# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Arnold, Lena' _publ_contact_author_email arnold@mpip-mainz.mpg.de _publ_section_title ; A Porphyrin-Related Macrocycle from Carbazole and Pyridine Building Blocks: Synthesis and Metal Coordination ; _publ_contact_author_address ; Max-Planck-Institute for Polymer Research Ackermannweg 10 D-55021 Mainz Germany ; _publ_contact_author_fax '+49 379100' _publ_contact_author_phone '+49 379133' _publ_author_name L.Arnold # Attachment '- arnco.cif' data_arnco _database_code_depnum_ccdc_archive 'CCDC 787489' #TrackingRef '- arnco.cif' _audit_creation_date 10-10-05 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.1483(4) _cell_length_b 21.8882(9) _cell_length_c 29.7527(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5957.7(4) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 2 21 21 ' 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' 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' 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' Co 0.3494 0.9721 12.2841 4.2791 7.3409 0.2784 4.0034 13.5359 2.3488 71.1692 1.0118 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C68 H88 Co1 N4 O5.50 # Dc = 1.24 Fooo = 2060.00 Mu = 3.43 M = 1108.40 # Found Formula = C60 H72 Co1 N4 O3.50 # Dc = 1.07 FOOO = 2060.00 Mu = 3.31 M = 964.19 _chemical_formula_sum 'C68 H88 Co1 N4 O5.50' _chemical_formula_moiety 'C68 H88 Co1 N4 O5.50' _chemical_compound_source ? _chemical_formula_weight 1108.40 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_max 0.43 _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2060 _exptl_absorpt_coefficient_mu 0.331 # Sheldrick geometric approximatio 0.91 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.58 _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_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 'CRYSTALS (Betteridge et al., 2003)' _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 120 _diffrn_reflns_number 29056 _reflns_number_total 10964 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections with Friedels Law is 10964 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6817 _diffrn_reflns_theta_min 2.508 _diffrn_reflns_theta_max 27.462 _diffrn_measured_fraction_theta_max 0.872 _diffrn_reflns_theta_full 25.265 _diffrn_measured_fraction_theta_full 0.976 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 38 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 27 _reflns_limit_l_min 0 _reflns_limit_l_max 38 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.62 _refine_diff_density_max 0.55 _refine_ls_number_reflns 9174 _refine_ls_number_restraints 0 _refine_ls_number_parameters 619 #_refine_ls_R_factor_ref 0.0625 _refine_ls_wR_factor_ref 0.0630 _refine_ls_goodness_of_fit_ref 0.9431 #_reflns_number_all 10964 _refine_ls_R_factor_all 0.0826 _refine_ls_wR_factor_all 0.2536 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 9174 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_gt 0.0630 _refine_ls_shift/su_max 0.018609 _refine_ls_abs_structure_Flack 0.086(5) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # 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 ad _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: 2.33 1.98 1.09 ; # 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. Blessing, SORTAV ( ) Flack, H. D. (1983). Acta Cryst. A39, 876-881. 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 Co1 Co 0.33926(4) 0.194678(18) 0.346509(12) 0.0430 1.0000 Uani . . . . . . N1 N 0.5520(2) 0.25257(9) 0.34593(8) 0.0325 1.0000 Uani . . . . . . N2 N 0.3397(2) 0.19142(8) 0.28101(6) 0.0291 1.0000 Uani . . . . . . N3 N 0.1333(2) 0.13058(9) 0.34776(7) 0.0311 1.0000 Uani . . . . . . N4 N 0.3276(2) 0.20240(9) 0.41117(6) 0.0317 1.0000 Uani . . . . . . C1 C 0.6239(3) 0.25839(11) 0.38526(8) 0.0357 1.0000 Uani . . . . . . C5 C 0.6311(3) 0.25038(10) 0.30730(8) 0.0318 1.0000 Uani . . . . . . C6 C 0.5564(3) 0.25610(11) 0.26404(8) 0.0318 1.0000 Uani . . . . . . C8 C 0.5582(3) 0.29839(13) 0.18657(8) 0.0419 1.0000 Uani . . . . . . C10 C 0.3603(3) 0.23341(11) 0.20975(8) 0.0354 1.0000 Uani . . . . . . C11 C 0.4214(3) 0.22694(11) 0.25381(8) 0.0323 1.0000 Uani . . . . . . C12 C 0.2317(3) 0.19496(12) 0.21082(7) 0.0340 1.0000 Uani . . . . . . C13 C 0.2275(3) 0.17058(11) 0.25469(8) 0.0316 1.0000 Uani . . . . . . C14 C 0.1138(3) 0.12751(11) 0.26614(8) 0.0332 1.0000 Uani . . . . . . C16 C 0.0112(3) 0.13940(12) 0.18996(8) 0.0386 1.0000 Uani . . . . . . C18 C 0.1085(2) 0.09807(11) 0.31049(7) 0.0275 1.0000 Uani . . . . . . C22 C 0.1028(3) 0.10542(11) 0.38759(8) 0.0325 1.0000 Uani . . . . . . C23 C 0.1008(3) 0.14266(11) 0.42837(8) 0.0333 1.0000 Uani . . . . . . C25 C -0.0122(3) 0.16637(11) 0.50225(8) 0.0341 1.0000 Uani . . . . . . C27 C 0.2047(3) 0.21903(12) 0.47922(8) 0.0347 1.0000 Uani . . . . . . C28 C 0.2096(3) 0.18734(12) 0.43768(8) 0.0342 1.0000 Uani . . . . . . C29 C 0.4052(3) 0.24533(11) 0.43712(8) 0.0349 1.0000 Uani . . . . . . C30 C 0.3383(3) 0.25658(12) 0.47861(8) 0.0374 1.0000 Uani . . . . . . C32 C 0.5316(3) 0.32687(12) 0.49981(9) 0.0429 1.0000 Uani . . . . . . C34 C 0.5398(3) 0.27190(12) 0.42676(8) 0.0345 1.0000 Uani . . . . . . C35 C 0.6302(4) 0.34156(18) 0.15201(11) 0.0643 1.0000 Uani . . . . . . C39 C -0.1082(3) 0.12329(13) 0.15701(9) 0.0448 1.0000 Uani . . . . . . C43 C -0.1382(3) 0.15363(12) 0.53473(8) 0.0401 1.0000 Uani . . . . . . C47 C 0.5911(4) 0.37350(14) 0.53376(11) 0.0503 1.0000 Uani . . . . . . O2 O 0.4745(2) 0.11053(9) 0.35118(6) 0.0437 1.0000 Uani . . . . . . O61 O 0.1284(10) 0.3657(4) 0.4046(3) 0.2042 1.0000 Uani . . . . . . O65 O 0.1804(4) 0.0000 0.5000 0.0576 1.0000 Uani S T . . . . C2 C 0.7776(3) 0.25266(12) 0.38830(9) 0.0371 1.0000 Uani . . . . . . C3 C 0.8565(3) 0.24334(12) 0.34921(10) 0.0403 1.0000 Uani . . . . . . C4 C 0.7844(3) 0.24252(12) 0.30872(9) 0.0382 1.0000 Uani . . . . . . C7 C 0.6181(3) 0.29106(12) 0.22999(8) 0.0391 1.0000 Uani . . . . . . C9 C 0.4291(3) 0.26707(12) 0.17674(8) 0.0391 1.0000 Uani . . . . . . C15 C 0.0156(3) 0.11489(12) 0.23320(8) 0.0364 1.0000 Uani . . . . . . C17 C 0.1250(3) 0.18048(11) 0.17862(8) 0.0363 1.0000 Uani . . . . . . C19 C 0.0666(3) 0.03545(11) 0.31224(8) 0.0337 1.0000 Uani . . . . . . C20 C 0.0501(3) 0.00848(11) 0.35375(9) 0.0400 1.0000 Uani . . . . . . C21 C 0.0621(3) 0.04275(11) 0.39106(8) 0.0348 1.0000 Uani . . . . . . C24 C -0.0052(3) 0.13492(12) 0.46084(8) 0.0351 1.0000 Uani . . . . . . C26 C 0.0967(3) 0.20946(11) 0.51081(8) 0.0355 1.0000 Uani . . . . . . C31 C 0.3970(3) 0.29698(12) 0.50991(8) 0.0398 1.0000 Uani . . . . . . C33 C 0.5953(3) 0.31252(12) 0.45838(9) 0.0414 1.0000 Uani . . . . . . H21 H 0.8238 0.2563 0.4168 0.0486 1.0000 Uiso R . . . . . H31 H 0.9589 0.2365 0.3508 0.0542 1.0000 Uiso R . . . . . H41 H 0.8362 0.2374 0.2813 0.0564 1.0000 Uiso R . . . . . H71 H 0.7082 0.3110 0.2360 0.0481 1.0000 Uiso R . . . . . H91 H 0.3867 0.2699 0.1477 0.0548 1.0000 Uiso R . . . . . H151 H -0.0586 0.0862 0.2404 0.0494 1.0000 Uiso R . . . . . H171 H 0.1294 0.1982 0.1495 0.0457 1.0000 Uiso R . . . . . H191 H 0.0545 0.0127 0.2853 0.0426 1.0000 Uiso R . . . . . H201 H 0.0287 -0.0339 0.3557 0.0487 1.0000 Uiso R . . . . . H211 H 0.0439 0.0256 0.4199 0.0393 1.0000 Uiso R . . . . . H241 H -0.0807 0.1065 0.4542 0.0394 1.0000 Uiso R . . . . . H261 H 0.0946 0.2321 0.5380 0.0466 1.0000 Uiso R . . . . . H311 H 0.3482 0.3053 0.5374 0.0478 1.0000 Uiso R . . . . . H331 H 0.6846 0.3327 0.4517 0.0511 1.0000 Uiso R . . . . . O1 O 0.2069(4) 0.28213(19) 0.34100(19) 0.1362 1.0000 Uani . . . . . . H1 H 0.1787 0.3071 0.3635 0.1770 1.0000 Uiso R . . . . . H2 H 0.2200 0.3164 0.3219 0.1770 1.0000 Uiso R . . . . . C36 C 0.5664(10) 0.4022(3) 0.1558(3) 0.2072 1.0000 Uani . . . . . . H361 H 0.6105 0.4291 0.1347 0.2027 1.0000 Uiso R . . . . . H362 H 0.5681 