiso . . . . . . H22 H 0.2927 0.7159 0.9172 0.1232 1.0000 Uiso . . . . . . H23 H 0.2218 0.6771 0.9520 0.1232 1.0000 Uiso . . . . . . H31 H 0.1489 0.7531 0.7952 0.1152 1.0000 Uiso . . . . . . H32 H 0.2154 0.7900 0.8422 0.1152 1.0000 Uiso . . . . . . H33 H 0.1440 0.7531 0.8773 0.1152 1.0000 Uiso . . . . . . H41 H 0.1340 0.6077 0.7977 0.1223 1.0000 Uiso . . . . . . H42 H 0.1285 0.6061 0.8795 0.1223 1.0000 Uiso . . . . . . H43 H 0.1903 0.5532 0.8440 0.1223 1.0000 Uiso . . . . . . H61 H 0.2272 0.7381 0.7171 0.0411 1.0000 Uiso . . . . . . H81 H 0.4117 0.6305 0.6444 0.0395 1.0000 Uiso . . . . . . H101 H 0.3373 0.5737 0.8347 0.0399 1.0000 Uiso . . . . . . H111 H 0.2752 0.7795 0.6069 0.0422 1.0000 Uiso . . . . . . H112 H 0.3560 0.7518 0.5867 0.0422 1.0000 Uiso . . . . . . H141 H 0.0517 0.6389 0.5219 0.0381 1.0000 Uiso . . . . . . H151 H -0.0042 0.5467 0.4443 0.0385 1.0000 Uiso . . . . . . H201 H 0.3248 0.4530 0.3366 0.0465 1.0000 Uiso . . . . . . H211 H 0.3807 0.5455 0.4154 0.0441 1.0000 Uiso . . . . . . H261 H 0.0195 0.3427 0.2678 0.0436 1.0000 Uiso . . . . . . H262 H 0.0999 0.3267 0.2381 0.0436 1.0000 Uiso . . . . . . H281 H -0.0343 0.2255 0.3074 0.0406 1.0000 Uiso . . . . . . H301 H 0.0887 0.0591 0.4117 0.0402 1.0000 Uiso . . . . . . H321 H 0.1883 0.2573 0.3450 0.0390 1.0000 Uiso . . . . . . H341 H -0.1222 0.0440 0.4428 0.0710 1.0000 Uiso . . . . . . H342 H -0.0956 0.1329 0.4500 0.0710 1.0000 Uiso . . . . . . H343 H -0.0396 0.0639 0.4702 0.0710 1.0000 Uiso . . . . . . H351 H -0.1616 0.0700 0.3194 0.0703 1.0000 Uiso . . . . . . H352 H -0.1338 0.1595 0.3258 0.0703 1.0000 Uiso . . . . . . H353 H -0.1028 0.1043 0.2675 0.0703 1.0000 Uiso . . . . . . H361 H -0.0783 -0.0374 0.3478 0.0670 1.0000 Uiso . . . . . . H362 H 0.0044 -0.0260 0.3763 0.0670 1.0000 Uiso . . . . . . H363 H -0.0180 -0.0077 0.2968 0.0670 1.0000 Uiso . . . . . . H371 H 0.2186 0.0745 0.4370 0.0423 1.0000 Uiso . . . . . . H372 H 0.2596 0.1175 0.3760 0.0423 1.0000 Uiso . . . . . . H401 H 0.2185 0.1990 0.6657 0.0406 1.0000 Uiso . . . . . . H411 H 0.2679 0.2931 0.7439 0.0434 1.0000 Uiso . . . . . . H461 H 0.4758 0.4291 0.5025 0.0400 1.0000 Uiso . . . . . . H471 H 0.4194 0.3435 0.4230 0.0418 1.0000 Uiso . . . . . . H521 H 0.4459 0.5083 0.7942 0.0410 1.0000 Uiso . . . . . . H522 H 0.4897 0.5469 0.7331 0.0410 1.0000 Uiso . . . . . . H541 H 0.0957 0.3999 0.7154 0.0673 1.0000 Uiso . . . . . . H551 H 0.0312 0.2927 0.6705 0.0614 1.0000 Uiso . . . . . . H571 H 0.1231 0.3150 0.4852 0.0631 1.0000 Uiso . . . . . . H581 H 0.1942 0.4295 0.5328 0.0579 1.0000 Uiso . . . . . . H591 H 0.2326 0.5123 0.6262 0.0819 1.0000 Uiso . . . . . . H592 H 0.2136 0.4833 0.7021 0.0819 1.0000 Uiso . . . . . . H593 H 0.1590 0.5403 0.6602 0.0819 1.0000 Uiso . . . . . . H601 H 0.0407 0.2139 0.4962 0.0805 1.0000 Uiso . . . . . . H602 H 0.0413 0.1742 0.5708 0.0805 1.0000 Uiso . . . . . . H603 H -0.0260 0.2301 0.5467 0.0805 1.0000 Uiso . . . . . . H621 H 0.4180 0.7082 0.3581 0.1062 0.6000 Uiso . . . . . . H641 H 0.5816 0.8665 0.3356 0.1094 0.6000 Uiso . . . . . . H651 H 0.6015 0.8171 0.2221 0.1170 0.6000 Uiso . . . . . . H661 H 0.5234 0.7119 0.1806 0.1138 0.6000 Uiso . . . . . . H671 H 0.4332 0.6285 0.1882 0.1141 0.6000 Uiso . . . . . . H672 H 0.3664 0.6488 0.2381 0.1141 0.6000 Uiso . . . . . . H673 H 0.4301 0.5880 0.2627 0.1141 0.6000 Uiso . . . . . . H681 H 0.4366 0.8458 0.4253 0.1323 0.6000 Uiso . . . . . . H682 H 0.4854 0.7747 0.4568 0.1323 0.6000 Uiso . . . . . . H691 H 0.5132 0.8827 0.5139 0.1611 0.6000 Uiso . . . . . . H692 H 0.5331 0.9268 0.4433 0.1611 0.6000 Uiso . . . . . . H693 H 0.5836 0.8544 0.4717 0.1611 0.6000 Uiso . . . . . . H721 H 0.3308 0.5772 0.2287 0.1267 0.4000 Uiso . . . . . . H741 H 0.4313 0.5469 0.0467 0.1467 0.4000 Uiso . . . . . . H751 H 0.5241 0.6352 0.0808 0.1539 0.4000 Uiso . . . . . . H761 H 0.5189 0.6970 0.1884 0.1346 0.4000 Uiso . . . . . . H771 H 0.4734 0.7054 0.2984 0.1111 0.4000 Uiso . . . . . . H772 H 0.3859 0.7178 0.2894 0.1111 0.4000 Uiso . . . . . . H773 H 0.4181 0.6409 0.3238 0.1111 0.4000 Uiso . . . . . . H781 H 0.3297 0.4673 0.0752 0.1616 0.4000 Uiso . . . . . . H782 H 0.2677 0.5293 0.0958 0.1616 0.4000 Uiso . . . . . . H783 H 0.2987 0.4672 0.1515 0.1616 0.4000 Uiso . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0383(9) 0.0419(10) 0.0482(10) -0.0162(8) 0.0044(7) 0.0070(7) O2 0.0348(9) 0.0496(11) 0.0498(10) -0.0102(8) 0.0000(7) -0.0050(8) O3 0.0539(11) 0.0536(11) 0.0470(10) -0.0200(9) 0.0185(9) -0.0067(9) O4 0.0295(8) 0.0628(12) 0.0498(10) -0.0130(9) 0.0035(7) -0.0057(8) O5 0.0506(11) 0.0625(12) 0.0319(9) -0.0099(8) 0.0104(8) -0.0137(9) O6 0.0306(8) 0.0434(10) 0.0444(9) -0.0067(7) 0.0104(7) -0.0065(7) O7 0.0500(10) 0.0450(10) 0.0281(8) -0.0013(7) 0.0090(7) -0.0031(8) O8 0.0389(9) 0.0396(9) 0.0443(9) 0.0021(7) 0.0031(7) -0.0095(8) N1 0.0303(9) 0.0312(9) 0.0302(9) -0.0011(7) 0.0012(7) 0.0000(7) N2 0.0388(10) 0.0311(10) 0.0298(9) -0.0035(7) -0.0001(8) -0.0016(8) N3 0.0276(9) 0.0334(10) 0.0340(9) -0.0014(7) -0.0003(7) 0.0003(7) N4 0.0266(9) 0.0344(10) 0.0299(9) -0.0022(7) 0.0014(7) 0.0013(7) C1 0.0440(13) 0.0495(15) 0.0458(13) -0.0069(11) 0.0180(11) 0.0018(11) C2 0.088(3) 0.167(5) 0.053(2) -0.021(3) 0.0154(19) 0.026(3) C3 0.123(3) 0.071(2) 0.094(3) -0.001(2) 0.064(3) 0.027(2) C4 0.094(3) 0.095(3) 0.115(3) -0.040(3) 0.063(3) -0.037(3) C5 0.0302(10) 0.0357(12) 0.0360(11) -0.0082(9) 0.0051(9) -0.0038(9) C6 0.0315(11) 0.0324(11) 0.0386(12) -0.0072(9) 0.0005(9) -0.0007(9) C7 0.0310(10) 0.0321(11) 0.0332(10) -0.0045(9) -0.0009(8) -0.0044(9) C8 0.0286(10) 0.0368(12) 0.0331(11) -0.0052(9) 0.0019(8) -0.0023(9) C9 0.0276(10) 0.0347(11) 0.0319(10) -0.0067(9) -0.0007(8) -0.0014(9) C10 0.0335(11) 0.0344(11) 0.0314(10) -0.0050(9) 0.0010(8) -0.0035(9) C11 0.0370(11) 0.0323(11) 0.0358(11) -0.0028(9) -0.0010(9) -0.0033(9) C12 0.0330(11) 0.0295(11) 0.0305(10) -0.0012(8) 0.0011(8) 0.0017(9) C13 0.0295(10) 0.0275(10) 