# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 loop_ _publ_author_name _publ_author_address _publ_author_footnote E.Constable ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; H.-J.Guntherodt ; ? # Address 2 ; ; ? # Footnote 2 ; C.E.Housecroft '' '' 'Leo Merz' '' '' 'Markus Neuburger' '' '' ; S.Schaffner ; '' '' 'Yaqiu Tao.' '' '' _publ_contact_author_name 'Prof E. Constable' _publ_contact_author_address ; Departement Chemie University of Basel Spitalstrasse 51 Basel CH-4056 SWITZERLAND ; _publ_contact_author_email EDWIN.CONSTABLE@UNIBAS.CH _publ_section_title ; ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_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 285018' _publ_contact_author_phone '+44 1865 285024' # Check this file using the IUCr facility at: # http://journals.iucr.org/services/cif/checking/checkfull.html # 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 C. The figures have been sent by mail. ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' # Attachment '2.cif' data_yTao_c18PhTpy _database_code_depnum_ccdc_archive 'CCDC 274895' _audit_creation_date 04-09-29 _audit_creation_method CRYSTALS_ver_12.20 # 9270946 yTao_cisPhTpy_123k #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment mixed #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 6.45410(10) _cell_angle_alpha 98.7916(11) _cell_length_b 10.0694(2) _cell_angle_beta 93.2600(14) _cell_length_c 26.7131(6) _cell_angle_gamma 107.2415(13) _cell_volume 1628.93(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . 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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B _cell_formula_units_Z 2 _chemical_formula_sum ' C39 H51 N3 O1 ' _chemical_formula_moiety ' C39 H51 N3 O1 ' _chemical_compound_source ; ? ; _chemical_formula_weight 577.85 _cell_measurement_reflns_used 7635 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _cell_measurement_temperature 123 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colorless ' _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.070 _diffrn_measurement_device_type ; Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method '\f & \w scans' _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 1.00 # Sheldrick geometric definitions 0.99 1.00 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 123 _diffrn_reflns_number 15143 _reflns_number_total 7732 _diffrn_reflns_av_R_equivalents 0.02 # Number of reflections with Friedels Law is 7732 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7749 _diffrn_reflns_theta_min 3.105 _diffrn_reflns_theta_max 27.848 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.848 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 35 _refine_diff_density_min -0.20 _refine_diff_density_max 0.20 _refine_ls_number_reflns 3956 _refine_ls_number_restraints 0 _refine_ls_number_parameters 389 #_refine_ls_R_factor_ref 0.0399 _refine_ls_wR_factor_ref 0.0360 _refine_ls_goodness_of_fit_ref 1.1594 #_reflns_number_all 4661 _refine_ls_R_factor_all 0.0489 _refine_ls_wR_factor_all 0.0369 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 3956 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_gt 0.0360 _refine_ls_shift/su_max 0.000581 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.100E-01 0.00 0.00 0.00 0.00 0.333 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. 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 trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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 -0.35678(15) 0.09619(11) 0.77775(4) 0.0287 1.0000 Uani . . . . . . N1 N 0.96315(19) 0.68205(14) 0.83153(5) 0.0278 1.0000 Uani . . . . . . N2 N 0.95063(19) 0.43612(13) 0.91655(5) 0.0238 1.0000 Uani . . . . . . N3 N 0.73746(19) 0.16819(14) 0.99190(5) 0.0290 1.0000 Uani . . . . . . C1 C 1.1068(2) 0.79073(17) 0.81669(6) 0.0306 1.0000 Uani . . . . . . C2 C 1.3290(2) 0.83391(18) 0.83141(6) 0.0313 1.0000 Uani . . . . . . C3 C 1.4079(3) 0.75833(17) 0.86248(7) 0.0317 1.0000 Uani . . . . . . C4 C 1.2632(2) 0.64626(17) 0.87890(6) 0.0273 1.0000 Uani . . . . . . C5 C 1.0419(2) 0.61163(16) 0.86309(6) 0.0230 1.0000 Uani . . . . . . C6 C 0.8776(2) 0.49312(16) 0.87949(6) 0.0217 1.0000 Uani . . . . . . C7 C 0.6631(2) 0.44425(16) 0.85678(6) 0.0228 1.0000 Uani . . . . . . C8 C 0.5120(2) 0.33105(16) 0.87195(6) 0.0213 1.0000 Uani . . . . . . C9 C 0.5873(2) 0.27485(16) 0.91111(6) 0.0239 1.0000 Uani . . . . . . C10 C 0.8045(2) 0.32875(16) 0.93210(6) 0.0223 1.0000 Uani . . . . . . C11 C 0.8879(2) 0.26530(16) 0.97269(6) 0.0240 1.0000 Uani . . . . . . C12 C 1.1099(2) 0.30258(17) 0.98839(6) 0.0282 1.0000 Uani . . . . . . C13 C 1.1794(3) 0.23752(18) 1.02499(6) 0.0319 1.0000 Uani . . . . . . C14 C 1.0264(3) 0.13849(18) 1.04529(6) 0.0315 1.0000 Uani . . . . . . C15 C 0.8088(3) 0.10771(17) 1.02761(6) 0.0315 1.0000 Uani . . . . . . C16 C 0.2841(2) 0.27162(16) 0.84671(6) 0.0203 1.0000 Uani . . . . . . C17 C 0.2089(2) 0.32986(16) 0.80810(6) 0.0232 1.0000 Uani . . . . . . C18 C -0.0023(2) 0.27572(16) 0.78396(6) 0.0227 1.0000 Uani . . . . . . C19 C -0.1443(2) 0.15986(16) 0.79847(6) 0.0223 1.0000 Uani . . . . . . C20 C -0.0750(2) 0.09891(17) 0.83677(6) 0.0273 1.0000 Uani . . . . . . C21 C 0.1359(2) 0.15391(16) 0.86029(6) 0.0259 1.0000 Uani . . . . . . C22 C -0.4443(2) 0.15008(17) 0.73733(6) 0.0237 1.0000 Uani . . . . . . C23 C -0.6755(2) 0.05381(16) 0.72294(6) 0.0239 1.0000 Uani . . . . . . C24 C -0.7959(2) 0.08413(16) 0.67734(6) 0.0238 1.0000 Uani . . . . . . C25 C -1.0268(2) -0.01905(16) 0.66523(6) 0.0243 1.0000 Uani . . . . . . C26 C -1.1568(2) -0.00138(16) 0.61874(6) 0.0246 1.0000 Uani . . . . . . C27 C -1.3854(2) -0.10800(16) 0.60816(6) 0.0238 1.0000 Uani . . . . . . C28 C -1.5196(2) -0.09642(16) 0.56126(6) 0.0249 1.0000 Uani . . . . . . C29 C -1.7476(2) -0.20257(16) 0.55200(6) 0.0249 1.0000 Uani . . . . . . C30 C -1.8826(2) -0.19334(16) 0.50463(6) 0.0250 1.0000 Uani . . . . . . C31 C -2.1116(2) -0.29888(16) 0.49580(6) 0.0257 1.0000 Uani . . . . . . C32 C -2.2458(2) -0.28982(16) 0.44844(6) 0.0254 1.0000 Uani . . . . . . C33 C -2.4749(2) -0.39506(16) 0.43959(6) 0.0261 1.0000 Uani . . . . . . C34 C -2.6096(2) -0.38620(16) 0.39225(6) 0.0261 1.0000 Uani . . . . . . C35 C -2.8380(2) -0.49198(16) 0.38339(6) 0.0266 1.0000 Uani . . . . . . C36 C -2.9743(2) -0.48353(16) 0.33626(6) 0.0257 1.0000 Uani . . . . . . C37 C -3.2021(2) -0.58984(16) 0.32748(6) 0.0272 1.0000 Uani . . . . . . C38 C -3.3414(2) -0.57713(17) 0.28172(6) 0.0271 1.0000 Uani . . . . . . C39 C -3.5690(2) -0.68446(17) 0.27299(6) 0.0342 1.0000 Uani . . . . . . H11 H 1.0494(2) 0.84356(17) 0.79337(6) 0.0326 1.0000 Uiso R . . . . . H21 H 1.4288(2) 0.91804(18) 0.82012(6) 0.0357 1.0000 Uiso R . . . . . H31 H 1.5681(3) 0.78440(17) 0.87291(7) 0.0337 1.0000 Uiso R . . . . . H41 H 1.3168(2) 0.59034(17) 0.90160(6) 0.0300 1.0000 Uiso R . . . . . H71 H 0.6172(2) 0.49073(16) 0.82949(6) 0.0248 1.0000 Uiso R . . . . . H91 H 0.4852(2) 0.19541(16) 0.92437(6) 0.0275 1.0000 Uiso R . . . . . H121 H 1.2168(2) 0.37563(17) 0.97334(6) 0.0320 1.0000 Uiso R . . . . . H131 H 1.3382(3) 0.26138(18) 1.03658(6) 0.0356 1.0000 Uiso R . . . . . H141 H 1.0717(3) 0.09022(18) 1.07205(6) 0.0363 1.0000 Uiso R . . . . . H151 H 0.6976(3) 0.03649(17) 1.04244(6) 0.0369 1.0000 Uiso R . . . . . H171 H 0.3112(2) 0.41426(16) 0.79752(6) 0.0255 1.0000 Uiso R . . . . . H181 H -0.0512(2) 0.31946(16) 0.75617(6) 0.0269 1.0000 Uiso R . . . . . H201 H -0.1784(2) 0.01507(17) 0.84742(6) 0.0292 1.0000 Uiso R . . . . . H211 H 0.1847(2) 0.10842(16) 0.88754(6) 0.0293 1.0000 Uiso R . . . . . H221 H -0.4433(2) 0.24924(17) 0.74955(6) 0.0270 1.0000 Uiso R . . . . . H222 H -0.3579(2) 0.14764(17) 0.70748(6) 0.0270 1.0000 Uiso R . . . . . H231 H -0.7599(2) 0.06355(16) 0.75281(6) 0.0278 1.0000 Uiso R . . . . . H232 H -0.6715(2) -0.04560(16) 0.71467(6) 0.0278 1.0000 Uiso R . . . . . H241 H -0.8041(2) 0.18264(16) 0.68525(6) 0.0269 1.0000 Uiso R . . . . . H242 H -0.7135(2) 0.07481(16) 0.64707(6) 0.0269 1.0000 Uiso R . . . . . H251 H -1.1079(2) -0.00637(16) 0.69549(6) 0.0266 1.0000 Uiso R . . . . . H252 H -1.0155(2) -0.11703(16) 0.65920(6) 0.0266 1.0000 Uiso R . . . . . H261 H -1.1700(2) 0.09611(16) 0.62458(6) 0.0274 1.0000 Uiso R . . . . . H262 H -1.0769(2) -0.01409(16) 0.58826(6) 0.0274 1.0000 Uiso R . . . . . H271 H -1.4658(2) -0.09291(16) 0.63835(6) 0.0257 1.0000 Uiso R . . . . . H272 H -1.3710(2) -0.20520(16) 0.60365(6) 0.0257 1.0000 Uiso R . . . . . H281 H -1.5329(2) 0.00103(16) 0.56543(6) 0.0282 1.0000 Uiso R . . . . . H282 H -1.4411(2) -0.11314(16) 0.53087(6) 0.0282 1.0000 Uiso R . . . . . H291 H -1.8262(2) -0.18510(16) 0.58230(6) 0.0266 1.0000 Uiso R . . . . . H292 H -1.7339(2) -0.29986(16) 0.54825(6) 0.0266 1.0000 Uiso R . . . . . H301 H -1.8952(2) -0.09580(16) 0.50822(6) 0.0272 1.0000 Uiso R . . . . . H302 H -1.8048(2) -0.21173(16) 0.47427(6) 0.0272 1.0000 Uiso R . . . . . H311 H -2.1897(2) -0.28029(16) 0.52609(6) 0.0279 1.0000 Uiso R . . . . . H312 H -2.0990(2) -0.39642(16) 0.49232(6) 0.0279 1.0000 Uiso R . . . . . H321 H -2.2580(2) -0.19220(16) 0.45191(6) 0.0278 1.0000 Uiso R . . . . . H322 H -2.1676(2) -0.30850(16) 0.41816(6) 0.0278 1.0000 Uiso R . . . . . H331 H -2.5527(2) -0.37644(16) 0.46992(6) 0.0283 1.0000 Uiso R . . . . . H332 H -2.4624(2) -0.49264(16) 0.43608(6) 0.0283 1.0000 Uiso R . . . . . H341 H -2.6230(2) -0.28885(16) 0.39587(6) 0.0279 1.0000 Uiso R . . . . . H342 H -2.5312(2) -0.40410(16) 0.36195(6) 0.0279 1.0000 Uiso R . . . . . H351 H -2.9160(2) -0.47432(16) 0.41379(6) 0.0289 1.0000 Uiso R . . . . . H352 H -2.8245(2) -0.58930(16) 0.37963(6) 0.0289 1.0000 Uiso R . . . . . H361 H -2.9886(2) -0.38637(16) 0.33999(6) 0.0279 1.0000 Uiso R . . . . . H362 H -2.8966(2) -0.50111(16) 0.30580(6) 0.0279 1.0000 Uiso R . . . . . H371 H -3.2778(2) -0.57491(16) 0.35853(6) 0.0307 1.0000 Uiso R . . . . . H372 H -3.1882(2) -0.68717(16) 0.32227(6) 0.0307 1.0000 Uiso R . . . . . H381 H -3.3562(2) -0.48003(17) 0.28708(6) 0.0305 1.0000 Uiso R . . . . . H382 H -3.2650(2) -0.59123(17) 0.25074(6) 0.0305 1.0000 Uiso R . . . . . H391 H -3.6531(2) -0.67153(17) 0.24248(6) 0.0391 1.0000 Uiso R . . . . . H392 H -3.6470(2) -0.67077(17) 0.30372(6) 0.0391 1.0000 Uiso R . . . . . H393 H -3.5557(2) -0.78197(17) 0.26738(6) 0.0391 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 O1 0.0201(6) 0.0341(7) 0.0294(7) 0.0127(5) -0.0055(5) 0.0026(5) N1 0.0233(8) 0.0260(8) 0.0327(9) 0.0104(7) 0.0003(6) 0.0036(6) N2 0.0218(7) 0.0240(8) 0.0246(9) 0.0046(6) 0.0017(6) 0.0055(6) N3 0.0265(8) 0.0324(9) 0.0289(9) 0.0111(7) 0.0020(7) 0.0075(7) C1 0.0271(10) 0.0272(10) 0.0370(12) 0.0122(8) -0.0002(8) 0.0048(8) C2 0.0235(9) 0.0303(10) 0.0351(12) 0.0097(9) 0.0006(8) -0.0008(8) C3 0.0202(9) 0.0325(11) 0.0376(12) 0.0091(9) -0.0013(8) 0.0001(8) C4 0.0200(9) 0.0276(10) 0.0325(11) 0.0070(8) -0.0026(7) 0.0050(7) C5 0.0223(9) 0.0214(9) 0.0248(10) 0.0039(8) 0.0021(7) 0.0061(7) C6 0.0197(9) 0.0220(9) 0.0237(10) 0.0037(8) 0.0018(7) 0.0071(7) C7 0.0197(9) 0.0236(10) 0.0254(10) 0.0052(8) -0.0001(7) 0.0071(7) C8 0.0174(8) 0.0218(9) 0.0241(10) 0.0029(8) 0.0031(7) 0.0055(7) C9 0.0188(9) 0.0260(10) 0.0262(11) 0.0078(8) 0.0025(7) 0.0046(7) C10 0.0205(9) 0.0242(10) 0.0217(10) 0.0038(8) 0.0020(7) 0.0067(7) C11 0.0218(9) 0.0255(10) 0.0232(10) 0.0038(8) 0.0009(7) 0.0056(7) C12 0.0234(9) 0.0320(11) 0.0273(11) 0.0075(8) -0.0009(8) 0.0054(8) C13 0.0256(10) 0.0378(11) 0.0309(11) 0.0065(9) -0.0064(8) 0.0090(8) C14 0.0349(11) 0.0360(11) 0.0245(11) 0.0073(8) -0.0052(8) 0.0130(9) C15 0.0335(10) 0.0339(11) 0.0287(11) 0.0124(9) 0.0042(8) 0.0095(8) C16 0.0166(8) 0.0215(9) 0.0216(10) 0.0030(7) 0.0012(7) 0.0048(7) C17 0.0195(9) 0.0222(10) 0.0272(10) 0.0082(8) 0.0042(7) 0.0034(7) C18 0.0207(9) 0.0252(10) 0.0232(10) 0.0080(8) -0.0009(7) 0.0076(7) C19 0.0147(8) 0.0271(10) 0.0228(10) 0.0042(8) -0.0020(7) 0.0040(7) C20 0.0204(9) 0.0278(10) 0.0313(11) 0.0128(8) -0.0001(8) 0.0003(7) C21 0.0219(9) 0.0293(10) 0.0265(11) 0.0104(8) -0.0024(7) 0.0059(8) C22 0.0208(9) 0.0290(10) 0.0217(10) 0.0074(8) -0.0012(7) 0.0075(7) C23 0.0196(8) 0.0263(10) 0.0242(10) 0.0037(7) -0.0004(7) 0.0057(7) C24 0.0200(8) 0.0270(10) 0.0238(10) 0.0055(8) -0.0009(7) 0.0063(7) C25 0.0203(8) 0.0271(10) 0.0243(10) 0.0048(8) -0.0011(7) 0.0063(7) C26 0.0204(9) 0.0297(10) 0.0230(10) 0.0060(8) -0.0012(7) 0.0065(7) C27 0.0205(8) 0.0272(10) 0.0223(10) 0.0047(8) 0.0000(7) 0.0055(7) C28 0.0214(9) 0.0278(10) 0.0240(10) 0.0054(8) -0.0015(7) 0.0057(7) C29 0.0211(8) 0.0277(10) 0.0241(10) 0.0052(8) -0.0011(7) 0.0051(7) C30 0.0215(9) 0.0271(10) 0.0245(10) 0.0043(8) -0.0012(7) 0.0057(7) C31 0.0217(9) 0.0286(10) 0.0251(10) 0.0050(8) -0.0023(7) 0.0057(7) C32 0.0209(8) 0.0276(10) 0.0253(10) 0.0045(8) -0.0019(7) 0.0050(7) C33 0.0225(9) 0.0290(10) 0.0256(10) 0.0057(8) -0.0012(7) 0.0063(7) C34 0.0223(9) 0.0291(10) 0.0253(10) 0.0054(8) -0.0008(7) 0.0059(7) C35 0.0226(9) 0.0287(10) 0.0265(10) 0.0052(8) -0.0018(7) 0.0057(7) C36 0.0229(9) 0.0268(10) 0.0257(10) 0.0058(8) -0.0014(7) 0.0051(7) C37 0.0240(9) 0.0269(10) 0.0280(11) 0.0058(8) -0.0037(7) 0.0046(7) C38 0.0243(9) 0.0306(10) 0.0252(10) 0.0052(8) -0.0029(7) 0.0077(7) C39 0.0268(9) 0.0406(11) 0.0332(11) 0.0082(9) -0.0052(8) 0.0083(8) _refine_ls_extinction_coef 130(10) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' 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 . C19 . 1.3721(15) yes O1 . C22 . 1.4388(17) yes N1 . C1 . 1.3368(18) yes N1 . C5 . 1.3491(18) yes N2 . C6 . 1.3464(18) yes N2 . C10 . 1.3447(18) yes N3 . C11 . 1.3453(19) yes N3 . C15 . 1.3366(19) yes C1 . C2 . 1.3839(19) yes C1 . H11 . 1.000 no C2 . C3 . 1.379(2) yes C2 . H21 . 1.000 no C3 . C4 . 1.382(2) yes C3 . H31 . 1.000 no C4 . C5 . 1.3896(19) yes C4 . H41 . 1.000 no C5 . C6 . 1.484(2) yes C6 . C7 . 1.3915(19) yes C7 . C8 . 1.393(2) yes C7 . H71 . 1.000 no C8 . C9 . 1.391(2) yes C8 . C16 . 1.4896(19) yes C9 . C10 . 1.3930(19) yes C9 . H91 . 1.000 no C10 . C11 . 1.491(2) yes C11 . C12 . 1.391(2) yes C12 . C13 . 1.381(2) yes C12 . H121 . 1.000 no C13 . C14 . 1.381(2) yes C13 . H131 . 1.000 no C14 . C15 . 1.3829(19) yes C14 . H141 . 1.000 no C15 . H151 . 1.000 no C16 . C17 . 1.393(2) yes C16 . C21 . 1.397(2) yes C17 . C18 . 1.3870(19) yes C17 . H171 . 1.000 no C18 . C19 . 1.377(2) yes C18 . H181 . 1.000 no C19 . C20 . 1.388(2) yes C20 . C21 . 1.3794(19) yes C20 . H201 . 1.000 no C21 . H211 . 1.000 no C22 . C23 . 1.5095(18) yes C22 . H221 . 1.000 no C22 . H222 . 1.000 no C23 . C24 . 1.525(2) yes C23 . H231 . 1.000 no C23 . H232 . 1.000 no C24 . C25 . 1.5267(18) yes C24 . H241 . 1.000 no C24 . H242 . 1.000 no C25 . C26 . 1.5215(19) yes C25 . H251 . 1.000 no C25 . H252 . 1.000 no C26 . C27 . 1.5264(18) yes C26 . H261 . 1.000 no C26 . H262 . 1.000 no C27 . C28 . 1.5216(19) yes C27 . H271 . 1.000 no C27 . H272 . 1.000 no C28 . C29 . 1.5210(18) yes C28 . H281 . 1.000 no C28 . H282 . 1.000 no C29 . C30 . 1.5257(19) yes C29 . H291 . 1.000 no C29 . H292 . 1.000 no C30 . C31 . 1.5236(19) yes C30 . H301 . 1.000 no C30 . H302 . 1.000 no C31 . C32 . 