0.4204 0.1847 0.2027 1.0000 Uiso R . . . . . H363 H 0.4680 0.3946 0.1472 0.2027 1.0000 Uiso R . . . . . C37 C 0.7857(7) 0.3452(3) 0.1555(2) 0.1247 1.0000 Uani . . . . . . H371 H 0.8243 0.3729 0.1340 0.1386 1.0000 Uiso R . . . . . H372 H 0.8074 0.3595 0.1849 0.1386 1.0000 Uiso R . . . . . H373 H 0.8283 0.3061 0.1513 0.1386 1.0000 Uiso R . . . . . C38 C 0.6259(6) 0.3074(3) 0.10443(13) 0.1083 1.0000 Uani . . . . . . H381 H 0.6679 0.3327 0.0819 0.1246 1.0000 Uiso R . . . . . H382 H 0.6806 0.2707 0.1069 0.1246 1.0000 Uiso R . . . . . H383 H 0.5278 0.2980 0.0965 0.1246 1.0000 Uiso R . . . . . C40 C -0.0956(4) 0.15259(17) 0.11136(10) 0.0583 1.0000 Uani . . . . . . H401 H -0.1711 0.1400 0.0915 0.0810 1.0000 Uiso R . . . . . H402 H -0.1037 0.1952 0.1167 0.0810 1.0000 Uiso R . . . . . H403 H -0.0032 0.1439 0.0983 0.0810 1.0000 Uiso R . . . . . C41 C -0.1035(6) 0.05255(15) 0.14767(15) 0.0864 1.0000 Uani . . . . . . H411 H -0.1773 0.0419 0.1266 0.1017 1.0000 Uiso R . . . . . H412 H -0.1215 0.0322 0.1753 0.1017 1.0000 Uiso R . . . . . H413 H -0.0107 0.0406 0.1363 0.1017 1.0000 Uiso R . . . . . C42 C -0.2572(5) 0.13875(19) 0.17601(12) 0.0664 1.0000 Uani . . . . . . H421 H -0.3330 0.1281 0.1556 0.0866 1.0000 Uiso R . . . . . H422 H -0.2574 0.1817 0.1806 0.0866 1.0000 Uiso R . . . . . H423 H -0.2729 0.1186 0.2039 0.0866 1.0000 Uiso R . . . . . C44 C -0.2862(4) 0.16607(15) 0.51189(10) 0.0512 1.0000 Uani . . . . . . H441 H -0.3635 0.1579 0.5324 0.0578 1.0000 Uiso R . . . . . H442 H -0.2890 0.2079 0.5033 0.0578 1.0000 Uiso R . . . . . H443 H -0.2972 0.1411 0.4860 0.0578 1.0000 Uiso R . . . . . C45 C -0.1280(4) 0.08552(15) 0.54955(11) 0.0574 1.0000 Uani . . . . . . H451 H -0.2055 0.0762 0.5696 0.0747 1.0000 Uiso R . . . . . H452 H -0.0370 0.0796 0.5643 0.0747 1.0000 Uiso R . . . . . H453 H -0.1335 0.0595 0.5241 0.0747 1.0000 Uiso R . . . . . C46 C -0.1302(4) 0.19238(16) 0.57686(9) 0.0525 1.0000 Uani . . . . . . H461 H -0.2096 0.1840 0.5965 0.0702 1.0000 Uiso R . . . . . H462 H -0.0408 0.1831 0.5916 0.0702 1.0000 Uiso R . . . . . H463 H -0.1313 0.2344 0.5688 0.0702 1.0000 Uiso R . . . . . C48 C 0.7343(7) 0.3944(3) 0.5203(2) 0.1259 1.0000 Uani . . . . . . H481 H 0.7703 0.4237 0.5411 0.1472 1.0000 Uiso R . . . . . H482 H 0.8006 0.3611 0.5184 0.1472 1.0000 Uiso R . . . . . H483 H 0.7246 0.4129 0.4916 0.1472 1.0000 Uiso R . . . . . C49 C 0.4838(6) 0.4265(2) 0.5393(2) 0.0984 1.0000 Uani . . . . . . H491 H 0.5210 0.4555 0.5601 0.1291 1.0000 Uiso R . . . . . H492 H 0.3935 0.4108 0.5501 0.1291 1.0000 Uiso R . . . . . H493 H 0.4690 0.4456 0.5110 0.1291 1.0000 Uiso R . . . . . C50 C 0.6032(6) 0.34444(19) 0.58053(13) 0.0750 1.0000 Uani . . . . . . H501 H 0.6397 0.3740 0.6010 0.0923 1.0000 Uiso R . . . . . H502 H 0.5100 0.3307 0.5904 0.0923 1.0000 Uiso R . . . . . H503 H 0.6687 0.3108 0.5792 0.0923 1.0000 Uiso R . . . . . C51 C 0.5412(6) 0.08139(19) 0.31356(12) 0.0758 1.0000 Uani . . . . . . H511 H 0.5476 0.1093 0.2892 0.0974 1.0000 Uiso R . . . . . H512 H 0.4852 0.0469 0.3047 0.0974 1.0000 Uiso R . . . . . C52 C 0.6799(6) 0.0602(3) 0.3291(2) 0.1141 1.0000 Uani . . . . . . H521 H 0.7509 0.0908 0.3230 0.1465 1.0000 Uiso R . . . . . H522 H 0.7087 0.0229 0.3153 0.1465 1.0000 Uiso R . . . . . C53 C 0.6639(6) 0.0523(3) 0.3778(2) 0.1195 1.0000 Uani . . . . . . H531 H 0.7460 0.0668 0.3941 0.1386 1.0000 Uiso R . . . . . H532 H 0.6476 0.0105 0.3848 0.1386 1.0000 Uiso R . . . . . C54 C 0.5373(6) 0.0901(2) 0.39002(12) 0.0836 1.0000 Uani . . . . . . H541 H 0.5641 0.1238 0.4084 0.1025 1.0000 Uiso R . . . . . H542 H 0.4682 0.0655 0.4055 0.1025 1.0000 Uiso R . . . . . C61 C 0.2589(10) 0.4109(4) 0.4167(3) 0.1402 1.0000 Uani . . . . . . H611 H 0.3418 0.3894 0.4276 0.1705 1.0000 Uiso R . . . . . H612 H 0.2859 0.4342 0.3911 0.1705 1.0000 Uiso R . . . . . C62 C 0.1975(10) 0.4496(4) 0.4508(3) 0.1475 1.0000 Uani . . . . . . H621 H 0.2724 0.4609 0.4713 0.1782 1.0000 Uiso R . . . . . H622 H 0.1582 0.4852 0.4371 0.1782 1.0000 Uiso R . . . . . C63 C 0.0894(12) 0.4204(5) 0.4747(3) 0.1660 1.0000 Uani . . . . . . H631 H 0.1254 0.4047 0.5024 0.1820 1.0000 Uiso R . . . . . H632 H 0.0105 0.4475 0.4805 0.1820 1.0000 Uiso R . . . . . C64 C 0.0385(11) 0.3664(5) 0.4415(4) 0.1538 1.0000 Uani . . . . . . H641 H 0.0446 0.3286 0.4571 0.1818 1.0000 Uiso R . . . . . H642 H -0.0595 0.3731 0.4322 0.1818 1.0000 Uiso R . . . . . C65 C 0.2735(4) 0.04625(18) 0.51824(16) 0.0724 1.0000 Uani . . . . . . H651 H 0.2473 0.0534 0.5487 0.0910 1.0000 Uiso R . . . . . H652 H 0.2575 0.0823 0.5012 0.0910 1.0000 Uiso R . . . . . C66 C 0.4259(7) 0.0301(3) 0.5115(3) 0.1362 1.0000 Uani . . . . . . H661 H 0.4642 0.0229 0.5407 0.1776 1.0000 Uiso R . . . . . H662 H 0.4803 0.0616 0.4973 0.1776 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 Co1 0.0477(2) 0.0484(2) 0.03294(16) 0.00129(16) 0.00096(16) -0.00363(17) N1 0.0371(11) 0.0222(9) 0.0381(10) 0.0078(9) -0.0003(9) -0.0024(8) N2 0.0349(10) 0.0237(9) 0.0289(9) 0.0057(7) -0.0005(8) 0.0075(9) N3 0.0393(11) 0.0261(9) 0.0280(9) 0.0045(8) -0.0043(9) -0.0067(8) N4 0.0409(12) 0.0283(9) 0.0259(8) 0.0020(8) 0.0020(8) 0.0049(9) C1 0.0469(16) 0.0268(12) 0.0335(12) 0.0070(10) 0.0027(11) -0.0003(10) C5 0.0400(14) 0.0218(10) 0.0336(11) 0.0066(9) 0.0017(10) -0.0080(9) C6 0.0341(13) 0.0281(11) 0.0331(11) 0.0041(9) 0.0012(10) 0.0049(10) C8 0.0547(17) 0.0417(14) 0.0293(11) 0.0026(11) 0.0043(11) -0.0080(13) C10 0.0444(15) 0.0349(13) 0.0267(10) 0.0050(9) 0.0002(10) -0.0016(11) C11 0.0365(13) 0.0305(12) 0.0298(11) 0.0062(9) 0.0012(10) 0.0048(10) C12 0.0421(14) 0.0332(12) 0.0266(10) 0.0043(10) -0.0017(9) 0.0019(11) C13 0.0375(13) 0.0295(11) 0.0279(10) 0.0052(9) -0.0001(9) 0.0027(10) C14 0.0432(15) 0.0290(12) 0.0275(11) 0.0011(9) 0.0028(10) 0.0016(10) C16 0.0471(16) 0.0378(13) 0.0308(12) -0.0016(10) -0.0025(11) -0.0010(11) C18 0.0228(11) 0.0364(12) 0.0233(10) 0.0036(9) 0.0030(8) 0.0002(9) C22 0.0455(15) 0.0269(12) 0.0251(10) 0.0012(9) 0.0010(9) 0.0009(10) C23 0.0423(14) 0.0309(12) 0.0268(11) -0.0029(9) 0.0031(10) 0.0011(10) C25 0.0487(15) 0.0298(12) 0.0238(10) 0.0044(9) 0.0038(10) 0.0024(11) C27 0.0466(15) 0.0305(12) 0.0270(10) -0.0001(9) 0.0029(10) -0.0018(10) C28 0.0442(14) 0.0314(12) 0.0269(10) -0.0015(10) 0.0040(9) 0.0010(11) C29 0.0446(15) 0.0306(12) 0.0294(11) 0.0010(10) -0.0015(10) 0.0017(11) C30 0.0526(16) 0.0312(12) 0.0284(10) -0.0002(9) 0.0019(11) -0.0022(12) C32 0.0593(18) 0.0313(13) 0.0380(13) 0.0006(11) -0.0072(12) -0.0041(12) C34 0.0427(15) 0.0313(12) 0.0294(11) 0.0055(10) -0.0052(10) -0.0007(10) C35 0.077(2) 0.079(2) 0.0375(14) 0.0218(16) 0.0073(16) -0.0245(19) C39 0.0556(17) 0.0436(15) 0.0352(13) 0.0079(12) -0.0064(12) -0.0048(12) C43 0.0628(18) 0.0304(13) 0.0271(10) 0.0018(10) 0.0030(11) -0.0032(12) C47 0.0563(19) 0.0424(16) 0.0521(17) -0.0035(13) -0.0114(14) 0.0013(13) O2 0.0549(12) 0.0404(10) 0.0358(9) 0.0017(8) -0.0053(9) 0.0148(8) O61 0.201(7) 0.226(7) 0.186(6) -0.035(6) 0.036(6) -0.014(7) O65 0.0579(19) 0.0550(18) 0.0598(18) -0.0152(15) 0.0000 0.0000 C2 0.0431(15) 0.0323(13) 0.0357(12) 0.0080(10) -0.0039(11) -0.0055(11) C3 0.0385(14) 0.0358(13) 0.0464(13) 0.0065(12) 0.0009(12) -0.0034(11) C4 0.0424(15) 0.0344(13) 0.0378(12) 0.0016(11) 0.0052(11) -0.0059(11) C7 0.0449(16) 0.0410(14) 0.0314(11) 0.0014(11) 0.0035(10) -0.0017(11) C9 0.0530(17) 0.0382(13) 0.0262(11) 0.0033(10) 0.0018(11) -0.0064(12) C15 0.0434(15) 0.0352(13) 0.0305(11) -0.0010(10) 0.0026(10) -0.0005(11) C17 0.0478(16) 0.0334(13) 0.0276(11) 0.0011(9) -0.0028(10) -0.0025(10) C19 0.0385(14) 0.0296(12) 0.0331(11) -0.0069(10) 0.0025(10) 0.0013(10) C20 0.0567(16) 0.0226(11) 0.0406(14) 0.0023(10) 0.0041(12) -0.0007(10) C21 0.0472(16) 0.0264(12) 0.0310(11) 0.0064(9) 0.0055(10) 0.0001(10) C24 0.0483(16) 0.0318(12) 0.0253(10) 0.0001(9) 0.0044(10) 0.0009(10) C26 0.0516(15) 0.0307(12) 0.0242(10) 