0.0270(9) -0.0002(8) 0.0019(8) 0.0041(8) C14 0.0299(10) 0.0328(11) 0.0323(10) -0.0004(9) 0.0045(8) 0.0056(9) C15 0.0251(10) 0.0365(11) 0.0344(11) 0.0013(9) 0.0009(8) 0.0036(9) C16 0.0290(10) 0.0305(10) 0.0276(9) 0.0024(8) -0.0004(8) 0.0030(8) C17 0.0343(11) 0.0341(11) 0.0304(10) 0.0013(9) 0.0002(8) 0.0001(9) C18 0.0416(12) 0.0347(12) 0.0319(11) -0.0037(9) 0.0071(9) -0.0010(10) C19 0.0353(11) 0.0306(11) 0.0299(10) -0.0018(8) 0.0063(8) 0.0014(9) C20 0.0346(11) 0.0438(13) 0.0376(12) -0.0068(10) 0.0110(9) 0.0049(10) C21 0.0271(10) 0.0448(13) 0.0382(12) -0.0029(10) 0.0068(9) 0.0018(9) C22 0.0283(10) 0.0322(11) 0.0310(10) 0.0018(8) 0.0034(8) 0.0009(8) C23 0.0309(11) 0.0362(12) 0.0318(10) -0.0004(9) 0.0042(8) -0.0003(9) C24 0.0270(10) 0.0292(10) 0.0257(9) 0.0014(8) 0.0036(7) 0.0024(8) C25 0.0293(10) 0.0272(10) 0.0258(9) 0.0021(8) 0.0036(8) 0.0017(8) C26 0.0443(13) 0.0326(11) 0.0319(11) -0.0040(9) -0.0046(9) -0.0035(10) C27 0.0391(11) 0.0307(11) 0.0277(10) -0.0060(8) 0.0012(8) 0.0009(9) C28 0.0348(11) 0.0328(11) 0.0333(11) -0.0050(9) -0.0017(9) 0.0028(9) C29 0.0313(11) 0.0337(11) 0.0347(11) -0.0072(9) 0.0009(8) 0.0015(9) C30 0.0335(11) 0.0325(11) 0.0340(11) -0.0026(9) 0.0012(9) 0.0015(9) C31 0.0318(11) 0.0355(12) 0.0288(10) -0.0066(8) 0.0009(8) 0.0027(9) C32 0.0333(11) 0.0333(11) 0.0305(10) -0.0063(8) 0.0015(8) -0.0028(9) C33 0.0330(11) 0.0331(12) 0.0512(14) -0.0020(10) -0.0002(10) 0.0005(10) C34 0.0519(17) 0.0646(19) 0.0609(18) -0.0039(15) 0.0149(14) -0.0149(15) C35 0.0386(14) 0.0542(17) 0.082(2) 0.0071(16) -0.0144(14) -0.0051(13) C36 0.0404(14) 0.0358(14) 0.091(2) -0.0128(14) -0.0044(14) -0.0031(11) C37 0.0331(11) 0.0334(12) 0.0391(12) -0.0068(9) -0.0008(9) 0.0026(9) C38 0.0243(10) 0.0328(11) 0.0342(11) 0.0037(9) -0.0020(8) 0.0028(8) C39 0.0243(9) 0.0310(10) 0.0300(10) 0.0052(8) 0.0008(8) 0.0026(8) C40 0.0302(10) 0.0399(12) 0.0310(10) 0.0080(9) 0.0033(8) -0.0051(9) C41 0.0379(12) 0.0441(13) 0.0264(10) 0.0046(9) 0.0051(9) -0.0039(10) C42 0.0273(10) 0.0362(11) 0.0261(10) 0.0041(8) 0.0029(8) 0.0023(8) C43 0.0306(10) 0.0362(11) 0.0274(10) 0.0037(8) 0.0021(8) 0.0021(9) C44 0.0229(9) 0.0335(11) 0.0329(10) 0.0001(9) 0.0038(8) 0.0023(8) C45 0.0229(9) 0.0311(11) 0.0304(10) 0.0010(8) 0.0032(8) 0.0016(8) C46 0.0293(10) 0.0353(11) 0.0352(11) 0.0011(9) 0.0103(9) -0.0030(9) C47 0.0318(11) 0.0433(13) 0.0290(10) 0.0005(9) 0.0108(8) -0.0005(9) C48 0.0275(10) 0.0330(11) 0.0300(10) 0.0008(8) 0.0040(8) 0.0041(8) C49 0.0311(10) 0.0406(13) 0.0326(11) -0.0019(9) 0.0045(8) 0.0005(10) C50 0.0206(9) 0.0307(10) 0.0274(9) 0.0025(8) 0.0017(7) 0.0038(8) C51 0.0220(9) 0.0326(11) 0.0271(9) 0.0031(8) 0.0025(7) 0.0034(8) C52 0.0293(10) 0.0404(12) 0.0323(11) -0.0057(9) -0.0024(8) 0.0016(9) C53 0.0420(14) 0.0488(15) 0.0477(14) -0.0035(12) -0.0126(11) 0.0125(12) C54 0.0550(17) 0.0645(19) 0.0481(15) 0.0046(14) -0.0038(13) 0.0083(15) C55 0.0525(16) 0.0581(17) 0.0426(14) 0.0066(13) 0.0026(12) 0.0148(14) C56 0.0329(11) 0.0373(12) 0.0511(14) 0.0029(11) -0.0026(10) 0.0070(10) C57 0.0482(15) 0.0694(19) 0.0391(13) 0.0079(13) 0.0042(11) 0.0266(14) C58 0.0423(14) 0.0489(16) 0.0530(15) 0.0176(12) 0.0052(12) 0.0112(12) C59 0.0618(19) 0.058(2) 0.084(2) -0.0077(17) -0.0196(17) 0.0020(16) C60 0.0538(18) 0.0514(18) 0.094(3) -0.0069(17) -0.0056(17) 0.0015(15) C61 0.075(4) 0.069(4) 0.110(4) 0.011(3) -0.021(3) 0.020(3) C62 0.078(4) 0.076(4) 0.111(4) 0.011(3) -0.016(4) 0.028(3) C63 0.071(3) 0.080(4) 0.114(4) 0.021(3) -0.012(3) 0.025(3) C64 0.064(3) 0.084(4) 0.124(4) 0.035(4) -0.009(3) 0.024(3) C65 0.073(4) 0.094(4) 0.123(5) 0.025(4) -0.005(4) 0.030(3) C66 0.072(4) 0.086(4) 0.126(5) 0.034(4) -0.009(3) 0.032(3) C67 0.085(5) 0.069(4) 0.131(7) 0.008(5) -0.036(5) 0.016(4) C68 0.104(5) 0.101(5) 0.123(5) 0.014(4) -0.017(4) 0.039(4) C69 0.107(6) 0.116(7) 0.177(8) 0.014(6) -0.008(6) 0.020(5) C71 0.107(6) 0.080(6) 0.114(6) 0.024(5) -0.024(5) 0.054(5) C72 0.115(6) 0.077(5) 0.124(6) 0.023(5) -0.019(6) 0.048(5) C73 0.125(6) 0.082(6) 0.143(7) 0.008(5) -0.032(5) 0.042(5) C74 0.149(7) 0.097(6) 0.120(7) 0.015(6) -0.014(6) 0.075(5) C75 0.135(7) 0.119(7) 0.131(7) 0.030(6) -0.020(6) 0.071(6) C76 0.104(6) 0.105(6) 0.127(7) 0.034(5) -0.017(5) 0.072(5) C77 0.091(7) 0.074(6) 0.114(7) 0.025(6) -0.016(6) 0.041(6) C78 0.122(8) 0.107(8) 0.176(10) -0.011(8) -0.035(8) 0.035(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5221(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 O1 . C12 . 1.208(3) yes O2 . C17 . 1.207(3) yes O3 . C18 . 1.210(3) yes O4 . C23 . 1.210(3) yes O5 . C49 . 1.215(3) yes O6 . C44 . 1.217(3) yes O7 . C43 . 1.215(3) yes O8 . C38 . 1.212(3) yes N1 . C11 . 1.490(3) yes N1 . C12 . 1.401(3) yes N1 . C23 . 1.394(3) yes N2 . C17 . 1.401(3) yes N2 . C18 . 1.403(3) yes N2 . C26 . 1.479(3) yes N3 . C37 . 1.480(3) yes N3 . C38 . 1.402(3) yes N3 . C49 . 1.398(3) yes N4 . C43 . 1.400(3) yes N4 . C44 . 1.389(3) yes N4 . C52 . 1.486(3) yes C1 . C2 . 1.529(5) yes C1 . C3 . 1.500(5) yes C1 . C4 . 1.493(5) yes C1 . C5 . 1.540(3) yes C2 . H21 . 0.975 no C2 . H22 . 0.970 no C2 . H23 . 0.984 no C3 . H31 . 0.978 no C3 . H32 . 0.963 no C3 . H33 . 0.965 no C4 . H41 . 0.974 no C4 . H42 . 0.962 no C4 . H43 . 0.968 no C5 . C6 . 1.397(3) yes C5 . C10 . 1.388(3) yes C6 . C7 . 1.396(3) yes C6 . H61 . 0.938 no C7 . C8 . 1.384(3) yes C7 . C11 . 1.516(3) yes C8 . C9 . 1.394(3) yes C8 . H81 . 0.957 no C9 . C10 . 1.389(3) yes C9 . C52 . 1.508(3) yes C10 . H101 . 0.947 no C11 . H111 . 0.946 no C11 . H112 . 0.969 no C12 . C13 . 1.486(3) yes C13 . C14 . 1.370(3) yes C13 . C24 . 1.412(3) yes C14 . C15 . 1.402(3) yes C14 . H141 . 0.949 no C15 . C16 . 1.379(3) yes C15 . H151 . 0.936 no C16 . C17 . 1.482(3) yes C16 . C25 . 1.413(3) yes C18 . C19 . 1.485(3) yes C19 . C20 . 1.377(3) yes C19 . C25 . 1.411(3) yes C20 . C21 . 1.406(4) yes C20 . H201 . 0.947 no C21 . C22 . 1.381(3) yes C21 . H211 . 0.937 no C22 . C23 . 1.488(3) yes C22 . C24 . 1.411(3) yes C24 . C25 . 