1.5220(19) yes C31 . H311 . 1.000 no C31 . H312 . 1.000 no C32 . C33 . 1.5232(18) yes C32 . H321 . 1.000 no C32 . H322 . 1.000 no C33 . C34 . 1.5227(19) yes C33 . H331 . 1.000 no C33 . H332 . 1.000 no C34 . C35 . 1.5220(18) yes C34 . H341 . 1.000 no C34 . H342 . 1.000 no C35 . C36 . 1.5222(19) yes C35 . H351 . 1.000 no C35 . H352 . 1.000 no C36 . C37 . 1.5209(19) yes C36 . H361 . 1.000 no C36 . H362 . 1.000 no C37 . C38 . 1.5198(19) yes C37 . H371 . 1.000 no C37 . H372 . 1.000 no C38 . C39 . 1.5242(19) yes C38 . H381 . 1.000 no C38 . H382 . 1.000 no C39 . H391 . 1.000 no C39 . H392 . 1.000 no C39 . H393 . 1.000 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 C19 . O1 . C22 . 119.62(12) yes C1 . N1 . C5 . 117.25(13) yes C6 . N2 . C10 . 116.91(13) yes C11 . N3 . C15 . 117.35(13) yes N1 . C1 . C2 . 124.09(16) yes N1 . C1 . H11 . 117.668 no C2 . C1 . H11 . 118.237 no C1 . C2 . C3 . 117.97(16) yes C1 . C2 . H21 . 120.840 no C3 . C2 . H21 . 121.188 no C2 . C3 . C4 . 119.31(15) yes C2 . C3 . H31 . 120.204 no C4 . C3 . H31 . 120.490 no C3 . C4 . C5 . 118.99(15) yes C3 . C4 . H41 . 120.640 no C5 . C4 . H41 . 120.366 no C4 . C5 . N1 . 122.34(15) yes C4 . C5 . C6 . 121.83(15) yes N1 . C5 . C6 . 115.82(13) yes C5 . C6 . N2 . 115.86(13) yes C5 . C6 . C7 . 121.07(15) yes N2 . C6 . C7 . 123.07(15) yes C6 . C7 . C8 . 120.28(15) yes C6 . C7 . H71 . 119.809 no C8 . C7 . H71 . 119.915 no C7 . C8 . C9 . 116.35(14) yes C7 . C8 . C16 . 121.64(14) yes C9 . C8 . C16 . 122.00(14) yes C8 . C9 . C10 . 120.36(15) yes C8 . C9 . H91 . 120.015 no C10 . C9 . H91 . 119.624 no C9 . C10 . N2 . 123.00(15) yes C9 . C10 . C11 . 120.55(15) yes N2 . C10 . C11 . 116.42(13) yes C10 . C11 . N3 . 116.25(13) yes C10 . C11 . C12 . 121.25(15) yes N3 . C11 . C12 . 122.48(15) yes C11 . C12 . C13 . 119.00(16) yes C11 . C12 . H121 . 120.163 no C13 . C12 . H121 . 120.835 no C12 . C13 . C14 . 119.05(15) yes C12 . C13 . H131 . 120.589 no C14 . C13 . H131 . 120.365 no C13 . C14 . C15 . 118.28(16) yes C13 . C14 . H141 . 120.852 no C15 . C14 . H141 . 120.867 no C14 . C15 . N3 . 123.84(16) yes C14 . C15 . H151 . 118.397 no N3 . C15 . H151 . 117.760 no C8 . C16 . C17 . 121.69(14) yes C8 . C16 . C21 . 121.60(14) yes C17 . C16 . C21 . 116.71(13) yes C16 . C17 . C18 . 122.57(15) yes C16 . C17 . H171 . 118.611 no C18 . C17 . H171 . 118.816 no C17 . C18 . C19 . 119.11(15) yes C17 . C18 . H181 . 120.707 no C19 . C18 . H181 . 120.185 no C18 . C19 . O1 . 124.94(14) yes C18 . C19 . C20 . 119.93(13) yes O1 . C19 . C20 . 115.13(14) yes C19 . C20 . C21 . 120.20(15) yes C19 . C20 . H201 . 119.889 no C21 . C20 . H201 . 119.910 no C16 . C21 . C20 . 121.47(15) yes C16 . C21 . H211 . 118.983 no C20 . C21 . H211 . 119.542 no O1 . C22 . C23 . 105.43(12) yes O1 . C22 . H221 . 110.361 no C23 . C22 . H221 . 110.324 no O1 . C22 . H222 . 110.757 no C23 . C22 . H222 . 110.446 no H221 . C22 . H222 . 109.467 no C22 . C23 . C24 . 114.66(13) yes C22 . C23 . H231 . 108.435 no C24 . C23 . H231 . 107.915 no C22 . C23 . H232 . 108.196 no C24 . C23 . H232 . 108.091 no H231 . C23 . H232 . 109.467 no C23 . C24 . C25 . 111.00(12) yes C23 . C24 . H241 . 109.149 no C25 . C24 . H241 . 109.042 no C23 . C24 . H242 . 108.947 no C25 . C24 . H242 . 109.221 no H241 . C24 . H242 . 109.467 no C24 . C25 . C26 . 114.91(12) yes C24 . C25 . H251 . 108.121 no C26 . C25 . H251 . 108.359 no C24 . C25 . H252 . 107.861 no C26 . C25 . H252 . 108.039 no H251 . C25 . H252 . 109.466 no C25 . C26 . C27 . 112.65(12) yes C25 . C26 . H261 . 108.575 no C27 . C26 . H261 . 108.729 no C25 . C26 . H262 . 108.891 no C27 . C26 . H262 . 108.491 no H261 . C26 . H262 . 109.467 no C26 . C27 . C28 . 114.50(12) yes C26 . C27 . H271 . 108.107 no C28 . C27 . H271 . 107.918 no C26 . C27 . H272 . 108.286 no C28 . C27 . H272 . 108.495 no H271 . C27 . H272 . 109.467 no C27 . C28 . C29 . 113.41(12) yes C27 . C28 . H281 . 108.762 no C29 . C28 . H281 . 108.652 no C27 . C28 . H282 . 108.210 no C29 . C28 . H282 . 108.292 no H281 . C28 . H282 . 109.467 no C28 . C29 . C30 . 113.87(12) yes C28 . C29 . H291 . 108.144 no C30 . C29 . H291 . 108.337 no C28 . C29 . H292 . 108.485 no C30 . C29 . H292 . 108.481 no H291 . C29 . H292 . 109.467 no C29 . C30 . C31 . 113.68(12) yes C29 . C30 . H301 . 108.510 no C31 . C30 . H301 . 108.508 no C29 . C30 . H302 . 108.381 no C31 . C30 . H302 . 108.241 no H301 . C30 . H302 . 109.467 no C30 . C31 . C32 . 113.60(12) yes C30 . C31 . H311 . 108.271 no C32 . C31 . H311 . 108.371 no C30 . C31 . H312 . 108.531 no C32 . C31 . H312 . 108.547 no H311 . C31 . H312 . 109.467 no C31 . C32 . C33 . 113.69(12) yes C31 . C32 . H321 . 108.496 no C33 . C32 . H321 . 108.513 no C31 . C32 . H322 . 108.322 no C33 . C32 . H322 . 108.302 no H321 . C32 . H322 . 109.467 no C32 . C33 . C34 . 113.82(12) yes C32 . C33 . H331 . 108.232 no C34 . C33 . H331 . 108.372 no C32 . C33 . H332 . 108.445 no C34 . C33 . H332 . 108.450 no H331 . C33 . H332 . 109.467 no C33 . C34 . C35 . 113.68(12) yes C33 . C34 . H341 . 108.462 no C35 . C34 . H341 . 