0.0012(9) 0.0025(10) 0.0052(11) C31 0.0553(16) 0.0316(13) 0.0325(11) -0.0013(10) -0.0031(11) 0.0002(11) C33 0.0544(16) 0.0336(13) 0.0363(12) 0.0068(11) -0.0094(11) -0.0035(12) O1 0.091(3) 0.094(3) 0.223(5) -0.015(3) -0.007(3) 0.030(2) C36 0.240(9) 0.087(4) 0.295(10) 0.121(6) 0.214(9) 0.102(5) C37 0.127(5) 0.106(4) 0.141(5) 0.047(4) 0.073(4) -0.030(3) C38 0.117(4) 0.160(5) 0.048(2) 0.018(3) 0.003(2) -0.071(4) C40 0.075(2) 0.068(2) 0.0323(13) 0.0181(14) -0.0115(14) -0.0117(17) C41 0.147(4) 0.0384(17) 0.073(2) -0.0002(17) -0.055(3) -0.021(2) C42 0.072(2) 0.078(2) 0.0499(18) 0.0189(18) -0.0161(17) -0.017(2) C44 0.072(2) 0.0461(16) 0.0357(13) 0.0042(12) 0.0079(13) 0.0020(15) C45 0.072(2) 0.0467(17) 0.0539(17) 0.0232(14) 0.0143(16) 0.0005(15) C46 0.063(2) 0.0580(18) 0.0361(13) -0.0121(14) 0.0136(13) -0.0026(16) C48 0.120(4) 0.154(5) 0.104(4) -0.083(4) 0.026(3) -0.060(4) C49 0.115(4) 0.055(2) 0.126(4) -0.043(3) -0.037(3) 0.003(2) C50 0.105(3) 0.060(2) 0.060(2) -0.0055(18) -0.001(2) -0.011(2) C51 0.121(4) 0.062(2) 0.0445(17) -0.0065(16) 0.004(2) 0.041(2) C52 0.079(3) 0.116(4) 0.147(5) 0.027(4) 0.041(3) 0.045(3) C53 0.088(4) 0.129(5) 0.141(5) 0.019(4) -0.055(4) 0.048(3) C54 0.136(4) 0.073(3) 0.0414(17) 0.0145(18) -0.018(2) 0.041(3) C61 0.164(7) 0.129(6) 0.128(6) 0.027(5) 0.037(5) 0.054(6) C62 0.144(7) 0.137(6) 0.161(7) 0.029(5) 0.042(6) 0.049(5) C63 0.176(9) 0.149(7) 0.173(8) 0.047(7) 0.052(7) 0.022(7) C64 0.146(7) 0.140(7) 0.175(8) 0.050(7) 0.011(7) 0.035(6) C65 0.061(2) 0.061(2) 0.096(3) -0.037(2) -0.017(2) 0.0055(18) C66 0.100(4) 0.115(5) 0.194(7) -0.084(5) 0.004(4) -0.044(4) _refine_ls_extinction_method None 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 Co1 . N1 . 2.322(2) yes Co1 . N2 . 1.9502(19) yes Co1 . N3 . 2.3497(19) yes Co1 . N4 . 1.9343(19) yes Co1 . O2 . 2.2230(18) yes Co1 . O1 . 2.271(4) yes N1 . C1 . 1.348(3) yes N1 . C5 . 1.359(3) yes N2 . C11 . 1.349(3) yes N2 . C13 . 1.369(3) yes N3 . C18 . 1.337(3) yes N3 . C22 . 1.336(3) yes N4 . C28 . 1.376(3) yes N4 . C29 . 1.408(3) yes C1 . C34 . 1.484(4) yes C1 . C2 . 1.415(4) yes C5 . C6 . 1.463(3) yes C5 . C4 . 1.414(4) yes C6 . C11 . 1.422(4) yes C6 . C7 . 1.390(4) yes C8 . C35 . 1.544(4) yes C8 . C7 . 1.412(4) yes C8 . C9 . 1.396(4) yes C10 . C11 . 1.432(3) yes C10 . C12 . 1.447(4) yes C10 . C9 . 1.379(3) yes C12 . C13 . 1.411(3) yes C12 . C17 . 1.404(3) yes C13 . C14 . 1.444(4) yes C14 . C18 . 1.469(3) yes C14 . C15 . 1.358(4) yes C16 . C39 . 1.510(4) yes C16 . C15 . 1.394(3) yes C16 . C17 . 1.416(4) yes C18 . C19 . 1.424(3) yes C22 . C23 . 1.462(3) yes C22 . C21 . 1.425(3) yes C23 . C28 . 1.423(4) yes C23 . C24 . 1.379(4) yes C25 . C43 . 1.530(4) yes C25 . C24 . 1.413(3) yes C25 . C26 . 1.395(4) yes C27 . C28 . 1.418(3) yes C27 . C30 . 1.473(4) yes C27 . C26 . 1.380(4) yes C29 . C30 . 1.400(3) yes C29 . C34 . 1.396(4) yes C30 . C31 . 1.392(4) yes C32 . C47 . 1.536(4) yes C32 . C31 . 1.426(4) yes C32 . C33 . 1.399(4) yes C34 . C33 . 1.391(4) yes C35 . C36 . 1.455(6) yes C35 . C37 . 1.429(8) yes C35 . C38 . 1.601(6) yes C39 . C40 . 1.506(4) yes C39 . C41 . 1.574(4) yes C39 . C42 . 1.514(5) yes C43 . C44 . 1.539(5) yes C43 . C45 . 1.557(4) yes C43 . C46 . 1.516(4) yes C47 . C48 . 1.445(6) yes C47 . C49 . 1.528(6) yes C47 . C50 . 1.534(5) yes O2 . C51 . 1.425(4) yes O2 . C54 . 1.366(4) yes O61 . C61 . 1.591(11) yes O61 . C64 . 1.370(10) yes O65 . C65 2_556 1.430(4) yes O65 . C65 . 1.430(4) yes C2 . C3 . 1.384(4) yes C2 . H21 . 0.950 no C3 . C4 . 1.373(4) yes C3 . H31 . 0.950 no C4 . H41 . 0.950 no C7 . H71 . 0.950 no C9 . H91 . 0.950 no C15 . H151 . 0.950 no C17 . H171 . 0.950 no C19 . C20 . 1.377(4) yes C19 . H191 . 0.950 no C20 . C21 . 1.344(4) yes C20 . H201 . 0.950 no C21 . H211 . 0.950 no C24 . H241 . 0.950 no C26 . H261 . 0.950 no C31 . H311 . 0.950 no C33 . H331 . 0.950 no O1 . H1 . 0.902 no O1 . H2 . 0.950 no C36 . H361 . 0.950 no C36 . H362 . 0.950 no C36 . H363 . 0.950 no C37 . H371 . 0.950 no C37 . H372 . 0.950 no C37 . H373 . 0.950 no C38 . H381 . 0.950 no C38 . H382 . 0.950 no C38 . H383 . 0.950 no C40 . H401 . 0.950 no C40 . H402 . 0.950 no C40 . H403 . 0.950 no C41 . H411 . 0.950 no C41 . H412 . 0.950 no C41 . H413 . 0.950 no C42 . H421 . 0.950 no C42 . H422 . 0.950 no C42 . H423 . 0.950 no C44 . H441 . 0.950 no C44 . H442 . 0.950 no C44 . H443 . 0.950 no C45 . H451 . 0.950 no C45 . H452 . 0.950 no C45 . H453 . 0.950 no C46 . H461 . 0.950 no C46 . H462 . 0.950 no C46 . H463 . 0.950 no C48 . H481 . 0.950 no C48 . H482 . 0.950 no C48 . H483 . 0.950 no C49 . H491 . 0.950 no C49 . H492 . 0.950 no C49 . H493 . 0.950 no C50 . H501 . 0.950 no C50 . H502 . 0.950 no C50 . H503 . 0.950 no C51 . H511 . 0.950 no C51 . H512 . 0.950 no C51 . C52 . 1.428(7) yes C52 . H521 . 0.950 no C52 . H522 . 0.950 no C52 . C53 . 1.466(8) yes C53 . H531 . 0.950 no C53 . H532 . 0.950 no C53 . C54 . 1.469(7) yes C54 . H541 . 0.950 no C54 . H542 . 0.950 no C61 . H611 . 0.950 no C61 . H612 . 0.950 no C61 . C62 . 1.437(10) yes C62 . H621 . 0.950 no C62 . H622 . 0.950 no C62 . C63 . 1.375(11) yes C63 . H631 . 0.950 no C63 . H632 . 0.950 no C63 . C64 . 1.611(13) yes C64 . H641 . 0.950 no C64 . H642 . 0.950 no C65 . H651 . 0.950 no C65 . H652 . 0.950 no C65 . C66 . 1.452(7) yes C66 . C66 2_556 1.485(10) yes C66 . H661 . 0.950 no C66 . H662 . 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 N1 . Co1 . N2 . 90.62(8) yes N1 . Co1 . N3 . 176.38(7) yes N2 . Co1 . N3 . 89.74(8) yes N1 . Co1 . N4 . 90.34(9) yes N2 . Co1 . N4 . 175.78(8) yes N3 . Co1 . N4 . 89.55(8) yes N1 . Co1 . O2 . 89.22(8) yes N2 . Co1 . O2 . 91.78(7) yes N3 . Co1 . O2 . 87.17(8) yes N4 . Co1 . O2 . 92.35(8) yes N1 . Co1 . O1 . 89.22(12) yes N2 . Co1 . O1 . 87.70(15) yes N3 . Co1 . O1 . 94.40(12) yes N4 . Co1 . O1 . 88.20(16) yes O2 . Co1 . O1 . 178.34(13) yes Co1 . N1 . C1 . 116.98(16) yes Co1 . N1 . C5 . 115.66(16) yes C1 . N1 . C5 . 118.5(2) yes Co1 . N2 . C11 . 125.42(17) yes Co1 . N2 . C13 . 125.60(16) yes C11 . N2 . C13 . 105.36(19) yes Co1 . N3 . C18 . 116.15(15) yes Co1 . N3 . C22 . 115.30(16) yes C18 . N3 . C22 . 118.74(19) yes Co1 . N4 . C28 . 126.32(17) yes Co1 . N4 . C29 . 125.14(16) yes C28 . N4 . C29 . 103.94(19) yes N1 . C1 . C34 . 119.2(2) yes N1 . C1 . C2 . 122.1(2) yes C34 . C1 . C2 . 118.6(2) yes N1 . C5 . C6 . 119.5(2) yes N1 . C5 . C4 . 120.5(2) yes C6 . C5 . C4 . 120.0(2) yes C5 . C6 . C11 . 123.7(2) yes C5 . C6 . C7 . 119.9(2) yes C11 . C6 . C7 . 116.3(2) yes C35 . C8 . C7 . 120.9(3) yes C35 . C8 . C9 . 121.5(2) yes C7 . C8 . C9 . 117.6(2) yes C11 . C10 . C12 . 103.9(2) yes C11 . C10 . C9 . 121.8(3) yes C12 . C10 . C9 . 134.2(2) yes C10 . C11 . C6 . 119.3(2) yes C10 . C11 . N2 . 112.9(2) yes C6 . C11 . N2 . 127.7(2) yes C10 . C12 . C13 . 105.2(2) yes C10 . C12 . C17 . 133.0(2) yes C13 . C12 . C17 . 121.8(2) yes C12 . C13 . N2 . 112.5(2) yes C12 . C13 . C14 . 119.0(2) yes N2 . C13 . C14 . 128.5(2) yes C13 . C14 . C18 . 121.5(2) yes C13 . C14 . C15 . 116.0(2) yes C18 . C14 . C15 . 122.5(2) yes C39 . C16 . C15 . 122.0(3) yes C39 . C16 . C17 . 121.7(2) yes C15 . C16 . C17 . 116.3(2) yes C14 . C18 . N3 . 120.4(2) yes C14 . C18 . C19 . 117.6(2) yes N3 . C18 . C19 . 121.8(2) yes N3 . C22 . C23 . 120.6(2) yes N3 . C22 . C21 . 121.0(2) yes C23 . C22 . C21 . 118.2(2) yes C22 . C23 . C28 . 122.4(2) yes C22 . C23 . C24 . 121.4(2) yes C28 . C23 . C24 . 116.1(2) yes C43 . C25 . C24 . 119.8(2) yes C43 . C25 . C26 . 123.1(2) yes C24 . C25 . C26 . 117.1(2) yes C28 . C27 . C30 . 103.6(2) yes C28 . C27 . C26 . 122.9(2) yes C30 . C27 . C26 . 133.4(2) yes C23 . C28 . C27 . 118.9(2) yes C23 . C28 . N4 . 127.0(2) yes C27 . C28 . N4 . 114.0(2) yes N4 . C29 . C30 . 112.3(2) yes N4 . C29 . C34 . 127.0(2) yes C30 . C29 . C34 . 120.5(2) yes C27 . C30 . C29 . 106.0(2) yes C27 . C30 . C31 . 