1.415(3) yes C26 . C27 . 1.523(3) yes C26 . H261 . 0.971 no C26 . H262 . 0.972 no C27 . C28 . 1.397(3) yes C27 . C32 . 1.386(3) yes C28 . C29 . 1.398(3) yes C28 . H281 . 0.934 no C29 . C30 . 1.408(3) yes C29 . C33 . 1.534(3) yes C30 . C31 . 1.386(3) yes C30 . H301 . 0.951 no C31 . C32 . 1.393(3) yes C31 . C37 . 1.518(3) yes C32 . H321 . 0.930 no C33 . C34 . 1.531(4) yes C33 . C35 . 1.525(4) yes C33 . C36 . 1.531(4) yes C34 . H341 . 0.967 no C34 . H342 . 0.961 no C34 . H343 . 0.971 no C35 . H351 . 0.973 no C35 . H352 . 0.962 no C35 . H353 . 0.962 no C36 . H361 . 0.946 no C36 . H362 . 0.967 no C36 . H363 . 0.957 no C37 . H371 . 0.975 no C37 . H372 . 0.962 no C38 . C39 . 1.481(3) yes C39 . C40 . 1.376(3) yes C39 . C50 . 1.410(3) yes C40 . C41 . 1.397(3) yes C40 . H401 . 0.932 no C41 . C42 . 1.377(3) yes C41 . H411 . 0.939 no C42 . C43 . 1.480(3) yes C42 . C51 . 1.413(3) yes C44 . C45 . 1.488(3) yes C45 . C46 . 1.382(3) yes C45 . C51 . 1.407(3) yes C46 . C47 . 1.394(3) yes C46 . H461 . 0.929 no C47 . C48 . 1.385(3) yes C47 . H471 . 0.930 no C48 . C49 . 1.482(3) yes C48 . C50 . 1.411(3) yes C50 . C51 . 1.413(3) yes C52 . H521 . 0.959 no C52 . H522 . 0.970 no C53 . C54 . 1.345(5) yes C53 . C58 . 1.374(4) yes C53 . C59 . 1.533(5) yes C54 . C55 . 1.348(5) yes C54 . H541 . 0.977 no C55 . C56 . 1.355(4) yes C55 . H551 . 0.955 no C56 . C57 . 1.400(4) yes C56 . C60 . 1.516(4) yes C57 . C58 . 1.483(5) yes C57 . H571 . 0.932 no C58 . H581 . 0.924 no C59 . H591 . 0.971 no C59 . H592 . 0.966 no C59 . H593 . 0.951 no C60 . H601 . 0.980 no C60 . H602 . 0.970 no C60 . H603 . 0.974 no C61 . C62 . 1.370(8) yes C61 . C66 . 1.383(8) yes C61 . C67 . 1.436(8) yes C62 . C63 . 1.388(8) yes C62 . H621 . 0.943 no C63 . C64 . 1.392(8) yes C63 . C68 . 1.430(8) yes C64 . C65 . 1.404(8) yes C64 . H641 . 0.942 no C65 . C66 . 1.404(8) yes C65 . H651 . 0.942 no C66 . H661 . 0.936 no C67 . H671 . 0.974 no C67 . H672 . 0.956 no C67 . H673 . 0.959 no C68 . C69 . 1.431(9) yes C68 . H681 . 0.967 no C68 . H682 . 0.970 no C69 . H691 . 0.987 no C69 . H692 . 0.966 no C69 . H693 . 0.977 no C71 . C72 . 1.399(9) yes C71 . C76 . 1.389(9) yes C71 . C77 . 1.454(9) yes C72 . C73 . 1.399(9) yes C72 . H721 . 0.920 no C73 . C74 . 1.391(9) yes C73 . C78 . 1.444(9) yes C74 . C75 . 1.377(9) yes C74 . H741 . 0.933 no C75 . C76 . 1.377(9) yes C75 . H751 . 0.944 no C76 . H761 . 0.918 no C77 . H771 . 0.962 no C77 . H772 . 0.952 no C77 . H773 . 0.952 no C78 . H781 . 0.987 no C78 . H782 . 0.951 no C78 . H783 . 0.951 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 C11 . N1 . C12 . 116.49(18) yes C11 . N1 . C23 . 117.80(18) yes C12 . N1 . C23 . 125.67(19) yes C17 . N2 . C18 . 125.03(19) yes C17 . N2 . C26 . 117.00(19) yes C18 . N2 . C26 . 117.92(19) yes C37 . N3 . C38 . 116.91(19) yes C37 . N3 . C49 . 117.78(19) yes C38 . N3 . C49 . 125.31(19) yes C43 . N4 . C44 . 125.68(19) yes C43 . N4 . C52 . 115.87(18) yes C44 . N4 . C52 . 118.19(18) yes C2 . C1 . C3 . 103.9(4) yes C2 . C1 . C4 . 108.2(4) yes C3 . C1 . C4 . 112.1(4) yes C2 . C1 . C5 . 110.2(3) yes C3 . C1 . C5 . 112.7(3) yes C4 . C1 . C5 . 109.6(2) yes C1 . C2 . H21 . 109.9 no C1 . C2 . H22 . 108.1 no H21 . C2 . H22 . 110.4 no C1 . C2 . H23 . 109.4 no H21 . C2 . H23 . 109.9 no H22 . C2 . H23 . 109.2 no C1 . C3 . H31 . 109.9 no C1 . C3 . H32 . 109.0 no H31 . C3 . H32 . 108.9 no C1 . C3 . H33 . 109.5 no H31 . C3 . H33 . 108.7 no H32 . C3 . H33 . 110.8 no C1 . C4 . H41 . 105.4 no C1 . C4 . H42 . 111.5 no H41 . C4 . H42 . 108.8 no C1 . C4 . H43 . 109.3 no H41 . C4 . H43 . 110.6 no H42 . C4 . H43 . 111.1 no C1 . C5 . C6 . 121.0(2) yes C1 . C5 . C10 . 121.0(2) yes C6 . C5 . C10 . 118.0(2) yes C5 . C6 . C7 . 121.0(2) yes C5 . C6 . H61 . 119.4 no C7 . C6 . H61 . 119.6 no C6 . C7 . C8 . 119.9(2) yes C6 . C7 . C11 . 120.3(2) yes C8 . C7 . C11 . 119.7(2) yes C7 . C8 . C9 . 120.0(2) yes C7 . C8 . H81 . 120.0 no C9 . C8 . H81 . 120.1 no C8 . C9 . C10 . 119.3(2) yes C8 . C9 . C52 . 119.4(2) yes C10 . C9 . C52 . 121.1(2) yes C9 . C10 . C5 . 121.8(2) yes C9 . C10 . H101 . 118.8 no C5 . C10 . H101 . 119.3 no C7 . C11 . N1 . 109.89(19) yes C7 . C11 . H111 . 111.0 no N1 . C11 . H111 . 108.0 no C7 . C11 . H112 . 109.5 no N1 . C11 . H112 . 108.0 no H111 . C11 . H112 . 110.3 no N1 . C12 . O1 . 121.0(2) yes N1 . C12 . C13 . 116.69(18) yes O1 . C12 . C13 . 122.3(2) yes C12 . C13 . C14 . 119.83(19) yes C12 . C13 . C24 . 119.67(19) yes C14 . C13 . C24 . 120.5(2) yes C13 . C14 . C15 . 120.37(19) yes C13 . C14 . H141 . 119.0 no C15 . C14 . H141 . 120.6 no C14 . C15 . C16 . 120.7(2) yes C14 . C15 . H151 . 119.2 no C16 . C15 . H151 . 120.1 no C15 . C16 . C17 . 120.3(2) yes C15 . C16 . C25 . 119.9(2) yes C17 . C16 . C25 . 119.66(19) yes C16 . C17 . N2 . 116.78(19) yes C16 . C17 . O2 . 122.6(2) yes N2 . C17 . O2 . 120.6(2) yes N2 . C18 . O3 . 121.1(2) yes N2 . C18 . C19 . 116.66(19) yes O3 . C18 . C19 . 122.2(2) yes C18 . C19 . C20 . 119.9(2) yes C18 . C19 . C25 . 119.5(2) yes C20 . C19 . C25 . 120.6(2) yes C19 . C20 . C21 . 120.4(2) yes C19 . C20 . H201 . 119.3 no C21 . C20 . H201 . 120.3 no C20 . C21 . C22 . 120.0(2) yes C20 . C21 . H211 . 120.5 no C22 . C21 . H211 . 119.5 no C21 . C22 . C23 . 119.6(2) yes C21 . C22 . C24 . 120.6(2) yes C23 . C22 . C24 . 119.79(19) yes C22 . C23 . N1 . 116.67(19) yes C22 . C23 . O4 . 122.0(2) yes N1 . C23 . O4 . 121.3(2) yes C13 . C24 . C22 . 121.5(2) yes C13 . C24 . C25 . 119.19(19) yes C22 . C24 . C25 . 119.34(19) yes C24 . C25 . C16 . 119.37(19) yes C24 . C25 . C19 . 119.10(19) yes C16 . C25 . C19 . 121.5(2) yes N2 . C26 . C27 . 112.45(18) yes N2 . C26 . H261 . 109.8 no C27 . C26 . H261 . 108.9 no N2 . C26 . H262 . 106.8 no C27 . C26 . H262 . 109.7 no H261 . C26 . H262 . 109.1 no C26 . C27 . C28 . 120.0(2) yes C26 . C27 . C32 . 120.3(2) yes C28 . C27 . C32 . 119.6(2) yes C27 . C28 . C29 . 121.5(2) yes C27 . C28 . H281 . 119.4 no C29 . C28 . H281 . 