108.390 no C33 . C34 . H342 . 108.374 no C35 . C34 . H342 . 108.416 no H341 . C34 . H342 . 109.467 no C34 . C35 . C36 . 114.06(12) yes C34 . C35 . H351 . 108.349 no C36 . C35 . H351 . 108.275 no C34 . C35 . H352 . 108.330 no C36 . C35 . H352 . 108.297 no H351 . C35 . H352 . 109.467 no C35 . C36 . C37 . 113.83(12) yes C35 . C36 . H361 . 108.437 no C37 . C36 . H361 . 108.397 no C35 . C36 . H362 . 108.412 no C37 . C36 . H362 . 108.246 no H361 . C36 . H362 . 109.467 no C36 . C37 . C38 . 113.77(13) yes C36 . C37 . H371 . 108.276 no C38 . C37 . H371 . 108.285 no C36 . C37 . H372 . 108.505 no C38 . C37 . H372 . 108.481 no H371 . C37 . H372 . 109.467 no C37 . C38 . C39 . 113.49(13) yes C37 . C38 . H381 . 108.446 no C39 . C38 . H381 . 108.558 no C37 . C38 . H382 . 108.235 no C39 . C38 . H382 . 108.595 no H381 . C38 . H382 . 109.467 no C38 . C39 . H391 . 110.118 no C38 . C39 . H392 . 109.159 no H391 . C39 . H392 . 109.476 no C38 . C39 . H393 . 109.121 no H391 . C39 . H393 . 109.476 no H392 . C39 . H393 . 109.476 no # Attachment '3.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 274896' _audit_creation_date 05-02-28 _audit_creation_method CRYSTALS_ver_12.24 _oxford_structure_analysis_title '2280943 yTao_C8_oph_tpy_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.4461(3) _cell_length_b 10.3457(5) _cell_length_c 18.8455(8) _cell_angle_alpha 83.808(3) _cell_angle_beta 86.289(3) _cell_angle_gamma 72.097(2) _cell_volume 1188.30(10) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 _chemical_formula_sum 'C29 H31 N3 O1' _chemical_formula_moiety 'C29 H31 N3 O1' _chemical_compound_source ? _chemical_formula_weight 437.58 _cell_measurement_reflns_used 5382 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.28 _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 # Sheldrick geometric definitions 0.99 0.99 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _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 10656 _reflns_number_total 5475 _diffrn_reflns_av_R_equivalents 0.025 # Number of reflections with Friedels Law is 5475 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5486 _diffrn_reflns_theta_min 2.078 _diffrn_reflns_theta_max 27.551 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.551 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _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 -0.33 _refine_diff_density_max 0.29 _refine_ls_number_reflns 3247 _refine_ls_number_restraints 0 _refine_ls_number_parameters 298 #_refine_ls_R_factor_ref 0.0438 _refine_ls_wR_factor_ref 0.0529 _refine_ls_goodness_of_fit_ref 1.1280 #_reflns_number_all 5421 _refine_ls_R_factor_all 0.0725 _refine_ls_wR_factor_all 0.0965 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3247 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_gt 0.0529 _refine_ls_shift/su_max 0.000398 # 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: 0.644 0.580 0.240 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; # 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) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, (1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., 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 atoms attached 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 0.19697(17) 0.24793(11) 0.30759(6) 0.0418 1.0000 Uani . . . . . . N1 N 1.2382(2) 0.32772(14) 0.01295(7) 0.0430 1.0000 Uani . . . . . . N2 N 1.4679(2) 0.00577(13) 0.11545(7) 0.0342 1.0000 Uani . . . . . . N3 N 1.4999(2) -0.29794(14) 0.23225(7) 0.0405 1.0000 Uani . . . . . . C1 C 1.3012(3) 0.41261(18) -0.03626(9) 0.0467 1.0000 Uani . . . . . . C2 C 1.5143(3) 0.39102(19) -0.06107(9) 0.0475 1.0000 Uani . . . . . . C3 C 1.6716(3) 0.27636(19) -0.03418(9) 0.0466 1.0000 Uani . . . . . . C4 C 1.6099(3) 0.18567(18) 0.01612(8) 0.0421 1.0000 Uani . . . . . . C5 C 1.3922(2) 0.21522(16) 0.03857(8) 0.0353 1.0000 Uani . . . . . . C6 C 1.3187(2) 0.12386(15) 0.09433(8) 0.0328 1.0000 Uani . . . . . . C7 C 1.1068(2) 0.16380(16) 0.12315(8) 0.0351 1.0000 Uani . . . . . . C8 C 1.0403(2) 0.08009(15) 0.17718(8) 0.0319 1.0000 Uani . . . . . . C9 C 1.1955(2) -0.04371(15) 0.19793(8) 0.0340 1.0000 Uani . . . . . . C10 C 1.4039(2) -0.07665(15) 0.16645(8) 0.0323 1.0000 Uani . . . . . . C11 C 1.5710(2) -0.20679(16) 0.18928(8) 0.0343 1.0000 Uani . . . . . . C12 C 1.7898(3) -0.23163(17) 0.16786(9) 0.0416 1.0000 Uani . . . . . . C13 C 1.9380(3) -0.35502(18) 0.19035(10) 0.0479 1.0000 Uani . . . . . . C14 C 1.8655(3) -0.45107(18) 0.23256(9) 0.0468 1.0000 Uani . . . . . . C15 C 1.6461(3) -0.41703(17) 0.25266(9) 0.0449 1.0000 Uani . . . . . . C16 C 0.8199(2) 0.12192(15) 0.21173(7) 0.0309 1.0000 Uani . . . . . . C17 C 0.6687(2) 0.24838(16) 0.19317(8) 0.0380 1.0000 Uani . . . . . . C18 C 0.4639(3) 0.28692(17) 0.22577(9) 0.0404 1.0000 Uani . . . . . . C19 C 0.4030(2) 0.19959(15) 0.27866(8) 0.0343 1.0000 Uani . . . . . . C20 C 0.5496(2) 0.07418(15) 0.29858(8) 0.0346 1.0000 Uani . . . . . . C21 C 0.7547(2) 0.03673(15) 0.26517(8) 0.0350 1.0000 