131.8(2) yes C29 . C30 . C31 . 122.2(3) yes C47 . C32 . C31 . 118.2(3) yes C47 . C32 . C33 . 125.5(3) yes C31 . C32 . C33 . 116.3(2) yes C1 . C34 . C29 . 123.9(2) yes C1 . C34 . C33 . 120.1(3) yes C29 . C34 . C33 . 116.0(2) yes C8 . C35 . C36 . 109.7(3) yes C8 . C35 . C37 . 114.2(4) yes C36 . C35 . C37 . 110.0(5) yes C8 . C35 . C38 . 107.0(3) yes C36 . C35 . C38 . 119.0(6) yes C37 . C35 . C38 . 96.6(4) yes C16 . C39 . C40 . 115.5(3) yes C16 . C39 . C41 . 108.9(3) yes C40 . C39 . C41 . 104.9(3) yes C16 . C39 . C42 . 110.9(2) yes C40 . C39 . C42 . 108.1(3) yes C41 . C39 . C42 . 108.1(3) yes C25 . C43 . C44 . 110.6(2) yes C25 . C43 . C45 . 107.9(2) yes C44 . C43 . C45 . 110.3(3) yes C25 . C43 . C46 . 112.6(2) yes C44 . C43 . C46 . 108.0(2) yes C45 . C43 . C46 . 107.4(2) yes C32 . C47 . C48 . 110.5(3) yes C32 . C47 . C49 . 110.4(3) yes C48 . C47 . C49 . 111.8(4) yes C32 . C47 . C50 . 110.3(3) yes C48 . C47 . C50 . 108.5(4) yes C49 . C47 . C50 . 105.2(4) yes Co1 . O2 . C51 . 124.05(18) yes Co1 . O2 . C54 . 123.9(2) yes C51 . O2 . C54 . 109.7(3) yes C61 . O61 . C64 . 105.3(7) yes C65 2_556 O65 . C65 . 106.9(4) yes C1 . C2 . C3 . 118.5(2) yes C1 . C2 . H21 . 119.5 no C3 . C2 . H21 . 122.0 no C2 . C3 . C4 . 119.3(3) yes C2 . C3 . H31 . 119.7 no C4 . C3 . H31 . 121.0 no C5 . C4 . C3 . 120.0(3) yes C5 . C4 . H41 . 118.9 no C3 . C4 . H41 . 121.0 no C8 . C7 . C6 . 124.9(3) yes C8 . C7 . H71 . 117.2 no C6 . C7 . H71 . 117.9 no C8 . C9 . C10 . 119.9(2) yes C8 . C9 . H91 . 120.3 no C10 . C9 . H91 . 119.8 no C16 . C15 . C14 . 127.4(3) yes C16 . C15 . H151 . 116.3 no C14 . C15 . H151 . 116.3 no C16 . C17 . C12 . 119.5(2) yes C16 . C17 . H171 . 120.5 no C12 . C17 . H171 . 120.0 no C18 . C19 . C20 . 118.3(2) yes C18 . C19 . H191 . 120.4 no C20 . C19 . H191 . 121.2 no C19 . C20 . C21 . 119.5(2) yes C19 . C20 . H201 . 119.7 no C21 . C20 . H201 . 120.8 no C22 . C21 . C20 . 119.9(2) yes C22 . C21 . H211 . 119.4 no C20 . C21 . H211 . 120.7 no C25 . C24 . C23 . 125.6(3) yes C25 . C24 . H241 . 117.9 no C23 . C24 . H241 . 116.5 no C25 . C26 . C27 . 119.3(2) yes C25 . C26 . H261 . 119.6 no C27 . C26 . H261 . 121.0 no C32 . C31 . C30 . 118.9(2) yes C32 . C31 . H311 . 119.9 no C30 . C31 . H311 . 121.2 no C32 . C33 . C34 . 126.0(3) yes C32 . C33 . H331 . 116.1 no C34 . C33 . H331 . 118.0 no Co1 . O1 . H1 . 127.6 no Co1 . O1 . H2 . 130.0 no H1 . O1 . H2 . 90.1 no C35 . C36 . H361 . 110.1 no C35 . C36 . H362 . 116.5 no H361 . C36 . H362 . 109.5 no C35 . C36 . H363 . 101.5 no H361 . C36 . H363 . 109.5 no H362 . C36 . H363 . 109.5 no C35 . C37 . H371 . 110.9 no C35 . C37 . H372 . 107.1 no H371 . C37 . H372 . 109.5 no C35 . C37 . H373 . 110.4 no H371 . C37 . H373 . 109.5 no H372 . C37 . H373 . 109.5 no C35 . C38 . H381 . 110.0 no C35 . C38 . H382 . 108.3 no H381 . C38 . H382 . 109.5 no C35 . C38 . H383 . 110.0 no H381 . C38 . H383 . 109.5 no H382 . C38 . H383 . 109.5 no C39 . C40 . H401 . 112.5 no C39 . C40 . H402 . 105.2 no H401 . C40 . H402 . 109.5 no C39 . C40 . H403 . 110.6 no H401 . C40 . H403 . 109.5 no H402 . C40 . H403 . 109.5 no C39 . C41 . H411 . 109.8 no C39 . C41 . H412 . 107.6 no H411 . C41 . H412 . 109.5 no C39 . C41 . H413 . 111.0 no H411 . C41 . H413 . 109.5 no H412 . C41 . H413 . 109.5 no C39 . C42 . H421 . 111.3 no C39 . C42 . H422 . 106.0 no H421 . C42 . H422 . 109.5 no C39 . C42 . H423 . 111.0 no H421 . C42 . H423 . 109.5 no H422 . C42 . H423 . 109.5 no C43 . C44 . H441 . 109.7 no C43 . C44 . H442 . 108.2 no H441 . C44 . H442 . 109.5 no C43 . C44 . H443 . 110.4 no H441 . C44 . H443 . 109.5 no H442 . C44 . H443 . 109.5 no C43 . C45 . H451 . 109.9 no C43 . C45 . H452 . 108.4 no H451 . C45 . H452 . 109.5 no C43 . C45 . H453 . 110.2 no H451 . C45 . H453 . 109.5 no H452 . C45 . H453 . 109.5 no C43 . C46 . H461 . 111.3 no C43 . C46 . H462 . 107.7 no H461 . C46 . H462 . 109.5 no C43 . C46 . H463 . 109.4 no H461 . C46 . H463 . 109.5 no H462 . C46 . H463 . 109.5 no C47 . C48 . H481 . 110.3 no C47 . C48 . H482 . 110.6 no H481 . C48 . H482 . 109.5 no C47 . C48 . H483 . 107.4 no H481 . C48 . H483 . 109.5 no H482 . C48 . H483 . 109.5 no C47 . C49 . H491 . 110.4 no C47 . C49 . H492 . 108.8 no H491 . C49 . H492 . 109.5 no C47 . C49 . H493 . 109.2 no H491 . C49 . H493 . 109.5 no H492 . C49 . H493 . 109.5 no C47 . C50 . H501 . 109.0 no C47 . C50 . H502 . 110.2 no H501 . C50 . H502 . 109.5 no C47 . C50 . H503 . 109.1 no H501 . C50 . H503 . 109.5 no H502 . C50 . H503 . 109.5 no O2 . C51 . H511 . 109.7 no O2 . C51 . H512 . 110.0 no H511 . C51 . H512 . 109.5 no O2 . C51 . C52 . 105.8(4) yes H511 . C51 . C52 . 113.6 no H512 . C51 . C52 . 108.2 no C51 . C52 . H521 . 108.5 no C51 . C52 . H522 . 112.7 no H521 . C52 . H522 . 109.5 no C51 . C52 . C53 . 105.6(4) yes H521 . C52 . C53 . 109.8 no H522 . C52 . C53 . 110.6 no C52 . C53 . H531 . 112.8 no C52 . C53 . H532 . 110.2 no H531 . C53 . H532 . 109.5 no C52 . C53 . C54 . 104.9(4) yes H531 . C53 . C54 . 108.0 no H532 . C53 . C54 . 111.4 no C53 . C54 . O2 . 107.8(4) yes C53 . C54 . H541 . 112.1 no O2 . C54 . H541 . 110.0 no C53 . C54 . H542 . 109.0 no O2 . C54 . H542 . 108.4 no H541 . C54 . H542 . 109.5 no O61 . C61 . H611 . 111.6 no O61 . C61 . H612 . 110.4 no H611 . C61 . H612 . 109.5 no O61 . C61 . C62 . 103.4(7) yes H611 . C61 . C62 . 111.2 no H612 . C61 . C62 . 110.6 no C61 . C62 . H621 . 109.0 no C61 . C62 . H622 . 109.2 no H621 . C62 . H622 . 109.5 no C61 . C62 . C63 . 111.9(9) yes H621 . C62 . C63 . 108.0 no H622 . C62 . C63 . 109.2 no C62 . C63 . H631 . 111.5 no C62 . C63 . H632 . 110.5 no H631 . C63 . H632 . 109.5 no C62 . C63 . C64 . 103.3(8) yes H631 . C63 . C64 . 111.4 no H632 . C63 . C64 . 110.5 no C63 . C64 . O61 . 109.0(8) yes C63 . C64 . H641 . 108.7 no O61 . C64 . H641 . 110.3 no C63 . C64 . H642 . 109.7 no O61 . C64 . H642 . 109.6 no H641 . C64 . H642 . 109.5 no O65 . C65 . H651 . 109.1 no O65 . C65 . H652 . 107.1 no H651 . C65 . H652 . 109.5 no O65 . C65 . C66 . 110.3(3) yes H651 . C65 . C66 . 114.4 no H652 . C65 . C66 . 106.1 no C66 2_556 C66 . C65 . 106.2(2) yes C66 2_556 C66 . H661 . 106.0 no C65 . C66 . H661 . 105.6 no C66 2_556 C66 . H662 . 116.0 no C65 . C66 . H662 . 112.8 no H661 . C66 . H662 . 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 O1 . H1 . O61 . 173 0.90 1.83 2.728(2) yes # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.048 0.936 0.206 293 46 ' ' 2 -0.033 0.436 0.294 293 46 ' ' 3 -0.095 0.564 0.706 293 46 ' ' 4 -0.023 0.064 0.794 293 46 ' ' _platon_squeeze_details ; ; # Attachment '- arncyc.cif' data_arncyc _database_code_depnum_ccdc_archive 'CCDC 787490' #TrackingRef '- arncyc.cif' _audit_creation_date 10-10-07 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.9009(3) _cell_length_b 22.2751(9) _cell_length_c 29.7836(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5905.3(4) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 2 21 21 ' 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' 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' 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' _cell_formula_units_Z 4 # Given Formula = C67 H88 N4 O5 # Dc = 1.16 Fooo = 2076.40 Mu = 0.72 M = 1029.46 # Found Formula = C64 H79.10 N4 O3.50 # Dc = 1.08 FOOO = 2076.40 Mu = 0.66 M = 960.46 _chemical_formula_sum 'C68 H88 N4 O4.50' _chemical_formula_moiety 'C68 H88 N4 O4.50' _chemical_compound_source ? _chemical_formula_weight 1032.46 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_max 0.34 _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2076.400 _exptl_absorpt_coefficient_mu 0.066 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.76 _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_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 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 27036 _reflns_number_total 11884 _diffrn_reflns_av_R_equivalents 