119.1 no C28 . C29 . C30 . 117.2(2) yes C28 . C29 . C33 . 122.9(2) yes C30 . C29 . C33 . 119.9(2) yes C29 . C30 . C31 . 121.9(2) yes C29 . C30 . H301 . 118.9 no C31 . C30 . H301 . 119.2 no C30 . C31 . C32 . 119.4(2) yes C30 . C31 . C37 . 120.6(2) yes C32 . C31 . C37 . 120.0(2) yes C31 . C32 . C27 . 120.4(2) yes C31 . C32 . H321 . 119.7 no C27 . C32 . H321 . 119.9 no C29 . C33 . C34 . 109.4(2) yes C29 . C33 . C35 . 111.8(2) yes C34 . C33 . C35 . 108.0(3) yes C29 . C33 . C36 . 110.4(2) yes C34 . C33 . C36 . 108.8(3) yes C35 . C33 . C36 . 108.3(2) yes C33 . C34 . H341 . 110.4 no C33 . C34 . H342 . 109.7 no H341 . C34 . H342 . 110.1 no C33 . C34 . H343 . 109.7 no H341 . C34 . H343 . 108.2 no H342 . C34 . H343 . 108.6 no C33 . C35 . H351 . 108.5 no C33 . C35 . H352 . 110.3 no H351 . C35 . H352 . 110.8 no C33 . C35 . H353 . 107.5 no H351 . C35 . H353 . 109.9 no H352 . C35 . H353 . 109.7 no C33 . C36 . H361 . 107.8 no C33 . C36 . H362 . 109.5 no H361 . C36 . H362 . 108.6 no C33 . C36 . H363 . 109.5 no H361 . C36 . H363 . 110.4 no H362 . C36 . H363 . 111.1 no C31 . C37 . N3 . 112.28(19) yes C31 . C37 . H371 . 109.6 no N3 . C37 . H371 . 108.5 no C31 . C37 . H372 . 109.9 no N3 . C37 . H372 . 107.2 no H371 . C37 . H372 . 109.3 no N3 . C38 . O8 . 120.3(2) yes N3 . C38 . C39 . 116.81(19) yes O8 . C38 . C39 . 122.9(2) yes C38 . C39 . C40 . 120.0(2) yes C38 . C39 . C50 . 119.76(19) yes C40 . C39 . C50 . 120.2(2) yes C39 . C40 . C41 . 120.4(2) yes C39 . C40 . H401 . 119.4 no C41 . C40 . H401 . 120.2 no C40 . C41 . C42 . 120.5(2) yes C40 . C41 . H411 . 119.5 no C42 . C41 . H411 . 120.0 no C41 . C42 . C43 . 120.30(19) yes C41 . C42 . C51 . 120.2(2) yes C43 . C42 . C51 . 119.46(19) yes C42 . C43 . N4 . 116.83(18) yes C42 . C43 . O7 . 122.9(2) yes N4 . C43 . O7 . 120.2(2) yes N4 . C44 . O6 . 121.2(2) yes N4 . C44 . C45 . 116.56(18) yes O6 . C44 . C45 . 122.24(19) yes C44 . C45 . C46 . 119.80(19) yes C44 . C45 . C51 . 119.79(19) yes C46 . C45 . C51 . 120.4(2) yes C45 . C46 . C47 . 120.3(2) yes C45 . C46 . H461 . 120.3 no C47 . C46 . H461 . 119.5 no C46 . C47 . C48 . 120.5(2) yes C46 . C47 . H471 . 118.6 no C48 . C47 . H471 . 120.9 no C47 . C48 . C49 . 120.0(2) yes C47 . C48 . C50 . 120.2(2) yes C49 . C48 . C50 . 119.8(2) yes C48 . C49 . N3 . 116.78(19) yes C48 . C49 . O5 . 121.8(2) yes N3 . C49 . O5 . 121.4(2) yes C48 . C50 . C39 . 121.4(2) yes C48 . C50 . C51 . 119.19(19) yes C39 . C50 . C51 . 119.41(19) yes C50 . C51 . C42 . 119.12(19) yes C50 . C51 . C45 . 119.44(19) yes C42 . C51 . C45 . 121.4(2) yes C9 . C52 . N4 . 109.28(17) yes C9 . C52 . H521 . 110.2 no N4 . C52 . H521 . 109.0 no C9 . C52 . H522 . 110.6 no N4 . C52 . H522 . 108.1 no H521 . C52 . H522 . 109.6 no C54 . C53 . C58 . 121.1(3) yes C54 . C53 . C59 . 121.0(3) yes C58 . C53 . C59 . 117.9(3) yes C53 . C54 . C55 . 120.7(3) yes C53 . C54 . H541 . 119.9 no C55 . C54 . H541 . 119.4 no C54 . C55 . C56 . 123.6(3) yes C54 . C55 . H551 . 119.0 no C56 . C55 . H551 . 117.4 no C55 . C56 . C57 . 118.6(3) yes C55 . C56 . C60 . 124.4(3) yes C57 . C56 . C60 . 117.0(3) yes C56 . C57 . C58 . 117.7(3) yes C56 . C57 . H571 . 119.5 no C58 . C57 . H571 . 122.8 no C57 . C58 . C53 . 118.3(3) yes C57 . C58 . H581 . 121.0 no C53 . C58 . H581 . 120.8 no C53 . C59 . H591 . 111.2 no C53 . C59 . H592 . 107.0 no H591 . C59 . H592 . 109.9 no C53 . C59 . H593 . 111.1 no H591 . C59 . H593 . 108.5 no H592 . C59 . H593 . 109.1 no C56 . C60 . H601 . 110.2 no C56 . C60 . H602 . 111.2 no H601 . C60 . H602 . 108.0 no C56 . C60 . H603 . 110.8 no H601 . C60 . H603 . 108.5 no H602 . C60 . H603 . 108.1 no C62 . C61 . C66 . 116.5(8) yes C62 . C61 . C67 . 124.4(9) yes C66 . C61 . C67 . 119.1(9) yes C61 . C62 . C63 . 124.9(8) yes C61 . C62 . H621 . 117.6 no C63 . C62 . H621 . 117.5 no C62 . C63 . C64 . 116.6(8) yes C62 . C63 . C68 . 121.4(8) yes C64 . C63 . C68 . 121.9(8) yes C63 . C64 . C65 . 121.8(8) yes C63 . C64 . H641 . 117.6 no C65 . C64 . H641 . 120.6 no C64 . C65 . C66 . 117.3(8) yes C64 . C65 . H651 . 121.0 no C66 . C65 . H651 . 121.7 no C65 . C66 . C61 . 122.8(8) yes C65 . C66 . H661 . 120.1 no C61 . C66 . H661 . 117.1 no C61 . C67 . H671 . 106.3 no C61 . C67 . H672 . 108.8 no H671 . C67 . H672 . 111.3 no C61 . C67 . H673 . 108.4 no H671 . C67 . H673 . 110.2 no H672 . C67 . H673 . 111.6 no C63 . C68 . C69 . 127.0(10) yes C63 . C68 . H681 . 105.9 no C69 . C68 . H681 . 104.5 no C63 . C68 . H682 . 105.0 no C69 . C68 . H682 . 104.1 no H681 . C68 . H682 . 109.6 no C68 . C69 . H691 . 109.6 no C68 . C69 . H692 . 110.2 no H691 . C69 . H692 . 109.8 no C68 . C69 . H693 . 108.4 no H691 . C69 . H693 . 108.3 no H692 . C69 . H693 . 110.6 no C72 . C71 . C76 . 119.8(10) yes C72 . C71 . C77 . 119.8(10) yes C76 . C71 . C77 . 120.4(10) yes C71 . C72 . C73 . 119.3(9) yes C71 . C72 . H721 . 121.2 no C73 . C72 . H721 . 119.5 no C72 . C73 . C74 . 119.6(9) yes C72 . C73 . C78 . 118.4(11) yes C74 . C73 . C78 . 122.0(11) yes C73 . C74 . C75 . 120.7(10) yes C73 . C74 . H741 . 120.6 no C75 . C74 . H741 . 118.7 no C74 . C75 . C76 . 119.9(11) yes C74 . C75 . H751 . 119.7 no C76 . C75 . H751 . 120.4 no C71 . C76 . C75 . 120.7(10) yes C71 . C76 . H761 . 119.2 no C75 . C76 . H761 . 120.1 no C71 . C77 . H771 . 108.8 no C71 . C77 . H772 . 109.7 no H771 . C77 . H772 . 109.9 no C71 . C77 . H773 . 110.0 no H771 . C77 . H773 . 109.1 no H772 . C77 . H773 . 109.4 no C73 . C78 . H781 . 106.1 no C73 . C78 . H782 . 109.7 no H781 . C78 . H782 . 109.5 no C73 . C78 . H783 . 109.7 no H781 . C78 . H783 . 109.7 no H782 . C78 . H783 . 