Uani . . . . . . C22 C 0.1222(2) 0.16614(16) 0.36354(8) 0.0366 1.0000 Uani . . . . . . C23 C -0.1062(2) 0.25062(17) 0.38433(8) 0.0375 1.0000 Uani . . . . . . C24 C -0.2099(3) 0.18554(17) 0.44740(8) 0.0389 1.0000 Uani . . . . . . C25 C -0.4371(3) 0.27770(17) 0.46576(8) 0.0393 1.0000 Uani . . . . . . C26 C -0.5521(3) 0.22424(17) 0.53015(8) 0.0404 1.0000 Uani . . . . . . C27 C -0.7768(3) 0.32296(17) 0.54634(8) 0.0415 1.0000 Uani . . . . . . C28 C -0.9006(3) 0.27187(18) 0.60923(8) 0.0421 1.0000 Uani . . . . . . C29 C -1.1260(3) 0.3708(2) 0.62262(10) 0.0515 1.0000 Uani . . . . . . H11 H 1.1895 0.4963 -0.0540 0.0487 1.0000 Uiso R . . . . . H21 H 1.5490 0.4560 -0.0987 0.0519 1.0000 Uiso R . . . . . H31 H 1.8267 0.2587 -0.0487 0.0521 1.0000 Uiso R . . . . . H41 H 1.7194 0.1008 0.0360 0.0438 1.0000 Uiso R . . . . . H71 H 1.0028 0.2513 0.1046 0.0361 1.0000 Uiso R . . . . . H91 H 1.1555 -0.1079 0.2335 0.0347 1.0000 Uiso R . . . . . H121 H 1.8343 -0.1637 0.1352 0.0429 1.0000 Uiso R . . . . . H131 H 2.0954 -0.3721 0.1798 0.0489 1.0000 Uiso R . . . . . H141 H 1.9665 -0.5395 0.2489 0.0459 1.0000 Uiso R . . . . . H151 H 1.5987 -0.4816 0.2875 0.0460 1.0000 Uiso R . . . . . H171 H 0.7054 0.3109 0.1543 0.0389 1.0000 Uiso R . . . . . H181 H 0.3560 0.3747 0.2091 0.0402 1.0000 Uiso R . . . . . H201 H 0.5122 0.0121 0.3373 0.0347 1.0000 Uiso R . . . . . H211 H 0.8589 -0.0504 0.2813 0.0348 1.0000 Uiso R . . . . . H221 H 0.2201 0.1456 0.4055 0.0386 1.0000 Uiso R . . . . . H222 H 0.1198 0.0800 0.3456 0.0393 1.0000 Uiso R . . . . . H231 H -0.0997 0.3395 0.3965 0.0402 1.0000 Uiso R . . . . . H232 H -0.2003 0.2654 0.3423 0.0400 1.0000 Uiso R . . . . . H241 H -0.1175 0.1720 0.4903 0.0408 1.0000 Uiso R . . . . . H242 H -0.2185 0.0976 0.4368 0.0413 1.0000 Uiso R . . . . . H251 H -0.4241 0.3651 0.4749 0.0421 1.0000 Uiso R . . . . . H252 H -0.5297 0.2923 0.4233 0.0418 1.0000 Uiso R . . . . . H261 H -0.4594 0.2087 0.5726 0.0428 1.0000 Uiso R . . . . . H262 H -0.5699 0.1376 0.5216 0.0432 1.0000 Uiso R . . . . . H271 H -0.8654 0.3374 0.5023 0.0439 1.0000 Uiso R . . . . . H272 H -0.7595 0.4094 0.5558 0.0445 1.0000 Uiso R . . . . . H281 H -0.8137 0.2577 0.6533 0.0460 1.0000 Uiso R . . . . . H282 H -0.9170 0.1841 0.5988 0.0463 1.0000 Uiso R . . . . . H291 H -1.2178 0.3865 0.5800 0.0560 1.0000 Uiso R . . . . . H292 H -1.1191 0.4609 0.6323 0.0562 1.0000 Uiso R . . . . . H293 H -1.2074 0.3398 0.6629 0.0562 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 O1 0.0293(6) 0.0431(6) 0.0449(6) 0.0077(5) 0.0085(5) -0.0049(5) N1 0.0384(8) 0.0440(8) 0.0434(7) 0.0074(6) 0.0019(6) -0.0122(6) N2 0.0287(6) 0.0372(7) 0.0356(6) -0.0012(5) 0.0026(5) -0.0096(5) N3 0.0330(7) 0.0368(7) 0.0477(7) 0.0049(6) 0.0036(6) -0.0084(6) C1 0.0496(10) 0.0427(9) 0.0439(9) 0.0086(7) -0.0002(7) -0.0127(8) C2 0.0533(11) 0.0514(10) 0.0387(9) 0.0040(7) 0.0077(7) -0.0218(9) C3 0.0412(9) 0.0541(10) 0.0426(9) 0.0011(8) 0.0117(7) -0.0162(8) C4 0.0358(8) 0.0484(10) 0.0389(8) 0.0024(7) 0.0051(6) -0.0115(7) C5 0.0338(8) 0.0389(8) 0.0323(7) -0.0006(6) 0.0025(6) -0.0115(7) C6 0.0296(7) 0.0354(8) 0.0327(7) 0.0004(6) 0.0006(6) -0.0102(6) C7 0.0302(8) 0.0360(8) 0.0364(8) 0.0037(6) 0.0003(6) -0.0085(6) C8 0.0268(7) 0.0350(8) 0.0337(7) -0.0011(6) -0.0005(6) -0.0098(6) C9 0.0306(8) 0.0357(8) 0.0354(8) 0.0013(6) 0.0018(6) -0.0116(6) C10 0.0281(7) 0.0325(8) 0.0356(7) -0.0016(6) 0.0012(6) -0.0093(6) C11 0.0294(7) 0.0358(8) 0.0361(8) -0.0022(6) 0.0035(6) -0.0089(6) C12 0.0336(8) 0.0395(9) 0.0464(9) 0.0028(7) 0.0069(7) -0.0072(7) C13 0.0309(8) 0.0485(10) 0.0547(10) 0.0032(8) 0.0062(7) -0.0020(7) C14 0.0377(9) 0.0386(9) 0.0531(10) 0.0063(7) 0.0029(7) 0.0000(7) C15 0.0393(9) 0.0366(9) 0.0523(10) 0.0067(7) 0.0041(7) -0.0068(7) C16 0.0250(7) 0.0341(8) 0.0323(7) -0.0004(6) 0.0003(5) -0.0082(6) C17 0.0321(8) 0.0375(8) 0.0396(8) 0.0071(6) 0.0035(6) -0.0083(6) C18 0.0312(8) 0.0374(8) 0.0446(9) 0.0079(7) 0.0034(6) -0.0033(6) C19 0.0255(7) 0.0394(8) 0.0355(7) -0.0015(6) 0.0028(6) -0.0076(6) C20 0.0309(8) 0.0356(8) 0.0353(7) 0.0039(6) 0.0034(6) -0.0105(6) C21 0.0280(7) 0.0344(8) 0.0387(8) 0.0035(6) 0.0009(6) -0.0064(6) C22 0.0315(8) 0.0426(9) 0.0344(7) 0.0009(6) 0.0044(6) -0.0119(7) C23 0.0304(8) 0.0447(9) 0.0364(8) -0.0017(7) 0.0049(6) -0.0116(7) C24 0.0335(8) 0.0437(9) 0.0374(8) -0.0003(7) 0.0045(6) -0.0110(7) C25 0.0356(8) 0.0442(9) 0.0368(8) -0.0008(7) 0.0056(6) -0.0122(7) C26 0.0368(9) 0.0457(9) 0.0375(8) 0.0008(7) 0.0063(6) -0.0137(7) C27 0.0397(9) 0.0441(9) 0.0377(8) 0.0003(7) 0.0083(7) -0.0118(7) C28 0.0378(9) 0.0492(10) 0.0382(8) 0.0004(7) 0.0073(7) -0.0149(7) C29 0.0405(9) 0.0630(12) 0.0475(9) -0.0014(8) 0.0113(7) -0.0143(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.8790(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C19 . 1.3670(17) yes O1 . C22 . 1.4326(17) yes N1 . C1 . 1.338(2) yes N1 . C5 . 1.343(2) yes N2 . C6 . 1.3409(19) yes N2 . C10 . 1.3449(18) yes N3 . C11 . 1.3445(19) yes N3 . C15 . 1.336(2) yes C1 . C2 . 1.380(2) yes C1 . H11 . 0.983 no C2 . C3 . 