0.046 # Number of reflections with Friedels Law is 11884 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6803 _diffrn_reflns_theta_min 2.930 _diffrn_reflns_theta_max 27.538 _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 25.059 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 38 _reflns_limit_h_min -10 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 28 _reflns_limit_l_min 0 _reflns_limit_l_max 38 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.39 _refine_diff_density_max 0.52 _refine_ls_number_reflns 8509 _refine_ls_number_restraints 0 _refine_ls_number_parameters 663 #_refine_ls_R_factor_ref 0.0532 _refine_ls_wR_factor_ref 0.0578 _refine_ls_goodness_of_fit_ref 0.8998 #_reflns_number_all 11884 _refine_ls_R_factor_all 0.0866 _refine_ls_wR_factor_all 0.2512 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 8509 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_gt 0.0578 _refine_ls_shift/su_max 0.000601 # 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 unk _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: 1.51 1.75 0.779 ; # 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. Blessing, SORTAV ( ) 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. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. 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 N1 N 0.37124(18) 0.37099(7) 0.65115(4) 0.0447 1.0000 Uani . . . . . . N3 N -0.06591(17) 0.24015(7) 0.65303(4) 0.0445 1.0000 Uani . . . . . . C1 C 0.3873(3) 0.40533(9) 0.68782(6) 0.0534 1.0000 Uani . . . . . . C5 C 0.3939(2) 0.39644(8) 0.61121(5) 0.0458 1.0000 Uani . . . . . . C6 C 0.3983(2) 0.35740(7) 0.57088(5) 0.0444 1.0000 Uani . . . . . . C8 C 0.5175(2) 0.33076(9) 0.49914(5) 0.0452 1.0000 Uani . . . . . . C10 C 0.2967(2) 0.27799(8) 0.52255(5) 0.0438 1.0000 Uani . . . . . . C11 C 0.2928(2) 0.31171(8) 0.56295(5) 0.0420 1.0000 Uani . . . . . . C12 C 0.0875(2) 0.25154(7) 0.56383(5) 0.0413 1.0000 Uani . . . . . . C13 C 0.1651(2) 0.24034(8) 0.52242(5) 0.0448 1.0000 Uani . . . . . . C15 C -0.0270(2) 0.17008(9) 0.50076(6) 0.0493 1.0000 Uani . . . . . . C17 C -0.0477(2) 0.22434(8) 0.57313(5) 0.0431 1.0000 Uani . . . . . . C18 C -0.1414(2) 0.23771(8) 0.61380(5) 0.0439 1.0000 Uani . . . . . . C22 C -0.1486(2) 0.24814(9) 0.69093(5) 0.0477 1.0000 Uani . . . . . . C23 C -0.0716(2) 0.24548(9) 0.73507(6) 0.0477 1.0000 Uani . . . . . . C25 C -0.0673(2) 0.20606(11) 0.81258(6) 0.0554 1.0000 Uani . . . . . . C27 C 0.1317(2) 0.26908(8) 0.78672(5) 0.0446 1.0000 Uani . . . . . . C28 C 0.0625(2) 0.27407(8) 0.74400(5) 0.0452 1.0000 Uani . . . . . . C29 C 0.2693(2) 0.33296(8) 0.74322(5) 0.0446 1.0000 Uani . . . . . . C30 C 0.2652(2) 0.30649(8) 0.78655(5) 0.0445 1.0000 Uani . . . . . . C32 C 0.4847(2) 0.36163(9) 0.80872(6) 0.0523 1.0000 Uani . . . . . . C34 C 0.3793(2) 0.37647(8) 0.73259(5) 0.0493 1.0000 Uani . . . . . . C35 C 0.6468(2) 0.34445(9) 0.46631(5) 0.0481 1.0000 Uani . . . . . . C39 C -0.0869(3) 0.12397(10) 0.46690(7) 0.0581 1.0000 Uani . . . . . . C43 C -0.1412(3) 0.16412(15) 0.84858(6) 0.0812 1.0000 Uani . . . . . . C47 C 0.6065(3) 0.38102(11) 0.84216(6) 0.0632 1.0000 Uani . . . . . . C2 C 0.4144(3) 0.46748(9) 0.68590(6) 0.0645 1.0000 Uani . . . . . . C3 C 0.4342(3) 0.49326(9) 0.64393(6) 0.0619 1.0000 Uani . . . . . . C4 C 0.4223(3) 0.45881(9) 0.60604(6) 0.0548 1.0000 Uani . . . . . . C7 C 0.5083(2) 0.36589(8) 0.53781(5) 0.0427 1.0000 Uani . . . . . . C9 C 0.4098(2) 0.28787(8) 0.49147(5) 0.0444 1.0000 Uani . . . . . . C14 C 0.1080(2) 0.19902(8) 0.49223(5) 0.0441 1.0000 Uani . . . . . . C16 C -0.1027(2) 0.18322(8) 0.54093(6) 0.0493 1.0000 Uani . . . . . . C19 C -0.2939(2) 0.24500(9) 0.61000(6) 0.0488 1.0000 Uani . . . . . . C20 C -0.3760(2) 0.25683(9) 0.64810(6) 0.0517 1.0000 Uani . . . . . . C21 C -0.3024(2) 0.25796(9) 0.68930(6) 0.0501 1.0000 Uani . . . . . . C24 C -0.1320(2) 0.21117(10) 0.76920(6) 0.0508 1.0000 Uani . . . . . . C26 C 0.0665(2) 0.23433(10) 0.81989(6) 0.0527 1.0000 Uani . . . . . . C31 C 0.3726(2) 0.32116(9) 0.81877(5) 0.0506 1.0000 Uani . . . . . . C33 C 0.4824(2) 0.38918(9) 0.76512(5) 0.0520 1.0000 Uani . . . . . . N2 N 0.16638(17) 0.29502(7) 0.58720(4) 0.0441 1.0000 Uani . . . . . . N4 N 0.15180(18) 0.31133(7) 0.71742(5) 0.0459 1.0000 Uani . . . . . . H21 H 0.4199 0.4910 0.7124 0.0873 1.0000 Uiso R . . . . . H31 H 0.4565 0.5349 0.6416 0.0916 1.0000 Uiso R . . . . . H41 H 0.4323 0.4761 0.5770 0.0824 1.0000 Uiso R . . . . . H71 H 0.5805 0.3967 0.5424 0.0603 1.0000 Uiso R . . . . . H91 H 0.4134 0.2639 0.4651 0.0578 1.0000 Uiso R . . . . . H141 H 0.1618 0.1904 0.4654 0.0635 1.0000 Uiso R . . . . . H161 H -0.1945 0.1630 0.5469 0.0696 1.0000 Uiso R . . . . . H191 H -0.3402 0.2428 0.5813 0.0671 1.0000 Uiso R . . . . . H201 H -0.4810 0.2641 0.6462 0.0747 1.0000 Uiso R . . . . . H211 H -0.3565 0.2650 0.7163 0.0739 1.0000 Uiso R . . . . . H241 H -0.2230 0.1905 0.7631 0.0761 1.0000 Uiso R . . . . . H261 H 0.1131 0.2314 0.8485 0.0708 1.0000 Uiso R . . . . . H311 H 0.3692 0.3028 0.8475 0.0681 1.0000 Uiso R . . . . . H331 H 0.5581 0.4178 0.7581 0.0775 1.0000 Uiso R . . . . . H1 H 0.1382 0.3114 0.6173 0.0594 1.0000 Uiso R . . . . . H2 H 0.1341 0.3209 0.6850 0.0554 1.0000 Uiso R . . . . . C36 C 0.7987(2) 0.33417(12) 0.48852(7) 0.0612 1.0000 Uani . . . . . . H361 H 0.8772 0.3425 0.4679 0.0879 1.0000 Uiso R . . . . . H362 H 0.8070 0.3602 0.5137 0.0879 1.0000 Uiso R . . . . . H363 H 0.8061 0.2937 0.4983 0.0879 1.0000 Uiso R . . . . . C37 C 0.6408(3) 0.30469(10) 0.42454(7) 0.0610 1.0000 Uani . . . . . . H371 H 0.7226 0.3136 0.4052 0.0855 1.0000 Uiso R . . . . . H372 H 0.6452 0.2637 0.4331 0.0855 1.0000 Uiso R . . . . . H373 H 0.5489 0.3122 0.4093 0.0855 1.0000 Uiso R . . . . . C38 C 0.6360(3) 0.41088(10) 0.45047(7) 0.0619 1.0000 Uani . . . . . . H381 H 0.7154 0.4204 0.4304 0.0945 1.0000 Uiso R . . . . . H382 H 0.6399 0.4370 0.4756 0.0945 1.0000 Uiso R . . . . . H383 H 0.5424 0.4156 0.4355 0.0945 1.0000 Uiso R . . . . . C40 C 0.0290(4) 0.07336(14) 0.45958(14) 0.1054 1.0000 Uani . . . . . . H401 H 0.0433 0.0505 0.4862 0.1468 1.0000 Uiso R . . . . . H402 H 0.1213 0.0916 0.4512 0.1468 1.0000 Uiso R . . . . . H403 H -0.0043 0.0477 0.4361 0.1468 1.0000 Uiso R . . . . . C41 C -0.0981(5) 0.15431(15) 0.41947(8) 0.1032 1.0000 Uani . . . . . . H411 H -0.0025 0.1715 0.4134 0.1529 1.0000 Uiso R . . . . . H412 H -0.1726 0.1848 0.4188 0.1529 1.0000 Uiso R . . . . . H413 H -0.1203 0.1249 0.3974 0.1529 1.0000 Uiso R . . . . . C42 C -0.2271(6) 0.0968(2) 0.47985(15) 0.1643 1.0000 Uani . . . . . . H421 H -0.2145 0.0800 0.5089 0.1788 1.0000 Uiso R . . . . . H422 H -0.3050 0.1260 0.4806 0.1788 1.0000 Uiso R . . . . . H423 H -0.2527 0.0660 0.4592 0.1788 1.0000 Uiso R . . . . . C44 C -0.0646(7) 0.10469(19) 0.84787(19) 0.1874 1.0000 Uani . . . . . . H441 H -0.1087 0.0799 0.8703 0.2950 1.0000 Uiso R . . . . . H442 H 0.0393 0.1097 0.8541 0.2950 1.0000 Uiso R . . . . . H443 H -0.0765 0.0864 0.8193 0.2950 1.0000 Uiso R . . . . . C45 C -0.1272(5) 0.1969(2) 0.89523(9) 0.1249 1.0000 Uani . . . . . . H451 H -0.1700 0.1719 0.9177 0.1324 1.0000 Uiso R . . . . . H452 H -0.0255 0.2052 0.9026 0.1324 1.0000 Uiso R . . . . . H453 H -0.1819 0.2335 0.8936 0.1324 1.0000 Uiso R . . . . . C46 C -0.3096(4) 0.1586(2) 0.84156(10) 0.1064 1.0000 Uani . . . . . . H461 H -0.3513 0.1332 0.8640 0.1538 1.0000 Uiso R . . . . . H462 H -0.3526 0.1975 0.8439 0.1538 1.0000 Uiso R . . . . . H463 H -0.3306 0.1424 0.8127 0.1538 1.0000 Uiso R . . . . . C48 C 0.7604(3) 0.36772(17) 0.82305(9) 0.0905 1.0000 Uani . . . . . . H481 H 0.8344 0.3802 0.8440 0.1210 1.0000 Uiso R . . . . . H482 H 0.7699 0.3258 0.8178 0.1210 1.0000 Uiso R . . . . . H483 H 0.7739 0.3888 0.7956 0.1210 1.0000 Uiso R . . . . . C49 C 0.5905(4) 0.34741(14) 0.88684(7) 0.0817 1.0000 Uani . . . . . . H491 