112.0 no # Attachment 'sg21.cif' data_sg21 _database_code_depnum_ccdc_archive 'CCDC 673654' _audit_creation_date 07-02-22 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '2221011 sg21_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 11.2478(2) _cell_length_b 13.9007(2) _cell_length_c 14.9298(3) _cell_angle_alpha 90.3583(11) _cell_angle_beta 110.9346(11) _cell_angle_gamma 90.1421(12) _cell_volume 2180.15(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 2 # Given Formula = C104 H80 Cl2 N8 O16 # Dc = 2.69 Fooo = 972.00 Mu = 3.01 M = 1768.73 # Found Formula = C53 H42 Cl2 N4 O8 # Dc = 1.42 FOOO = 972.00 Mu = 2.14 M = 933.84 _chemical_formula_sum 'C53 H42 Cl2 N4 O8' _chemical_formula_moiety 'C52 H40 N4 O8, 0.5(C H2 Cl2), 0.5(C H2 Cl2)' _chemical_compound_source ? _chemical_formula_weight 933.84 _cell_measurement_reflns_used 10367 _cell_measurement_theta_min 1 _cell_measurement_theta_max 28 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 0.214 # 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 0.97 _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_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 20283 _reflns_number_total 10386 _diffrn_reflns_av_R_equivalents 0.041 # Number of reflections with Friedels Law is 10386 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 10395 _diffrn_reflns_theta_min 1.967 _diffrn_reflns_theta_max 27.871 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.871 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -14 _reflns_limit_h_max 13 _reflns_limit_k_min -18 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.09 _refine_diff_density_max 0.43 _refine_ls_number_reflns 6267 _refine_ls_number_restraints 25 _refine_ls_number_parameters 622 #_refine_ls_R_factor_ref 0.0662 _refine_ls_wR_factor_ref 0.0707 _refine_ls_goodness_of_fit_ref 1.1417 #_reflns_number_all 10288 _refine_ls_R_factor_all 0.1136 _refine_ls_wR_factor_all 0.1089 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.0\s(I) _reflns_number_gt 6267 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_gt 0.0707 _refine_ls_shift/su_max 0.000203 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.967 1.12 0.546 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. 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 _atom_site_attached_hydrogens O1 O 0.5051(2) 0.23320(13) 0.44747(13) 0.0369 1.0000 Uani . . . . . . O2 O 0.19741(19) -0.15218(15) 0.58165(14) 0.0423 1.0000 Uani . . . . . . O3 O 0.5518(2) -0.20269(15) 0.84303(15) 0.0441 1.0000 Uani . . . . . . O4 O 0.84323(18) 0.20202(14) 0.72513(15) 0.0386 1.0000 Uani . . . . . . O5 O 0.1351(2) 0.09055(15) 0.97238(14) 0.0456 1.0000 Uani . . . . . . O6 O 0.3823(2) 0.49528(14) 0.81024(15) 0.0416 1.0000 Uani . . . . . . O7 O 0.2549(2) 0.36131(16) 0.51273(14) 0.0489 1.0000 Uani . . . . . . O8 O -0.04266(18) -0.01552(13) 0.66622(13) 0.0363 1.0000 Uani . . . . . . N1 N 0.6694(2) 0.22332(14) 0.59074(15) 0.0285 1.0000 Uani . . . . . . N2 N 0.3739(2) -0.17628(15) 0.71362(15) 0.0281 1.0000 Uani . . . . . . N3 N 0.06007(19) 0.03132(14) 0.82061(15) 0.0269 1.0000 Uani . . . . . . N4 N 0.3242(2) 0.42636(14) 0.66243(15) 0.0297 1.0000 Uani . . . . . . C1 C 0.8406(3) 0.6211(2) 0.7704(2) 0.0397 1.0000 Uani . . . . . . C2 C 0.8274(4) 0.6407(3) 0.8678(2) 0.0532 1.0000 Uani . . . . . . C3 C 0.8131(4) 0.7153(3) 0.7135(3) 0.0634 1.0000 Uani . . . . . . C4 C 0.9769(4) 0.5901(3) 0.7892(3) 0.0697 1.0000 Uani . . . . . . C5 C 0.7430(3) 0.54507(18) 0.71295(18) 0.0319 1.0000 Uani . . . . . . C6 C 0.7771(3) 0.46452(18) 0.67214(19) 0.0320 1.0000 Uani . . . . . . C7 C 0.6866(3) 0.39891(17) 0.61642(18) 0.0300 1.0000 Uani . . . . . . C8 C 0.5591(3) 0.41345(17) 0.60252(18) 0.0299 1.0000 Uani . . . . . . C9 C 0.5234(2) 0.49154(17) 0.64562(17) 0.0280 1.0000 Uani . . . . . . C10 C 0.6140(3) 0.55654(18) 0.69919(19) 0.0325 1.0000 Uani . . . . . . C11 C 0.7258(3) 0.31284(18) 0.5707(2) 0.0324 1.0000 Uani . . . . . . C12 C 0.5518(3) 0.19374(17) 0.52524(18) 0.0285 1.0000 Uani . . . . . . C13 C 0.4859(2) 0.11404(17) 0.55401(17) 0.0255 1.0000 Uani . . . . . . C14 C 0.3640(2) 0.08755(18) 0.49786(17) 0.0289 1.0000 Uani . . . . . . C15 C 0.3039(2) 0.00952(18) 0.52429(18) 0.0288 1.0000 Uani . . . . . . C16 C 0.3671(2) -0.04231(17) 0.60569(17) 0.0253 1.0000 Uani . . . . . . C17 C 0.3041(2) -0.12670(18) 0.63031(17) 0.0288 1.0000 Uani . . . . . . C18 C 0.4984(2) -0.15363(19) 0.77341(18) 0.0299 1.0000 Uani . . . . . . C19 C 0.5589(2) -0.06882(17) 0.74824(17) 0.0261 1.0000 Uani . . . . . . C20 C 0.6792(2) -0.04046(19) 0.80597(18) 0.0305 1.0000 Uani . . . . . . C21 C 0.7362(2) 0.04012(18) 0.78209(18) 0.0294 1.0000 Uani . . . . . . C22 C 0.6749(2) 0.09031(16) 0.69954(18) 0.0262 1.0000 Uani . . . . . . C23 C 0.7376(2) 0.17499(17) 0.67513(18) 0.0288 1.0000 Uani . . . . . . C24 C 0.5507(2) 0.06365(16) 0.63940(17) 0.0241 1.0000 Uani . . . . . . C25 C 0.4913(2) -0.01597(17) 0.66458(16) 0.0244 1.0000 Uani . . . . . . C26 C 0.3139(3) -0.25925(17) 0.74145(19) 0.0296 1.0000 Uani . . . . . . C27 C 0.2602(2) -0.23381(17) 0.81756(18) 0.0278 1.0000 Uani . . . . . . C28 C 0.2940(2) -0.28714(18) 0.90164(18) 0.0287 1.0000 Uani . . . . . . C29 C 0.2420(3) -0.26810(18) 0.97164(18) 0.0308 1.0000 Uani . . . . . . C30 C 0.1570(2) -0.19044(18) 0.95579(18) 0.0295 1.0000 Uani . . . . . . C31 C 0.1225(2) -0.13705(17) 0.87262(18) 0.0273 1.0000 Uani . . . . . . C32 C 0.1731(2) -0.15950(18) 0.80288(18) 0.0292 1.0000 Uani . . . . . . C33 C 0.2777(3) -0.3278(2) 1.0632(2) 0.0388 1.0000 Uani . . . . . . C34 C 0.3827(4) -0.2736(3) 1.1430(2) 0.0514 1.0000 Uani . . . . . . C35 C 0.3278(4) -0.4270(2) 1.0492(2) 0.0496 1.0000 Uani . . . . . . C36 C 0.1614(4) -0.3435(3) 1.0919(2) 0.0527 1.0000 Uani . . . . . . C37 C 0.0228(2) -0.05902(17) 0.85514(19) 0.0285 1.0000 Uani . . . . . . C38 C 0.1215(2) 0.10189(18) 0.88856(18) 0.0295 1.0000 Uani . . . . . . C39 C 0.1702(2) 0.18769(18) 0.85448(18) 0.0295 1.0000 Uani . . . . . . C40 C 0.2375(3) 0.25796(19) 0.91848(18) 0.0330 1.0000 Uani . . . . . . C41 C 0.2878(3) 0.33735(19) 0.88622(19) 0.0348 1.0000 Uani . . . . . . C42 C 0.2747(2) 0.34547(17) 0.79111(18) 0.0287 1.0000 Uani . . . . . . C43 C 0.3309(2) 0.42866(17) 0.75852(19) 0.0295 1.0000 Uani . . . . . . C44 C 0.2587(3) 0.3569(2) 0.59505(19) 0.0333 