1.375(3) yes C2 . H21 . 0.988 no C3 . C4 . 1.388(2) yes C3 . H31 . 0.985 no C4 . C5 . 1.389(2) yes C4 . H41 . 0.996 no C5 . C6 . 1.489(2) yes C6 . C7 . 1.392(2) yes C7 . C8 . 1.397(2) yes C7 . H71 . 0.990 no C8 . C9 . 1.396(2) yes C8 . C16 . 1.4806(19) yes C9 . C10 . 1.390(2) yes C9 . H91 . 0.972 no C10 . C11 . 1.484(2) yes C11 . C12 . 1.394(2) yes C12 . C13 . 1.381(2) yes C12 . H121 . 0.981 no C13 . C14 . 1.380(2) yes C13 . H131 . 0.986 no C14 . C15 . 1.386(2) yes C14 . H141 . 0.977 no C15 . H151 . 0.988 no C16 . C17 . 1.395(2) yes C16 . C21 . 1.396(2) yes C17 . C18 . 1.380(2) yes C17 . H171 . 0.990 no C18 . C19 . 1.392(2) yes C18 . H181 . 0.993 no C19 . C20 . 1.380(2) yes C20 . C21 . 1.387(2) yes C20 . H201 . 0.988 no C21 . H211 . 0.975 no C22 . C23 . 1.514(2) yes C22 . H221 . 1.006 no C22 . H222 . 0.991 no C23 . C24 . 1.521(2) yes C23 . H231 . 0.986 no C23 . H232 . 0.999 no C24 . C25 . 1.524(2) yes C24 . H241 . 1.008 no C24 . H242 . 0.971 no C25 . C26 . 1.523(2) yes C25 . H251 . 0.968 no C25 . H252 . 1.000 no C26 . C27 . 1.528(2) yes C26 . H261 . 0.998 no C26 . H262 . 0.969 no C27 . C28 . 1.524(2) yes C27 . H271 . 1.009 no C27 . H272 . 0.971 no C28 . C29 . 1.522(2) yes C28 . H281 . 1.004 no C28 . H282 . 0.987 no C29 . H291 . 0.998 no C29 . H292 . 0.984 no C29 . H293 . 0.976 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 C19 . O1 . C22 . 119.45(12) yes C1 . N1 . C5 . 117.44(14) yes C6 . N2 . C10 . 116.92(12) yes C11 . N3 . C15 . 117.64(13) yes N1 . C1 . C2 . 123.58(16) yes N1 . C1 . H11 . 117.504 no C2 . C1 . H11 . 118.878 no C1 . C2 . C3 . 118.74(15) yes C1 . C2 . H21 . 119.493 no C3 . C2 . H21 . 121.731 no C2 . C3 . C4 . 118.81(15) yes C2 . C3 . H31 . 121.592 no C4 . C3 . H31 . 119.570 no C3 . C4 . C5 . 118.88(15) yes C3 . C4 . H41 . 120.845 no C5 . C4 . H41 . 120.274 no C4 . C5 . N1 . 122.54(14) yes C4 . C5 . C6 . 121.04(14) yes N1 . C5 . C6 . 116.41(13) yes C5 . C6 . N2 . 116.47(13) yes C5 . C6 . C7 . 120.30(13) yes N2 . C6 . C7 . 123.21(13) yes C6 . C7 . C8 . 120.25(14) yes C6 . C7 . H71 . 119.547 no C8 . C7 . H71 . 120.196 no C7 . C8 . C9 . 116.12(13) yes C7 . C8 . C16 . 121.91(13) yes C9 . C8 . C16 . 121.95(13) yes C8 . C9 . C10 . 120.26(13) yes C8 . C9 . H91 . 119.521 no C10 . C9 . H91 . 120.196 no C9 . C10 . N2 . 123.22(14) yes C9 . C10 . C11 . 120.54(13) yes N2 . C10 . C11 . 116.23(12) yes C10 . C11 . N3 . 116.32(13) yes C10 . C11 . C12 . 121.48(13) yes N3 . C11 . C12 . 122.19(14) yes C11 . C12 . C13 . 118.97(15) yes C11 . C12 . H121 . 119.663 no C13 . C12 . H121 . 121.283 no C12 . C13 . C14 . 119.29(15) yes C12 . C13 . H131 . 120.748 no C14 . C13 . H131 . 119.778 no C13 . C14 . C15 . 118.02(15) yes C13 . C14 . H141 . 121.032 no C15 . C14 . H141 . 120.933 no C14 . C15 . N3 . 123.84(15) yes C14 . C15 . H151 . 117.562 no N3 . C15 . H151 . 118.364 no C8 . C16 . C17 . 121.81(13) yes C8 . C16 . C21 . 121.35(13) yes C17 . C16 . C21 . 116.84(13) yes C16 . C17 . C18 . 121.51(14) yes C16 . C17 . H171 . 119.813 no C18 . C17 . H171 . 118.621 no C17 . C18 . C19 . 120.37(14) yes C17 . C18 . H181 . 119.697 no C19 . C18 . H181 . 119.798 no C18 . C19 . O1 . 115.62(13) yes C18 . C19 . C20 . 119.49(13) yes O1 . C19 . C20 . 124.89(13) yes C19 . C20 . C21 . 119.46(13) yes C19 . C20 . H201 . 120.931 no C21 . C20 . H201 . 119.579 no C16 . C21 . C20 . 122.32(14) yes C16 . C21 . H211 . 119.043 no C20 . C21 . H211 . 118.572 no O1 . C22 . C23 . 105.71(12) yes O1 . C22 . H221 . 110.238 no C23 . C22 . H221 . 110.479 no O1 . C22 . H222 . 109.723 no C23 . C22 . H222 . 110.571 no H221 . C22 . H222 . 110.042 no C22 . C23 . C24 . 114.07(13) yes C22 . C23 . H231 . 108.260 no C24 . C23 . H231 . 108.542 no C22 . C23 . H232 . 108.352 no C24 . C23 . H232 . 108.411 no H231 . C23 . H232 . 109.119 no C23 . C24 . C25 . 110.85(13) yes C23 . C24 . H241 . 108.945 no C25 . C24 . H241 . 107.947 no C23 . C24 . H242 . 110.324 no C25 . C24 . H242 . 109.678 no H241 . C24 . H242 . 109.036 no C24 . C25 . C26 . 115.06(13) yes C24 . C25 . H251 . 107.894 no C26 . C25 . H251 . 108.474 no C24 . C25 . H252 . 108.538 no C26 . C25 . H252 . 108.648 no H251 . C25 . H252 . 108.026 no C25 . C26 . C27 . 112.21(13) yes C25 . C26 . H261 . 108.850 no C27 . C26 . H261 . 109.420 no C25 . C26 . H262 . 109.789 no C27 . C26 . H262 . 108.510 no H261 . C26 . H262 . 107.968 no C26 . C27 . C28 . 114.04(13) yes C26 . C27 . H271 . 107.396 no C28 . C27 . H271 . 108.373 no C26 . C27 . H272 . 108.787 no C28 . C27 . H272 . 109.115 no H271 . C27 . H272 . 109.029 no C27 . C28 . C29 . 112.70(14) yes C27 . C28 . H281 . 108.834 no C29 . C28 . H281 . 108.874 no C27 . C28 . H282 . 108.157 no C29 . C28 . H282 . 108.713 no H281 . C28 . H282 . 109.528 no C28 . C29 . H291 . 111.072 no C28 . C29 . H292 . 112.021 no H291 . C29 . H292 . 106.268 no C28 . C29 . H293 . 113.782 no H291 . C29 . H293 . 106.702 no H292 . C29 . H293 . 