H 0.6672 0.3608 0.9066 0.1103 1.0000 Uiso R . . . . . H492 H 0.4950 0.3558 0.8996 0.1103 1.0000 Uiso R . . . . . H493 H 0.6002 0.3054 0.8822 0.1103 1.0000 Uiso R . . . . . C50 C 0.5945(5) 0.45037(14) 0.85089(9) 0.1054 1.0000 Uani . . . . . . H501 H 0.6704 0.4618 0.8716 0.1365 1.0000 Uiso R . . . . . H502 H 0.4985 0.4589 0.8633 0.1365 1.0000 Uiso R . . . . . H503 H 0.6068 0.4722 0.8237 0.1365 1.0000 Uiso R . . . . . O51 O 0.0049(3) 0.38726(11) 0.65016(7) 0.1042 1.0000 Uani . . . . . . C51 C -0.0687(9) 0.4053(2) 0.61462(15) 0.1683 1.0000 Uani . . . . . . H511 H -0.1370 0.3734 0.6090 0.1837 1.0000 Uiso R . . . . . H512 H -0.0030 0.4097 0.5897 0.1837 1.0000 Uiso R . . . . . C52 C -0.1589(9) 0.4547(3) 0.6212(2) 0.1913 1.0000 Uani . . . . . . H521 H -0.1051 0.4892 0.6115 0.2562 1.0000 Uiso R . . . . . H522 H -0.2537 0.4534 0.6065 0.2562 1.0000 Uiso R . . . . . C53 C -0.1747(11) 0.4512(4) 0.6710(3) 0.2193 1.0000 Uani . . . . . . H531 H -0.1978 0.4894 0.6833 0.2826 1.0000 Uiso R . . . . . H532 H -0.2511 0.4234 0.6790 0.2826 1.0000 Uiso R . . . . . C54 C -0.0517(13) 0.4229(4) 0.68593(19) 0.2460 1.0000 Uani . . . . . . H541 H -0.0596 0.4030 0.7140 0.2313 1.0000 Uiso R . . . . . H542 H 0.0196 0.4545 0.6882 0.2313 1.0000 Uiso R . . . . . O61 O 0.3161(2) 0.5000 0.5000 0.0601 1.0000 Uani S T . . . . C61 C 0.2224(3) 0.45320(12) 0.48352(8) 0.0713 1.0000 Uani . . . . . . H611 H 0.2036 0.4173 0.4998 0.0992 1.0000 Uiso R . . . . . H612 H 0.2036 0.4465 0.4525 0.0992 1.0000 Uiso R . . . . . C62 C 0.0703(9) 0.4613(3) 0.5033(3) 0.0873 0.5000 Uani . . . . . . H621 H 0.0541 0.4316 0.5257 0.1008 0.5000 Uiso R . . . . . H622 H -0.0057 0.4583 0.4811 0.1008 0.5000 Uiso R . . . . . C63 C 0.0690(10) 0.4797(4) 0.4770(4) 0.1072 0.5000 Uani . . . . . . H631 H -0.0064 0.4556 0.4906 0.1008 0.5000 Uiso R . . . . . H632 H 0.0502 0.4826 0.4457 0.1008 0.5000 Uiso R . . . . . O81 O 0.1919(8) 0.5094(3) 0.1362(2) 0.1630 0.7000 Uani . . . . . . O82 O 0.037(2) 0.4978(10) 0.1501(8) 0.2050 0.3000 Uani . . . . . . C81 C 0.1513(11) 0.4451(4) 0.1330(3) 0.2051 1.0000 Uani . . . . . . H811 H 0.2514 0.4452 0.1219 0.2202 1.0000 Uiso R . . . . . H812 H 0.1049 0.4272 0.1087 0.2202 1.0000 Uiso R . . . . . C82 C 0.1771(10) 0.4161(4) 0.1752(3) 0.1862 1.0000 Uani . . . . . . H821 H 0.0780 0.4013 0.1794 0.2259 1.0000 Uiso R . . . . . H822 H 0.2233 0.3808 0.1760 0.2259 1.0000 Uiso R . . . . . C83 C 0.1961(9) 0.4659(3) 0.2099(3) 0.1718 1.0000 Uani . . . . . . H831 H 0.3003 0.4671 0.2167 0.2162 1.0000 Uiso R . . . . . H832 H 0.1380 0.4572 0.2386 0.2162 1.0000 Uiso R . . . . . C84 C 0.1324(9) 0.5185(3) 0.1818(3) 0.1620 1.0000 Uani . . . . . . H841 H 0.2085 0.5484 0.1825 0.1634 1.0000 Uiso R . . . . . H842 H 0.0514 0.5372 0.1960 0.1634 1.0000 Uiso R . . . . . O91 O 0.2986(5) 0.0450(2) 0.55111(14) 0.1673 1.0000 Uani . . . . . . C91 C 0.4307(8) 0.0624(4) 0.5352(3) 0.1908 1.0000 Uani . . . . . . H911 H 0.4994 0.0299 0.5328 0.2480 1.0000 Uiso R . . . . . H912 H 0.4107 0.0834 0.5103 0.2480 1.0000 Uiso R . . . . . C92 C 0.4810(10) 0.1253(4) 0.5503(3) 0.1969 1.0000 Uani . . . . . . H921 H 0.5446 0.1066 0.5718 0.2490 1.0000 Uiso R . . . . . H922 H 0.5415 0.1442 0.5609 0.2490 1.0000 Uiso R . . . . . C93 C 0.3973(7) 0.1326(3) 0.5879(2) 0.1633 1.0000 Uani . . . . . . H931 H 0.4120 0.1364 0.6194 0.2122 1.0000 Uiso R . . . . . H932 H 0.3518 0.1675 0.5789 0.2122 1.0000 Uiso R . . . . . C94 C 0.2577(7) 0.0908(3) 0.58513(19) 0.1604 1.0000 Uani . . . . . . H941 H 0.2315 0.0709 0.6123 0.2110 1.0000 Uiso R . . . . . H942 H 0.1760 0.1124 0.5731 0.2110 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 N1 0.0598(8) 0.0461(8) 0.0281(6) -0.0019(5) -0.0007(6) -0.0040(6) N3 0.0499(7) 0.0556(8) 0.0279(6) 0.0026(5) 0.0027(6) -0.0076(6) C1 0.0832(14) 0.0478(9) 0.0292(7) -0.0037(6) -0.0008(8) -0.0053(9) C5 0.0612(11) 0.0485(9) 0.0277(7) -0.0024(6) -0.0013(7) -0.0089(8) C6 0.0659(11) 0.0379(8) 0.0294(7) 0.0062(6) -0.0013(7) -0.0038(7) C8 0.0546(9) 0.0540(9) 0.0269(7) -0.0001(7) 0.0000(7) -0.0029(8) C10 0.0574(10) 0.0486(9) 0.0254(7) -0.0041(6) 0.0003(6) -0.0057(7) C11 0.0551(10) 0.0450(8) 0.0261(7) 0.0019(6) -0.0029(6) -0.0067(7) C12 0.0536(9) 0.0437(8) 0.0267(6) 0.0031(6) -0.0007(6) 0.0000(7) C13 0.0591(10) 0.0413(8) 0.0341(7) -0.0042(6) -0.0002(7) -0.0027(7) C15 0.0700(11) 0.0492(9) 0.0288(7) -0.0037(7) 0.0017(7) 0.0034(8) C17 0.0529(9) 0.0503(9) 0.0261(7) 0.0045(6) -0.0015(6) 0.0013(7) C18 0.0542(10) 0.0488(8) 0.0288(7) 0.0005(6) 0.0020(7) -0.0061(8) C22 0.0516(10) 0.0630(11) 0.0285(7) -0.0028(7) 0.0014(7) -0.0059(8) C23 0.0452(9) 0.0671(11) 0.0308(7) 0.0042(7) 0.0019(7) 0.0002(8) C25 0.0582(11) 0.0748(12) 0.0332(8) 0.0071(8) 0.0030(8) -0.0067(10) C27 0.0521(9) 0.0544(9) 0.0275(7) 0.0046(6) -0.0008(7) 0.0005(8) C28 0.0496(9) 0.0569(10) 0.0292(7) 0.0023(6) 0.0006(7) 0.0019(8) C29 0.0593(10) 0.0494(9) 0.0252(7) 0.0001(6) -0.0009(7) -0.0038(8) C30 0.0544(10) 0.0534(9) 0.0258(7) 0.0008(6) -0.0002(6) -0.0010(8) C32 0.0683(12) 0.0605(11) 0.0280(7) -0.0055(7) -0.0036(8) -0.0110(9) C34 0.0717(12) 0.0507(9) 0.0255(7) -0.0026(6) -0.0024(7) -0.0124(9) C35 0.0525(10) 0.0581(10) 0.0338(7) 0.0044(7) 0.0099(7) 0.0029(8) C39 0.0694(12) 0.0600(11) 0.0450(9) -0.0065(8) 0.0029(9) -0.0086(10) C43 0.0985(18) 0.117(2) 0.0285(8) 0.0130(11) -0.0083(10) -0.0437(16) C47 0.0839(15) 0.0715(13) 0.0343(9) 0.0041(8) -0.0154(9) -0.0249(11) C2 0.1119(18) 0.0486(10) 0.0329(8) -0.0052(7) 0.0027(10) -0.0120(11) C3 0.1021(16) 0.0480(10) 0.0356(9) -0.0031(7) 0.0019(10) -0.0095(11) C4 0.0826(13) 0.0498(10) 0.0318(8) 0.0002(7) -0.0039(8) -0.0087(9) C7 0.0547(9) 0.0415(8) 0.0319(7) 0.0053(6) -0.0058(7) -0.0123(7) C9 0.0652(11) 0.0444(8) 0.0237(6) -0.0021(6) 0.0006(7) 0.0012(8) C14 0.0474(9) 0.0600(10) 0.0251(6) -0.0059(6) -0.0011(6) -0.0041(8) C16 0.0564(10) 0.0500(9) 0.0413(8) 0.0036(7) -0.0118(8) -0.0069(8) C19 0.0573(11) 0.0584(10) 0.0307(7) 0.0039(7) -0.0048(7) -0.0031(8) C20 0.0531(10) 0.0614(11) 0.0404(8) 0.0036(7) -0.0034(8) 0.0081(8) C21 0.0545(10) 0.0606(11) 0.0353(8) -0.0071(7) 0.0014(7) 0.0064(8) C24 0.0468(9) 0.0706(11) 0.0349(8) 0.0050(8) 0.0065(7) -0.0011(9) C26 0.0572(10) 0.0694(12) 0.0316(8) 0.0106(7) 0.0006(7) -0.0027(9) C31 0.0630(11) 0.0621(11) 0.0268(7) 0.0014(7) -0.0034(7) -0.0068(9) C33 0.0744(13) 0.0546(10) 0.0269(7) -0.0073(7) -0.0012(8) -0.0134(9) N2 0.0549(8) 0.0486(8) 0.0287(6) -0.0067(5) 0.0050(6) -0.0084(6) N4 0.0548(8) 0.0554(8) 0.0274(6) 0.0026(6) -0.0020(6) -0.0023(7) C36 0.0607(12) 0.0804(14) 0.0426(9) 0.0051(9) 0.0010(9) -0.0048(10) C37 0.0712(13) 0.0704(13) 0.0415(9) -0.0207(9) 0.0103(9) -0.0096(10) C38 0.0726(13) 0.0603(11) 0.0528(10) 0.0176(9) 0.0156(10) -0.0004(10) C40 0.117(2) 0.0730(17) 0.126(3) -0.0541(18) -0.025(2) -0.0003(16) C41 0.175(3) 0.0930(19) 0.0417(11) -0.0231(12) -0.0234(16) 0.001(2) C42 0.161(4) 0.208(5) 0.124(3) -0.128(3) 0.052(3) -0.111(4) C44 0.260(6) 0.105(3) 0.197(5) 0.104(3) 0.162(5) 0.079(3) C45 0.138(3) 0.196(4) 0.0406(12) 0.0180(17) -0.0004(14) -0.081(3) C46 0.117(2) 0.140(3) 0.0621(15) 0.0179(17) 0.0220(16) -0.051(2) C48 0.0796(17) 0.130(3) 0.0623(14) 0.0192(15) -0.0237(13) -0.0484(17) C49 0.1012(19) 0.1040(19) 0.0399(10) 0.0120(11) -0.0189(12) -0.0310(16) C50 0.183(3) 0.0764(16) 0.0564(14) -0.0071(12) -0.0519(19) -0.028(2) O51 0.149(2) 0.0936(14) 0.0699(11) 0.0087(10) -0.0194(13) 0.0444(14) C51 0.278(7) 0.136(3) 0.091(3) -0.003(2) -0.060(4) 0.102(5) C52 0.238(7) 0.198(6) 0.138(4) 0.003(4) -0.049(5) 0.138(6) C53 0.233(8) 0.235(8) 0.190(7) 0.037(6) 0.077(6) 0.129(7) C54 0.409(13) 0.227(7) 0.102(3) -0.044(4) -0.077(5) 0.210(9) O61 0.0654(12) 0.0711(13) 0.0439(10) -0.0158(9) 0.0000 0.0000 C61 0.0780(15) 0.0780(15) 0.0580(13) -0.0121(11) -0.0069(11) -0.0108(12) C62 0.071(3) 0.069(4) 0.122(6) 0.003(4) 0.006(4) -0.026(3) C63 0.096(5) 0.090(5) 0.136(7) -0.032(5) -0.034(6) -0.020(4) O81 0.188(6) 0.147(4) 0.154(5) -0.016(4) -0.010(4) 0.033(4) O82 0.187(15) 0.200(16) 0.228(18) 0.008(15) 0.016(16) 0.019(14) C81 0.220(9) 0.192(8) 0.203(8) -0.014(7) -0.001(7) -0.038(7) C82 0.202(7) 0.164(6) 0.193(7) 0.019(6) 0.032(6) -0.004(5) C83 0.165(5) 0.161(5) 0.190(6) 0.000(5) 0.007(5) 0.003(4) C84 0.159(5) 0.165(6) 0.162(6) 0.014(4) 0.016(5) 0.006(4) O91 0.168(3) 0.172(3) 0.163(3) 0.054(3) 0.058(3) 0.070(3) C91 0.172(5) 0.195(7) 0.206(7) 0.065(6) 0.085(5) 0.078(5) C92 0.217(7) 0.179(6) 0.195(7) 0.056(5) 0.092(6) 0.057(6) C93 0.167(5) 0.172(5) 0.151(5) 0.065(4) 0.044(4) 0.070(4) C94 0.162(4) 0.166(5) 0.153(4) 0.085(4) 0.060(4) 0.088(4) _refine_ls_extinction_method None 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 N1 . C1 . 