1.0000 Uani . . . . . . C45 C 0.1953(2) 0.27810(18) 0.62749(18) 0.0294 1.0000 Uani . . . . . . C46 C 0.1245(3) 0.21039(19) 0.56307(18) 0.0328 1.0000 Uani . . . . . . C47 C 0.0675(2) 0.13345(19) 0.59371(18) 0.0315 1.0000 Uani . . . . . . C48 C 0.0825(2) 0.12577(17) 0.68905(17) 0.0266 1.0000 Uani . . . . . . C49 C 0.0264(2) 0.04275(17) 0.72172(17) 0.0271 1.0000 Uani . . . . . . C50 C 0.1531(2) 0.19541(16) 0.75645(17) 0.0248 1.0000 Uani . . . . . . C51 C 0.2078(2) 0.27369(17) 0.72532(17) 0.0262 1.0000 Uani . . . . . . C52 C 0.3837(3) 0.50708(18) 0.6289(2) 0.0327 1.0000 Uani . . . . . . C53 C 0.5456(9) 0.0511(7) 0.9969(6) 0.0886 0.5000 Uani D U . . . . C54 C 0.9867(7) 0.4911(5) 0.5453(5) 0.0635 0.5000 Uani D U . . . . Cl1 Cl 0.5602(6) -0.0377(4) 1.0833(5) 0.1136 0.5000 Uani D U . . . . Cl2 Cl 0.4157(4) 0.0318(4) 0.8915(4) 0.0991 0.5000 Uani D U . . . . Cl3 Cl 0.93191(13) 0.41511(11) 0.45006(13) 0.1136 1.0000 Uani D U . . . . H21 H 0.8407 0.5821 0.9044 0.0782 1.0000 Uiso R . . . . . H22 H 0.8909 0.6891 0.9022 0.0780 1.0000 Uiso R . . . . . H23 H 0.7431 0.6655 0.8573 0.0783 1.0000 Uiso R . . . . . H31 H 0.8190 0.7053 0.6523 0.0871 1.0000 Uiso R . . . . . H32 H 0.8762 0.7624 0.7496 0.0869 1.0000 Uiso R . . . . . H33 H 0.7298 0.7381 0.7076 0.0871 1.0000 Uiso R . . . . . H41 H 0.9865 0.5795 0.7278 0.1011 1.0000 Uiso R . . . . . H42 H 1.0350 0.6417 0.8248 0.1010 1.0000 Uiso R . . . . . H43 H 0.9938 0.5311 0.8252 0.1011 1.0000 Uiso R . . . . . H61 H 0.8644 0.4553 0.6822 0.0351 1.0000 Uiso R . . . . . H81 H 0.4959 0.3693 0.5637 0.0351 1.0000 Uiso R . . . . . H101 H 0.5888 0.6091 0.7267 0.0369 1.0000 Uiso R . . . . . H111 H 0.8177 0.3059 0.5937 0.0421 1.0000 Uiso R . . . . . H112 H 0.6938 0.3200 0.5000 0.0420 1.0000 Uiso R . . . . . H141 H 0.3205 0.1203 0.4411 0.0301 1.0000 Uiso R . . . . . H151 H 0.2209 -0.0062 0.4862 0.0301 1.0000 Uiso R . . . . . H201 H 0.7220 -0.0766 0.8607 0.0351 1.0000 Uiso R . . . . . H211 H 0.8175 0.0617 0.8233 0.0361 1.0000 Uiso R . . . . . H261 H 0.3763 -0.3108 0.7655 0.0409 1.0000 Uiso R . . . . . H262 H 0.2442 -0.2828 0.6838 0.0410 1.0000 Uiso R . . . . . H281 H 0.3510 -0.3388 0.9100 0.0331 1.0000 Uiso R . . . . . H301 H 0.1240 -0.1730 1.0029 0.0333 1.0000 Uiso R . . . . . H321 H 0.1490 -0.1238 0.7456 0.0352 1.0000 Uiso R . . . . . H341 H 0.4064 -0.3074 1.2032 0.0711 1.0000 Uiso R . . . . . H342 H 0.3524 -0.2102 1.1521 0.0709 1.0000 Uiso R . . . . . H343 H 0.4578 -0.2645 1.1261 0.0711 1.0000 Uiso R . . . . . H351 H 0.3457 -0.4647 1.1066 0.0748 1.0000 Uiso R . . . . . H352 H 0.4033 -0.4222 1.0337 0.0750 1.0000 Uiso R . . . . . H353 H 0.2636 -0.4590 0.9976 0.0750 1.0000 Uiso R . . . . . H361 H 0.1826 -0.3879 1.1451 0.0839 1.0000 Uiso R . . . . . H362 H 0.1329 -0.2845 1.1102 0.0840 1.0000 Uiso R . . . . . H363 H 0.0931 -0.3721 1.0388 0.0840 1.0000 Uiso R . . . . . H371 H 0.0120 -0.0444 0.9167 0.0351 1.0000 Uiso R . . . . . H372 H -0.0572 -0.0819 0.8085 0.0352 1.0000 Uiso R . . . . . H401 H 0.2489 0.2529 0.9830 0.0392 1.0000 Uiso R . . . . . H411 H 0.3312 0.3841 0.9300 0.0401 1.0000 Uiso R . . . . . H461 H 0.1131 0.2135 0.4972 0.0362 1.0000 Uiso R . . . . . H471 H 0.0199 0.0879 0.5497 0.0351 1.0000 Uiso R . . . . . H521 H 0.3766 0.5662 0.6637 0.0421 1.0000 Uiso R . . . . . H522 H 0.3376 0.5152 0.5599 0.0423 1.0000 Uiso R . . . . . H531 H 0.5316 0.1142 1.0193 0.1140 0.5000 Uiso R . . . . . H532 H 0.6196 0.0534 0.9780 0.1140 0.5000 Uiso R . . . . . H541 H 1.0437 0.4577 0.6008 0.0748 0.5000 Uiso R . . . . . H542 H 0.9150 0.5159 0.5599 0.0748 0.5000 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 O1 0.0512(12) 0.0290(9) 0.0302(10) 0.0059(7) 0.0140(9) -0.0012(8) O2 0.0364(11) 0.0502(12) 0.0344(10) 0.0044(9) 0.0053(8) -0.0135(9) O3 0.0392(11) 0.0436(11) 0.0453(12) 0.0217(9) 0.0095(9) 0.0028(9) O4 0.0319(10) 0.0317(10) 0.0490(12) 0.0014(8) 0.0105(9) -0.0032(8) O5 0.0619(14) 0.0464(12) 0.0300(10) 0.0029(9) 0.0183(9) -0.0123(10) O6 0.0550(13) 0.0304(10) 0.0420(11) -0.0052(8) 0.0207(10) -0.0105(9) O7 0.0657(14) 0.0520(12) 0.0317(11) 0.0007(9) 0.0207(10) -0.0215(11) O8 0.0354(10) 0.0330(9) 0.0336(10) 0.0031(8) 0.0041(8) -0.0079(8) N1 0.0357(11) 0.0218(10) 0.0319(11) 0.0015(8) 0.0168(9) -0.0013(8) N2 0.0303(11) 0.0279(10) 0.0293(10) 0.0020(8) 0.0144(9) -0.0022(8) N3 0.0262(10) 0.0252(10) 0.0301(11) 0.0048(8) 0.0111(8) 0.0006(8) N4 0.0347(11) 0.0232(10) 0.0331(11) 0.0027(8) 0.0144(9) -0.0017(8) C1 0.0443(16) 0.0365(14) 0.0364(14) -0.0081(11) 0.0121(12) -0.0121(12) C2 0.057(2) 0.059(2) 0.0369(16) -0.0138(14) 0.0100(15) -0.0112(16) C3 0.086(3) 0.0447(18) 0.0495(19) -0.0039(15) 0.0117(18) -0.0307(18) C4 0.045(2) 0.074(3) 0.088(3) -0.038(2) 0.023(2) -0.0206(18) C5 0.0371(14) 0.0293(13) 0.0291(13) 0.0008(10) 0.0117(11) -0.0054(10) C6 0.0362(14) 0.0282(12) 0.0314(13) 0.0021(10) 0.0118(11) -0.0026(10) C7 0.0390(14) 0.0237(12) 0.0310(13) 0.0025(10) 0.0172(11) -0.0028(10) C8 0.0369(13) 0.0223(11) 0.0300(12) 0.0017(9) 0.0112(11) -0.0036(10) C9 0.0357(13) 0.0233(11) 0.0260(12) 0.0032(9) 0.0122(10) -0.0014(10) C10 0.0437(15) 0.0243(12) 0.0323(13) -0.0002(10) 0.0170(11) -0.0008(10) C11 0.0379(14) 0.0236(12) 0.0425(15) 0.0015(10) 0.0226(12) -0.0052(10) C12 0.0377(14) 0.0219(11) 0.0303(13) -0.0007(9) 0.0176(11) 0.0014(10) C13 0.0310(12) 0.0240(11) 0.0249(11) 0.0009(9) 0.0139(10) 0.0032(9) C14 0.0333(13) 0.0280(12) 0.0248(12) 0.0033(9) 0.0095(10) 0.0025(10) C15 0.0273(12) 0.0313(12) 0.0272(12) -0.0005(10) 0.0089(10) 0.0000(10) C16 0.0259(12) 0.0283(12) 0.0232(11) -0.0009(9) 0.0108(9) 0.0001(9) C17 0.0333(13) 0.0293(12) 0.0264(12) 0.0002(10) 0.0139(10) -0.0019(10) C18 0.0285(12) 0.0316(12) 0.0314(13) 0.0034(10) 0.0128(10) 0.0022(10) C19 0.0277(12) 0.0284(12) 0.0246(11) 0.0012(9) 0.0121(10) 0.0028(9) C20 0.0271(12) 0.0340(13) 0.0289(12) 0.0064(10) 0.0081(10) 0.0046(10) C21 0.0226(11) 0.0314(13) 0.0311(13) 0.0001(10) 0.0059(10) 0.0026(10) C22 0.0278(12) 0.0226(11) 