1.341(2) yes N1 . C5 . 1.333(2) yes N3 . C18 . 1.349(2) yes N3 . C22 . 1.359(2) yes C1 . C34 . 1.482(2) yes C1 . C2 . 1.406(3) yes C5 . C6 . 1.483(2) yes C5 . C4 . 1.420(3) yes C6 . C11 . 1.405(2) yes C6 . C7 . 1.401(3) yes C8 . C35 . 1.540(2) yes C8 . C7 . 1.395(2) yes C8 . C9 . 1.373(3) yes C10 . C11 . 1.419(2) yes C10 . C13 . 1.441(3) yes C10 . C9 . 1.385(2) yes C11 . N2 . 1.388(2) yes C12 . C13 . 1.435(2) yes C12 . C17 . 1.375(3) yes C12 . N2 . 1.384(2) yes C13 . C14 . 1.383(2) yes C15 . C39 . 1.535(3) yes C15 . C14 . 1.387(3) yes C15 . C16 . 1.404(3) yes C17 . C18 . 1.501(2) yes C17 . C16 . 1.414(2) yes C18 . C19 . 1.372(3) yes C22 . C23 . 1.484(2) yes C22 . C21 . 1.387(3) yes C23 . C28 . 1.378(3) yes C23 . C24 . 1.381(3) yes C25 . C43 . 1.567(3) yes C25 . C24 . 1.419(3) yes C25 . C26 . 1.365(3) yes C27 . C28 . 1.418(2) yes C27 . C30 . 1.451(3) yes C27 . C26 . 1.383(2) yes C28 . N4 . 1.396(2) yes C29 . C30 . 1.419(2) yes C29 . C34 . 1.414(3) yes C29 . N4 . 1.384(2) yes C30 . C31 . 1.393(2) yes C32 . C47 . 1.534(3) yes C32 . C31 . 1.378(3) yes C32 . C33 . 1.436(2) yes C34 . C33 . 1.365(3) yes C35 . C36 . 1.523(3) yes C35 . C37 . 1.528(2) yes C35 . C38 . 1.556(3) yes C39 . C40 . 1.544(4) yes C39 . C41 . 1.569(4) yes C39 . C42 . 1.439(5) yes C43 . C44 . 1.489(5) yes C43 . C45 . 1.575(4) yes C43 . C46 . 1.519(5) yes C47 . C48 . 1.512(4) yes C47 . C49 . 1.534(3) yes C47 . C50 . 1.570(4) yes C2 . C3 . 1.387(3) yes C2 . H21 . 0.950 no C3 . C4 . 1.369(3) yes C3 . H31 . 0.950 no C4 . H41 . 0.950 no C7 . H71 . 0.950 no C9 . H91 . 0.950 no C14 . H141 . 0.950 no C16 . H161 . 0.950 no C19 . C20 . 1.375(3) yes C19 . H191 . 0.950 no C20 . C21 . 1.391(3) yes C20 . H201 . 0.950 no C21 . H211 . 0.950 no C24 . H241 . 0.950 no C26 . H261 . 0.950 no C31 . H311 . 0.950 no C33 . H331 . 0.950 no N2 . H1 . 1.000 no N4 . H2 . 1.000 no C36 . H361 . 0.950 no C36 . H362 . 0.950 no C36 . H363 . 0.950 no C37 . H371 . 0.950 no C37 . H372 . 0.950 no C37 . H373 . 0.950 no C38 . H381 . 0.950 no C38 . H382 . 0.950 no C38 . H383 . 0.950 no C40 . H401 . 0.950 no C40 . H402 . 0.950 no C40 . H403 . 0.950 no C41 . H411 . 0.950 no C41 . H412 . 0.950 no C41 . H413 . 0.950 no C42 . H421 . 0.950 no C42 . H422 . 0.950 no C42 . H423 . 0.950 no C44 . H441 . 0.950 no C44 . H442 . 0.950 no C44 . H443 . 0.950 no C45 . H451 . 0.950 no C45 . H452 . 0.950 no C45 . H453 . 0.950 no C46 . H461 . 0.950 no C46 . H462 . 0.950 no C46 . H463 . 0.950 no C48 . H481 . 0.950 no C48 . H482 . 0.950 no C48 . H483 . 0.950 no C49 . H491 . 0.950 no C49 . H492 . 0.950 no C49 . H493 . 0.950 no C50 . H501 . 0.950 no C50 . H502 . 0.950 no C50 . H503 . 0.950 no O51 . C51 . 1.308(4) yes O51 . C54 . 1.421(6) yes C51 . H511 . 0.950 no C51 . H512 . 0.950 no C51 . C52 . 1.376(7) yes C52 . H521 . 0.950 no C52 . H522 . 0.950 no C52 . C53 . 1.493(9) yes C53 . H531 . 0.950 no C53 . H532 . 0.950 no C53 . C54 . 1.338(10) yes C54 . H541 . 0.950 no C54 . H542 . 0.950 no O61 . C61 2_566 1.422(3) yes O61 . C61 . 1.422(3) yes C61 . H611 . 0.950 no C61 . H612 . 0.950 no C61 . C62 . 1.488(8) yes C61 . C63 . 1.501(10) yes C62 . C63 2_566 1.438(8) yes C62 . C62 2_566 1.735(14) yes C62 . H621 . 0.950 no C62 . H622 . 0.950 no C62 . C63 . 0.886(11) yes C62 . H631 . 0.791 no H622 . C63 . 0.827 no C63 . C63 2_566 1.642(18) yes C63 . H631 . 0.950 no C63 . H632 . 0.950 no O81 . O82 . 1.47(2) yes O81 . C81 . 1.480(11) yes O81 . C84 . 1.474(9) yes O82 . C81 . 1.64(2) yes O82 . C84 . 1.35(2) yes C81 . H811 . 0.950 no C81 . H812 . 0.924 no C81 . C82 . 1.434(10) yes C82 . H821 . 0.950 no C82 . H822 . 0.887 no C82 . C83 . 1.525(10) yes C83 . H831 . 0.950 no C83 . H832 . 1.018 no C83 . C84 . 1.547(9) yes C84 . H841 . 0.950 no C84 . H842 . 0.934 no O91 . C91 . 1.326(8) yes O91 . C94 . 1.483(7) yes C91 . H911 . 0.950 no C91 . H912 . 0.896 no C91 . C92 . 1.538(12) yes C92 . H921 . 0.950 no C92 . H922 . 0.753 no C92 . C93 . 1.355(7) yes C93 . H931 . 0.950 no C93 . H932 . 0.918 no C93 . C94 . 1.556(9) yes C94 . H941 . 0.950 no C94 . H942 . 0.943 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 C1 . N1 . C5 . 117.90(15) yes C18 . N3 . C22 . 117.08(15) yes N1 . C1 . C34 . 118.69(16) yes N1 . C1 . C2 . 123.15(16) yes C34 . C1 . C2 . 118.15(15) yes N1 . C5 . C6 . 118.50(15) yes N1 . C5 . C4 . 122.65(15) yes C6 . C5 . C4 . 118.75(14) yes C5 . C6 . C11 . 122.90(16) yes C5 . C6 . C7 . 120.57(16) yes C11 . C6 . C7 . 116.51(15) yes C35 . C8 . C7 . 117.20(16) yes C35 . C8 . C9 . 123.64(15) yes C7 . C8 . C9 . 119.12(16) yes C11 . C10 . C13 . 106.89(14) yes C11 . C10 . C9 . 120.02(15) yes C13 . C10 . C9 . 132.98(14) yes C10 . C11 . C6 . 120.66(15) yes C10 . C11 . N2 . 108.62(14) yes C6 . C11 . N2 . 130.43(15) yes C13 . C12 . C17 . 121.15(15) yes C13 . C12 . N2 . 108.05(14) yes C17 . C12 . N2 . 130.60(15) yes C10 . C13 . C12 . 106.72(14) yes C10 . C13 . C14 . 133.42(16) yes C12 . C13 . C14 . 119.86(17) yes C39 . C15 . C14 . 119.43(16) yes C39 . C15 . C16 . 122.20(18) yes C14 . C15 . C16 . 118.36(16) yes C12 . C17 . C18 . 124.15(15) yes C12 . C17 . C16 . 116.88(16) yes C18 . C17 . C16 . 118.91(16) yes C17 . C18 . N3 . 115.50(16) yes C17 . C18 . C19 . 120.45(15) yes N3 . C18 . C19 . 124.02(15) yes N3 . C22 . C23 . 118.73(16) yes N3 . C22 . C21 . 121.72(16) yes C23 . C22 . C21 . 119.55(15) yes C22 . C23 . C28 . 123.53(16) yes C22 . C23 . C24 . 119.65(17) yes C28 . C23 . C24 . 116.77(16) yes C43 . C25 . C24 . 120.06(19) yes C43 . C25 . C26 . 122.15(17) yes C24 . C25 . C26 . 117.52(17) yes C28 . C27 . C30 . 107.93(14) yes C28 . C27 . C26 . 120.13(17) yes C30 . C27 . C26 . 131.90(15) yes C27 . C28 . C23 . 120.89(16) yes C27 . C28 . N4 . 107.92(15) yes C23 . C28 . N4 . 131.18(15) yes C30 . C29 . C34 . 120.39(15) yes C30 . C29 . N4 . 109.95(15) yes C34 . C29 . N4 . 129.61(15) yes C27 . C30 . C29 . 105.21(14) yes C27 . C30 . C31 . 133.94(15) yes C29 . C30 . C31 . 120.77(16) yes C47 . C32 . C31 . 123.72(16) yes C47 . C32 . C33 . 118.47(17) yes C31 . C32 . C33 . 117.74(16) yes C1 . C34 . C29 . 122.17(16) yes C1 . C34 . C33 . 121.08(18) yes C29 . C34 . C33 . 116.70(15) yes C8 . C35 . C36 . 110.96(14) yes C8 . C35 . C37 . 112.09(16) yes C36 . C35 . C37 . 107.31(17) yes C8 . C35 . C38 . 109.56(16) yes C36 . C35 . C38 . 109.23(18) yes C37 . C35 . C38 . 107.59(16) yes C15 . C39 . C40 . 110.45(19) yes C15 . C39 . C41 . 108.98(18) yes C40 . C39 . C41 . 103.3(2) yes C15 . C39 . C42 . 113.94(19) yes C40 . C39 . C42 . 108.1(3) yes C41 . C39 . C42 . 111.5(3) yes C25 . C43 . C44 . 109.2(2) yes C25 . C43 . C45 . 107.1(2) yes C44 . C43 . C45 . 112.9(4) yes C25 . C43 . C46 . 111.6(2) yes C44 . C43 . C46 . 112.2(4) yes C45 . C43 . C46 . 103.7(3) yes C32 . C47 . C48 . 109.90(18) yes C32 . C47 . C49 . 111.11(18) yes C48 . C47 . C49 . 108.4(2) yes C32 . C47 . C50 . 109.6(2) yes C48 . C47 . C50 . 108.5(3) yes C49 . C47 . C50 . 109.3(2) yes C1 . C2 . C3 . 117.78(17) yes C1 . C2 . H21 . 121.3 no C3 . C2 . H21 . 121.0 no C2 . C3 . C4 . 120.07(18) yes C2 . C3 . H31 . 119.8 no C4 . C3 . H31 . 120.1 no C5 . C4 . C3 . 