0.0309(12) -0.0025(9) 0.0138(10) 0.0001(9) C23 0.0292(12) 0.0252(12) 0.0339(13) -0.0027(10) 0.0138(11) 0.0022(10) C24 0.0264(12) 0.0217(11) 0.0254(11) -0.0001(9) 0.0107(9) 0.0024(9) C25 0.0258(11) 0.0261(11) 0.0229(11) -0.0021(9) 0.0107(9) 0.0032(9) C26 0.0378(14) 0.0235(11) 0.0315(13) 0.0015(9) 0.0174(11) -0.0041(10) C27 0.0290(12) 0.0238(11) 0.0322(13) -0.0005(9) 0.0130(10) -0.0041(9) C28 0.0298(12) 0.0260(11) 0.0302(12) 0.0022(9) 0.0107(10) 0.0023(9) C29 0.0343(13) 0.0282(12) 0.0295(13) 0.0034(10) 0.0108(11) 0.0013(10) C30 0.0337(13) 0.0301(12) 0.0267(12) 0.0027(10) 0.0131(10) 0.0012(10) C31 0.0258(12) 0.0265(12) 0.0307(12) 0.0023(10) 0.0113(10) -0.0005(9) C32 0.0316(13) 0.0270(12) 0.0297(12) 0.0054(10) 0.0120(10) -0.0005(10) C33 0.0515(17) 0.0362(14) 0.0321(14) 0.0071(11) 0.0189(13) 0.0110(12) C34 0.061(2) 0.0553(19) 0.0304(15) 0.0056(13) 0.0069(14) 0.0189(16) C35 0.073(2) 0.0381(16) 0.0415(17) 0.0145(13) 0.0249(16) 0.0191(15) C36 0.063(2) 0.058(2) 0.0454(17) 0.0255(15) 0.0292(16) 0.0150(16) C37 0.0274(12) 0.0247(11) 0.0365(13) 0.0050(10) 0.0149(10) 0.0002(9) C38 0.0302(13) 0.0299(13) 0.0293(13) 0.0030(10) 0.0118(10) -0.0007(10) C39 0.0300(13) 0.0293(12) 0.0309(13) 0.0020(10) 0.0129(10) 0.0017(10) C40 0.0413(15) 0.0331(13) 0.0264(12) -0.0021(10) 0.0144(11) -0.0031(11) C41 0.0424(15) 0.0312(13) 0.0316(13) -0.0064(10) 0.0143(12) -0.0058(11) C42 0.0315(13) 0.0265(12) 0.0295(12) 0.0003(10) 0.0125(10) 0.0023(10) C43 0.0304(13) 0.0231(11) 0.0355(13) -0.0002(10) 0.0122(11) -0.0010(9) C44 0.0319(13) 0.0357(14) 0.0312(13) 0.0034(11) 0.0099(11) -0.0023(11) C45 0.0300(13) 0.0272(12) 0.0312(13) 0.0032(10) 0.0109(10) 0.0008(10) C46 0.0382(14) 0.0336(13) 0.0253(12) 0.0020(10) 0.0095(11) -0.0011(11) C47 0.0323(13) 0.0308(13) 0.0266(12) -0.0005(10) 0.0047(10) -0.0044(10) C48 0.0246(11) 0.0249(11) 0.0275(12) 0.0030(9) 0.0060(9) 0.0008(9) C49 0.0232(11) 0.0279(12) 0.0284(12) 0.0035(10) 0.0071(10) -0.0002(9) C50 0.0236(11) 0.0246(11) 0.0264(12) 0.0024(9) 0.0091(9) 0.0028(9) C51 0.0237(11) 0.0257(11) 0.0287(12) 0.0026(9) 0.0088(10) 0.0032(9) C52 0.0392(14) 0.0251(12) 0.0377(14) 0.0038(10) 0.0184(12) -0.0013(10) C53 0.083(6) 0.097(6) 0.085(6) -0.021(5) 0.029(5) -0.041(5) C54 0.058(4) 0.071(5) 0.068(4) 0.028(3) 0.029(4) 0.025(4) Cl1 0.127(5) 0.082(3) 0.159(5) 0.019(3) 0.084(4) 0.027(3) Cl2 0.0400(12) 0.133(3) 0.110(2) -0.073(2) 0.0099(13) 0.0175(14) Cl3 0.0684(8) 0.1014(10) 0.1515(14) -0.0225(9) 0.0156(8) 0.0024(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2416(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C12 . 1.224(3) yes O2 . C17 . 1.211(3) yes O3 . C18 . 1.213(3) yes O4 . C23 . 1.213(3) yes O5 . C38 . 1.217(3) yes O6 . C43 . 1.207(3) yes O7 . C44 . 1.216(3) yes O8 . C49 . 1.214(3) yes N1 . C11 . 1.476(3) yes N1 . C12 . 1.394(3) yes N1 . C23 . 1.396(3) yes N2 . C17 . 1.398(3) yes N2 . C18 . 1.399(3) yes N2 . C26 . 1.470(3) yes N3 . C37 . 1.476(3) yes N3 . C38 . 1.397(3) yes N3 . C49 . 1.397(3) yes N4 . C43 . 1.409(3) yes N4 . C44 . 1.394(3) yes N4 . C52 . 1.484(3) yes C1 . C2 . 1.535(4) yes C1 . C3 . 1.537(5) yes C1 . C4 . 1.521(5) yes C1 . C5 . 1.538(4) yes C2 . H21 . 0.967 no C2 . H22 . 0.979 no C2 . H23 . 0.969 no C3 . H31 . 0.949 no C3 . H32 . 0.971 no C3 . H33 . 0.963 no C4 . H41 . 0.970 no C4 . H42 . 0.984 no C4 . H43 . 0.965 no C5 . C6 . 1.390(4) yes C5 . C10 . 1.401(4) yes C6 . C7 . 1.393(4) yes C6 . H61 . 0.948 no C7 . C8 . 1.390(4) yes C7 . C11 . 1.516(4) yes C8 . C9 . 1.390(4) yes C8 . H81 . 0.957 no C9 . C10 . 1.378(4) yes C9 . C52 . 1.516(4) yes C10 . H101 . 0.928 no C11 . H111 . 0.971 no C11 . H112 . 0.992 no C12 . C13 . 1.480(3) yes C13 . C14 . 1.375(4) yes C13 . C24 . 1.413(3) yes C14 . C15 . 1.408(4) yes C14 . H141 . 0.935 no C15 . C16 . 1.377(3) yes C15 . H151 . 0.928 no C16 . C17 . 1.484(3) yes C16 . C25 . 1.405(3) yes C18 . C19 . 1.476(4) yes C19 . C20 . 1.374(4) yes C19 . C25 . 1.419(3) yes C20 . C21 . 1.399(4) yes C20 . H201 . 0.937 no C21 . C22 . 1.374(3) yes C21 . H211 . 0.948 no C22 . C23 . 1.483(3) yes C22 . C24 . 1.412(3) yes C24 . C25 . 1.412(3) yes C26 . C27 . 1.505(3) yes C26 . H261 . 0.980 no C26 . H262 . 0.988 no C27 . C28 . 1.394(3) yes C27 . C32 . 1.389(4) yes C28 . C29 . 1.393(4) yes C28 . H281 . 0.943 no C29 . C30 . 1.408(4) yes C29 . C33 . 1.531(4) yes C30 . C31 . 1.383(3) yes C30 . H301 . 0.936 no C31 . C32 . 1.388(4) yes C31 . C37 . 1.517(3) yes C32 . H321 . 0.945 no C33 . C34 . 1.536(5) yes C33 . C35 . 1.532(4) yes C33 . C36 . 1.531(4) yes C34 . H341 . 0.967 no C34 . H342 . 0.972 no C34 . H343 . 0.972 no C35 . H351 . 0.967 no C35 . H352 . 0.959 no C35 . H353 . 0.953 no C36 . H361 . 0.970 no C36 . H362 . 0.954 no C36 . H363 . 0.968 no C37 . H371 . 0.990 no C37 . H372 . 0.972 no C38 . C39 . 1.478(3) yes C39 . C40 . 1.381(4) yes C39 . C50 . 1.411(3) yes C40 . C41 . 1.403(4) yes C40 . H401 . 0.929 no C41 . C42 . 1.380(4) yes C41 . H411 . 0.923 no C42 . C43 . 1.482(3) yes C42 . C51 . 1.408(4) yes C44 . C45 . 1.481(4) yes C45 . C46 . 1.372(4) yes C45 . C51 . 1.418(3) yes C46 . C47 . 1.406(4) yes C46 . H461 . 0.946 no C47 . C48 . 1.377(3) yes C47 . H471 . 0.928 no C48 . C49 . 1.480(3) yes C48 . C50 . 1.412(3) yes C50 . C51 . 1.409(3) yes C52 . H521 . 0.988 no C52 . H522 . 0.981 no C53 . Cl1 . 1.755(8) yes C53 . Cl2 . 1.742(7) yes C53 . H531 . 0.970 no C53 . H532 . 0.970 no C54 . Cl3 2_766 1.578(8) yes C54 . Cl3 . 1.694(7) yes C54 . H541 . 0.970 no C54 . H542 . 0.970 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 C11 . N1 . C12 . 118.0(2) yes C11 . N1 . C23 . 117.2(2) yes C12 . N1 . C23 . 124.7(2) yes C17 . N2 . C18 . 125.0(2) yes C17 . N2 . C26 . 118.4(2) yes C18 . N2 . C26 . 116.6(2) yes C37 . N3 . C38 . 117.9(2) yes C37 . N3 . C49 . 117.9(2) yes C38 . N3 . C49 . 124.1(2) yes C43 . N4 . C44 . 124.6(2) yes C43 . N4 . C52 . 117.7(2) yes C44 . N4 . C52 . 117.5(2) yes C2 . C1 . C3 . 107.9(3) yes C2 . C1 . C4 . 107.9(3) yes C3 . C1 . C4 . 109.7(3) yes C2 . C1 . C5 . 110.8(2) yes C3 . C1 . C5 . 108.2(2) yes C4 . C1 . C5 . 112.2(3) yes C1 . C2 . H21 . 110.0 no C1 . C2 . H22 . 108.4 no H21 . C2 . H22 . 110.1 no C1 . C2 . H23 . 109.2 no H21 . C2 . H23 . 109.9 no H22 . C2 . H23 . 109.2 no C1 . C3 . H31 . 110.0 no C1 . C3 . H32 . 107.6 no H31 . C3 . H32 . 109.9 no C1 . C3 . H33 . 109.4 no H31 . C3 . H33 . 111.0 no H32 . C3 . H33 . 108.9 no C1 . C4 . H41 . 108.3 no C1 . C4 . H42 . 108.8 no H41 . C4 . H42 . 109.9 no C1 . C4 . H43 . 109.4 no H41 . C4 . H43 . 109.6 no H42 . C4 . H43 . 110.9 no C1 . C5 . C6 . 122.6(2) yes C1 . C5 . C10 . 119.8(2) yes C6 . C5 . C10 . 117.6(2) yes C5 . C6 . C7 . 121.7(3) yes C5 . C6 . H61 . 118.3 no C7 . C6 . H61 . 120.0 no C6 . C7 . C8 . 119.2(2) yes C6 . C7 . C11 . 120.8(2) yes C8 . C7 . C11 . 120.0(2) yes C7 . C8 . C9 . 120.0(2) yes C7 . C8 . H81 . 119.9 no C9 . C8 . H81 . 120.1 no C8 . C9 . C10 . 119.9(2) yes C8 . C9 . C52 . 119.4(2) yes C10 . C9 . C52 . 120.6(2) yes C5 . C10 . C9 . 121.4(2) yes C5 . C10 . H101 . 119.4 no C9 . C10 . H101 . 119.2 no C7 . C11 . N1 . 110.9(2) yes C7 . C11 . H111 . 111.5 no N1 . C11 . H111 . 108.8 no C7 . C11 . H112 . 109.9 no N1 . C11 . H112 . 106.7 no H111 . C11 . H112 . 108.9 no N1 . C12 . O1 . 120.8(2) yes N1 . C12 . C13 . 117.4(2) yes O1 . C12 . C13 . 121.8(2) yes C12 . C13 . C14 . 120.8(2) yes C12 . C13 . C24 . 119.2(2) yes C14 . C13 . C24 . 119.9(2) yes C13 . C14 . C15 . 120.3(2) yes C13 . C14 . H141 . 120.6 no C15 . C14 . H141 . 119.1 no C14 . C15 . C16 . 120.5(2) yes C14 . C15 . H151 . 118.9 no C16 . C15 . H151 . 120.6 no C15 . C16 . C17 . 119.7(2) yes C15 . C16 . C25 . 120.1(2) yes C17 . C16 . C25 . 120.1(2) yes C16 . C17 . N2 . 116.7(2) yes C16 . C17 . O2 . 122.5(2) yes N2 . C17 . O2 . 120.8(2) yes N2 . C18 . O3 . 119.9(2) yes N2 . C18 . C19 . 117.4(2) yes O3 . C18 . C19 . 122.7(2) yes C18 . C19 . C20 . 120.3(2) yes C18 . C19 . C25 . 119.5(2) yes C20 . C19 . C25 . 120.2(2) yes C19 . C20 . C21 . 120.2(2) yes C19 . C20 . H201 . 118.6 no C21 . C20 . H201 . 121.2 no C20 . C21 . C22 . 120.8(2) yes C20 . C21 . H211 . 120.4 no C22 . C21 . H211 . 118.8 no C21 . C22 . C23 . 120.0(2) yes C21 . C22 . C24 . 120.2(2) yes C23 . C22 . C24 . 119.8(2) yes C22 . C23 . N1 . 117.0(2) yes C22 . C23 . O4 . 122.5(2) yes N1 . C23 . O4 . 120.6(2) yes C13 . C24 . C22 . 121.3(2) yes C13 . C24 . C25 . 119.6(2) yes C22 . C24 . C25 . 119.1(2) yes C19 . C25 . C24 . 119.3(2) yes C19 . C25 . C16 . 121.2(2) yes C24 . C25 . C16 . 119.5(2) yes N2 . C26 . C27 . 112.4(2) yes N2 . C26 . H261 . 109.8 no C27 . C26 . H261 . 108.8 no N2 . C26 . H262 . 108.0 no C27 . C26 . H262 . 109.0 no H261 . C26 . H262 . 108.8 no C26 . C27 . C28 . 120.1(2) yes C26 . C27 . C32 . 120.3(2) yes C28 . C27 . C32 . 119.6(2) yes C27 . C28 . C29 . 121.5(2) yes C27 . C28 . H281 . 119.0 no C29 . C28 . H281 . 119.5 no C28 . C29 . C30 . 117.4(2) yes C28 . C29 . C33 . 121.4(2) yes C30 . C29 . C33 . 121.2(2) yes C29 . C30 . C31 . 121.6(2) yes C29 . C30 . H301 . 119.9 no C31 . C30 . H301 . 118.5 no C30 . C31 . C32 . 119.7(2) yes C30 . C31 . C37 . 119.8(2) yes C32 . C31 . C37 . 120.4(2) yes C27 . C32 . C31 . 120.1(2) yes C27 . C32 . H321 . 119.9 no C31 . C32 . H321 . 120.0 no C29 . C33 . C34 . 108.1(2) yes C29 . C33 . C35 . 111.3(2) yes C34 . C33 . C35 . 108.9(3) yes C29 . C33 . C36 . 110.5(2) yes C34 . C33 . C36 . 110.4(3) yes C35 . C33 . C36 . 107.7(3) yes C33 . C34 . H341 . 111.3 no C33 . C34 . H342 . 109.7 no H341 . C34 . H342 . 108.1 no C33 . C34 . H343 . 111.0 no H341 . C34 . H343 . 109.1 no H342 . C34 . H343 . 107.4 no C33 . C35 . H351 . 110.1 no C33 . C35 . H352 . 111.8 no H351 . C35 . H352 . 109.2 no C33 . C35 . H353 . 108.3 no H351 . C35 . H353 . 108.8 no H352 . C35 . H353 . 108.5 no C33 . C36 . H361 . 109.6 no C33 . C36 . H362 . 111.5 no H361 . C36 . H362 . 109.1 no C33 . C36 . H363 . 109.5 no H361 . C36 . H363 . 107.6 no H362 . C36 . H363 . 109.4 no C31 . C37 . N3 . 112.79(19) yes C31 . C37 . H371 . 108.2 no N3 . C37 . H371 . 107.4 no C31 . C37 . H372 . 109.4 no N3 . C37 . H372 . 109.2 no H371 . C37 . H372 . 109.8 no N3 . C38 . O5 . 120.0(2) yes N3 . C38 . C39 . 117.4(2) yes O5 . C38 . C39 . 122.6(2) yes C38 . C39 . C40 . 120.5(2) yes C38 . C39 . C50 . 119.6(2) yes C40 . C39 . C50 . 119.8(2) yes C39 . C40 . C41 . 120.2(2) yes C39 . C40 . H401 . 119.9 no C41 . C40 . H401 . 119.9 no C40 . C41 . C42 . 121.0(2) yes C40 . C41 . H411 . 118.9 no C42 . C41 . H411 . 120.1 no C41 . C42 . C43 . 120.4(2) yes C41 . C42 . C51 . 119.3(2) yes C43 . C42 . C51 . 120.3(2) yes C42 . C43 . N4 . 116.6(2) yes C42 . C43 . O6 . 123.2(2) yes N4 . C43 . O6 . 120.2(2) yes N4 . C44 . O7 . 120.6(2) yes N4 . C44 . C45 . 117.7(2) yes O7 . C44 . C45 . 121.7(2) yes C44 . C45 . C46 . 120.1(2) yes C44 . C45 . C51 . 119.4(2) yes C46 . C45 . C51 . 120.5(2) yes C45 . C46 . C47 . 120.5(2) yes C45 . C46 . H461 . 121.5 no C47 . C46 . H461 . 118.0 no C46 . C47 . C48 . 119.9(2) yes C46 . C47 . H471 . 119.9 no C48 . C47 . H471 . 120.1 no C47 . C48 . C49 . 119.8(2) yes C47 . C48 . C50 . 120.6(2) yes C49 . C48 . C50 . 119.6(2) yes C48 . C49 . N3 . 117.1(2) yes C48 . C49 . O8 . 122.4(2) yes N3 . C49 . O8 . 120.5(2) yes C48 . C50 . C39 . 121.1(2) yes C48 . C50 . C51 . 119.4(2) yes C39 . C50 . C51 . 119.5(2) yes C45 . C51 . C50 . 118.9(2) yes C45 . C51 . C42 . 121.0(2) yes C50 . C51 . C42 . 120.0(2) yes C9 . C52 . N4 . 113.5(2) yes C9 . C52 . H521 . 107.9 no N4 . C52 . H521 . 108.6 no C9 . C52 . H522 . 108.6 no N4 . C52 . H522 . 108.3 no H521 . C52 . H522 . 109.8 no Cl1 . C53 . Cl2 . 112.8(5) yes Cl1 . C53 . H531 . 111.7 no Cl2 . C53 . H531 . 104.8 no Cl1 . C53 . H532 . 111.8 no Cl2 . C53 . H532 . 105.8 no H531 . C53 . H532 . 109.5 no Cl3 2_766 C54 . Cl3 . 125.2(4) yes Cl3 2_766 C54 . H541 . 99.6 no Cl3 . C54 . H541 . 110.4 no Cl3 2_766 C54 . H542 . 102.3 no Cl3 . C54 . H542 . 109.0 no H541 . C54 . H542 . 109.2 no