118.22(16) yes C5 . C4 . H41 . 120.7 no C3 . C4 . H41 . 121.0 no C6 . C7 . C8 . 123.08(16) yes C6 . C7 . H71 . 118.0 no C8 . C7 . H71 . 118.9 no C10 . C9 . C8 . 120.47(14) yes C10 . C9 . H91 . 119.2 no C8 . C9 . H91 . 120.3 no C15 . C14 . C13 . 120.53(15) yes C15 . C14 . H141 . 119.7 no C13 . C14 . H141 . 119.7 no C17 . C16 . C15 . 123.14(18) yes C17 . C16 . H161 . 118.6 no C15 . C16 . H161 . 118.2 no C18 . C19 . C20 . 118.70(16) yes C18 . C19 . H191 . 119.8 no C20 . C19 . H191 . 121.5 no C19 . C20 . C21 . 118.77(17) yes C19 . C20 . H201 . 120.4 no C21 . C20 . H201 . 120.8 no C20 . C21 . C22 . 119.52(16) yes C20 . C21 . H211 . 120.7 no C22 . C21 . H211 . 119.8 no C25 . C24 . C23 . 123.86(18) yes C25 . C24 . H241 . 118.7 no C23 . C24 . H241 . 117.4 no C27 . C26 . C25 . 120.73(16) yes C27 . C26 . H261 . 119.7 no C25 . C26 . H261 . 119.5 no C30 . C31 . C32 . 120.06(15) yes C30 . C31 . H311 . 119.9 no C32 . C31 . H311 . 120.1 no C32 . C33 . C34 . 124.25(18) yes C32 . C33 . H331 . 118.4 no C34 . C33 . H331 . 117.4 no C11 . N2 . C12 . 109.69(13) yes C11 . N2 . H1 . 124.9 no C12 . N2 . H1 . 125.4 no C28 . N4 . C29 . 108.81(13) yes C28 . N4 . H2 . 125.7 no C29 . N4 . H2 . 125.5 no C35 . C36 . H361 . 110.0 no C35 . C36 . H362 . 108.6 no H361 . C36 . H362 . 109.5 no C35 . C36 . H363 . 109.7 no H361 . C36 . H363 . 109.5 no H362 . C36 . H363 . 109.5 no C35 . C37 . H371 . 110.2 no C35 . C37 . H372 . 109.7 no H371 . C37 . H372 . 109.5 no C35 . C37 . H373 . 108.5 no H371 . C37 . H373 . 109.5 no H372 . C37 . H373 . 109.5 no C35 . C38 . H381 . 110.9 no C35 . C38 . H382 . 110.0 no H381 . C38 . H382 . 109.5 no C35 . C38 . H383 . 107.5 no H381 . C38 . H383 . 109.5 no H382 . C38 . H383 . 109.5 no C39 . C40 . H401 . 111.2 no C39 . C40 . H402 . 107.6 no H401 . C40 . H402 . 109.5 no C39 . C40 . H403 . 109.5 no H401 . C40 . H403 . 109.5 no H402 . C40 . H403 . 109.5 no C39 . C41 . H411 . 106.7 no C39 . C41 . H412 . 111.8 no H411 . C41 . H412 . 109.5 no C39 . C41 . H413 . 109.8 no H411 . C41 . H413 . 109.5 no H412 . C41 . H413 . 109.5 no C39 . C42 . H421 . 107.9 no C39 . C42 . H422 . 110.7 no H421 . C42 . H422 . 109.5 no C39 . C42 . H423 . 109.8 no H421 . C42 . H423 . 109.5 no H422 . C42 . H423 . 109.5 no C43 . C44 . H441 . 108.5 no C43 . C44 . H442 . 109.8 no H441 . C44 . H442 . 109.5 no C43 . C44 . H443 . 110.1 no H441 . C44 . H443 . 109.5 no H442 . C44 . H443 . 109.5 no C43 . C45 . H451 . 108.4 no C43 . C45 . H452 . 111.7 no H451 . C45 . H452 . 109.5 no C43 . C45 . H453 . 108.2 no H451 . C45 . H453 . 109.5 no H452 . C45 . H453 . 109.5 no C43 . C46 . H461 . 109.7 no C43 . C46 . H462 . 108.2 no H461 . C46 . H462 . 109.5 no C43 . C46 . H463 . 110.4 no H461 . C46 . H463 . 109.5 no H462 . C46 . H463 . 109.5 no C47 . C48 . H481 . 108.8 no C47 . C48 . H482 . 109.6 no H481 . C48 . H482 . 109.5 no C47 . C48 . H483 . 110.0 no H481 . C48 . H483 . 109.5 no H482 . C48 . H483 . 109.5 no C47 . C49 . H491 . 108.6 no C47 . C49 . H492 . 109.5 no H491 . C49 . H492 . 109.5 no C47 . C49 . H493 . 110.3 no H491 . C49 . H493 . 109.5 no H492 . C49 . H493 . 109.5 no C47 . C50 . H501 . 108.8 no C47 . C50 . H502 . 108.8 no H501 . C50 . H502 . 109.5 no C47 . C50 . H503 . 110.8 no H501 . C50 . H503 . 109.5 no H502 . C50 . H503 . 109.5 no C51 . O51 . C54 . 104.9(3) yes O51 . C51 . H511 . 103.5 no O51 . C51 . H512 . 110.8 no H511 . C51 . H512 . 109.5 no O51 . C51 . C52 . 115.0(4) yes H511 . C51 . C52 . 104.5 no H512 . C51 . C52 . 112.8 no C51 . C52 . H521 . 108.0 no C51 . C52 . H522 . 115.4 no H521 . C52 . H522 . 109.5 no C51 . C52 . C53 . 98.8(4) yes H521 . C52 . C53 . 113.0 no H522 . C52 . C53 . 111.8 no C52 . C53 . H531 . 110.8 no C52 . C53 . H532 . 110.6 no H531 . C53 . H532 . 109.5 no C52 . C53 . C54 . 106.1(5) yes H531 . C53 . C54 . 118.2 no H532 . C53 . C54 . 101.3 no O51 . C54 . C53 . 107.7(5) yes O51 . C54 . H541 . 115.2 no C53 . C54 . H541 . 116.8 no O51 . C54 . H542 . 103.3 no C53 . C54 . H542 . 102.8 no H541 . C54 . H542 . 109.5 no C61 2_566 O61 . C61 . 108.2(3) yes O61 . C61 . H611 . 123.0 no O61 . C61 . H612 . 123.6 no H611 . C61 . H612 . 109.5 no O61 . C61 . C62 . 107.9(3) yes H611 . C61 . C62 . 74.9 no H612 . C61 . C62 . 104.1 no O61 . C61 . C63 . 106.8(3) yes H611 . C61 . C63 . 103.7 no H612 . C61 . C63 . 77.0 no C62 . C61 . C63 . 34.5(4) yes C61 . C62 . C63 2_566 106.2(6) yes C61 . C62 . C62 2_566 94.3(4) yes C63 2_566 C62 . C62 2_566 30.6(5) yes C61 . C62 . H621 . 109.4 no C63 2_566 C62 . H621 . 110.4 no C62 2_566 C62 . H621 . 140.6 no C61 . C62 . H622 . 111.3 no C63 2_566 C62 . H622 . 110.0 no C62 2_566 C62 . H622 . 89.4 no H621 . C62 . H622 . 109.5 no C61 . C62 . C63 . 73.5(9) yes C63 2_566 C62 . C63 . 86.4(11) yes C62 2_566 C62 . C63 . 55.8(7) yes H621 . C62 . C63 . 160.4 no H622 . C62 . C63 . 53.4 no C61 . C62 . H631 . 125.2 no C63 2_566 C62 . H631 . 109.5 no C62 2_566 C62 . H631 . 96.0 no H621 . C62 . H631 . 95.4 no H622 . C62 . H631 . 16.2 no C63 . C62 . H631 . 68.8 no C62 . H622 . C63 . 59.3 no C61 . C63 . C62 2_566 107.4(6) yes C61 . C63 . C63 2_566 96.2(6) yes C62 2_566 C63 . C63 2_566 32.6(4) yes C61 . C63 . H622 . 119.1 no C62 2_566 C63 . H622 . 118.2 no C63 2_566 C63 . H622 . 101.2 no C61 . C63 . C62 . 72.0(9) yes C62 2_566 C63 . C62 . 93.6(10) yes C63 2_566 C63 . C62 . 61.0(10) yes H622 . C63 . C62 . 67.3 no C61 . C63 . H631 . 111.4 no C62 2_566 C63 . H631 . 110.3 no C63 2_566 C63 . H631 . 87.4 no H622 . C63 . H631 . 17.1 no C62 . C63 . H631 . 50.9 no C61 . C63 . H632 . 108.3 no C62 2_566 C63 . H632 . 109.9 no C63 2_566 C63 . H632 . 141.5 no H622 . C63 . H632 . 92.4 no C62 . C63 . H632 . 154.7 no H631 . C63 . H632 . 109.5 no C63 . H631 . C62 . 60.3 no O82 . O81 . C81 . 67.5(10) yes O82 . O81 . C84 . 54.8(10) yes C81 . O81 . C84 . 96.0(7) yes O81 . O82 . C81 . 56.7(8) yes O81 . O82 . C84 . 62.9(11) yes C81 . O82 . C84 . 94.1(13) yes O81 . C81 . O82 . 55.8(8) yes O81 . C81 . H811 . 78.0 no O82 . C81 . H811 . 133.8 no O81 . C81 . H812 . 125.3 no O82 . C81 . H812 . 106.1 no H811 . C81 . H812 . 98.6 no O81 . C81 . C82 . 109.9(7) yes O82 . C81 . C82 . 98.6(10) yes H811 . C81 . C82 . 98.8 no H812 . C81 . C82 . 124.3 no C81 . C82 . H821 . 97.1 no C81 . C82 . H822 . 119.8 no H821 . C82 . H822 . 96.9 no C81 . C82 . C83 . 106.5(7) yes H821 . C82 . C83 . 105.4 no H822 . C82 . C83 . 125.2 no C82 . C83 . H831 . 105.9 no C82 . C83 . H832 . 112.0 no H831 . C83 . H832 . 108.7 no C82 . C83 . C84 . 98.3(6) yes H831 . C83 . C84 . 116.9 no H832 . C83 . C84 . 114.3 no C83 . C84 . O81 . 105.2(6) yes C83 . C84 . O82 . 110.4(11) yes O81 . C84 . O82 . 62.3(10) yes C83 . C84 . H841 . 105.0 no O81 . C84 . H841 . 81.9 no O82 . C84 . H841 . 134.6 no C83 . C84 . H842 . 112.1 no O81 . C84 . H842 . 139.1 no O82 . C84 . H842 . 89.0 no H841 . C84 . H842 . 103.2 no C91 . O91 . C94 . 105.1(6) yes O91 . C91 . H911 . 111.9 no O91 . C91 . H912 . 105.9 no H911 . C91 . H912 . 117.7 no O91 . C91 . C92 . 114.8(6) yes H911 . C91 . C92 . 121.9 no H912 . C91 . C92 . 79.9 no C91 . C92 . H921 . 88.4 no C91 . C92 . H922 . 147.1 no H921 . C92 . H922 . 62.3 no C91 . C92 . C93 . 101.0(6) yes H921 . C92 . C93 . 79.8 no H922 . C92 . C93 . 88.8 no C92 . C93 . H931 . 138.6 no C92 . C93 . H932 . 95.9 no H931 . C93 . H932 . 105.9 no C92 . C93 . C94 . 108.9(7) yes H931 . C93 . C94 . 102.4 no H932 . C93 . C94 . 98.0 no C93 . C94 . O91 . 104.6(4) yes C93 . C94 . H941 . 115.4 no O91 . C94 . H941 . 108.7 no C93 . C94 . H942 . 109.3 no O91 . C94 . H942 . 106.4 no H941 . C94 . H942 . 111.8 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 N4 . H2 . O51 . 134 1.00 2.14 2.930(2) yes # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.322 0.884 0.233 101 19 ' ' 2 0.322 0.116 0.767 101 19 ' ' 3 0.678 0.384 0.267 101 19 ' ' 4 0.678 0.616 0.733 101 19 ' ' _platon_squeeze_details ; ;