106.537 no # Attachment '1.cif' data_yTao_c18OTPY_173k _database_code_depnum_ccdc_archive 'CCDC 274897' _audit_creation_date 04-09-29 _audit_creation_method CRYSTALS_ver_12.20 # 9271320 yTao_cisOTPY_173k #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment mixed #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 51.0346(8) _cell_angle_alpha 90 _cell_length_b 5.47280(10) _cell_angle_beta 95.9507(7) _cell_length_c 20.8564(3) _cell_angle_gamma 90 _cell_volume 5793.85(16) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . 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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B '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_IV_Table_2.2B _cell_formula_units_Z 8 _chemical_formula_sum ' C33 H47 N3 O1 ' _chemical_formula_moiety ' C33 H47 N3 O1 ' _chemical_compound_source ; ? ; _chemical_formula_weight 501.76 _cell_measurement_reflns_used 7599 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _cell_measurement_temperature 173 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colorless ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.150 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 0.069 _diffrn_measurement_device_type ; Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR97 (Altomare et al, 1999) ; _diffrn_measurement_method '\f & \w scans' _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 # Sheldrick geometric definitions 0.99 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 173 _diffrn_reflns_number 13763 _reflns_number_total 6889 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 6889 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6900 _diffrn_reflns_theta_min 2.945 _diffrn_reflns_theta_max 27.868 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.868 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -65 _diffrn_reflns_limit_h_max 66 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _reflns_limit_h_min -66 _reflns_limit_h_max 66 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _refine_diff_density_min -0.18 _refine_diff_density_max 0.18 _refine_ls_number_reflns 3362 _refine_ls_number_restraints 0 _refine_ls_number_parameters 335 #_refine_ls_R_factor_ref 0.0365 _refine_ls_wR_factor_ref 0.0459 _refine_ls_goodness_of_fit_ref 0.9880 #_reflns_number_all 3809 _refine_ls_R_factor_all 0.0410 _refine_ls_wR_factor_all 0.0473 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3362 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_gt 0.0459 _refine_ls_shift/su_max 0.001028 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.228E-01 0.300E-01 0.00 0.00 0.00 0.333 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Grazia, A., Moliterni, G., Polidori, G. and Spagna, R. (1999) SIR97: a new tool for crystal structure determination and refinement.J. App. Cryst. 32, 115-119 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. 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 trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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 0.91160(2) 0.3883(2) 0.09545(5) 0.0330 1.0000 Uani . . . . . . N1 N 0.92031(3) 0.5261(3) 0.33919(6) 0.0349 1.0000 Uani . . . . . . N2 N 0.95129(3) 0.8777(2) 0.22231(6) 0.0269 1.0000 Uani . . . . . . N3 N 0.97763(3) 1.0543(3) 0.07536(6) 0.0328 1.0000 Uani . . . . . . C1 C 0.91863(3) 0.5247(3) 0.40284(8) 0.0378 1.0000 Uani . . . . . . C2 C 0.92972(3) 0.6986(3) 0.44479(8) 0.0343 1.0000 Uani . . . . . . C3 C 0.94310(3) 0.8908(3) 0.42002(8) 0.0335 1.0000 Uani . . . . . . C4 C 0.94508(3) 0.8972(3) 0.35434(7) 0.0304 1.0000 Uani . . . . . . C5 C 0.93365(3) 0.7127(3) 0.31562(7) 0.0268 1.0000 Uani . . . . . . C6 C 0.93542(3) 0.7091(3) 0.24453(7) 0.0262 1.0000 Uani . . . . . . C7 C 0.92124(3) 0.5386(3) 0.20498(7) 0.0280 1.0000 Uani . . . . . . C8 C 0.92398(3) 0.5432(3) 0.13974(7) 0.0266 1.0000 Uani . . . . . . C9 C 0.94053(3) 0.7154(3) 0.11589(7) 0.0275 1.0000 Uani . . . . . . C10 C 0.95367(3) 0.8789(3) 0.15852(7) 0.0253 1.0000 Uani . . . . . . C11 C 0.97175(3) 1.0683(3) 0.13666(7) 0.0257 1.0000 Uani . . . . . . C12 C 0.98178(3) 1.2498(3) 0.17903(8) 0.0306 1.0000 Uani . . . . . . C13 C 0.99891(3) 1.4219(3) 0.15793(8) 0.0332 1.0000 Uani . . . . . . C14 C 1.00530(3) 1.4080(3) 0.09566(8) 0.0342 1.0000 Uani . . . . . . C15 C 0.99416(3) 1.2246(3) 0.05642(8) 0.0367 1.0000 Uani . . . . . . C16 C 0.89337(3) 0.2114(3) 0.11694(8) 0.0295 1.0000 Uani . . . . . . C17 C 0.88344(3) 0.0630(3) 0.05814(8) 0.0298 1.0000 Uani . . . . . . C18 C 0.86223(3) -0.1200(3) 0.07193(8) 0.0309 1.0000 Uani . . . . . . C19 C 0.85280(3) -0.2720(3) 0.01277(8) 0.0320 1.0000 Uani . . . . . . C20 C 0.83031(3) -0.4465(3) 0.02320(8) 0.0320 1.0000 Uani . . . . . . C21 C 0.82098(3) -0.5957(3) -0.03652(8) 0.0320 1.0000 Uani . . . . . . C22 C 0.79841(3) -0.7693(3) -0.02640(8) 0.0323 1.0000 Uani . . . . . . C23 C 0.78910(3) -0.9206(3) -0.08570(8) 0.0322 1.0000 Uani . . . . . . C24 C 0.76634(3) -1.0922(3) -0.07548(8) 0.0318 1.0000 Uani . . . . . . C25 C 0.75725(3) -1.2456(3) -0.13465(8) 0.0328 1.0000 Uani . . . . . . C26 C 0.73438(3) -1.4165(3) -0.12492(8) 0.0326 1.0000 Uani . . . . . . C27 C 0.72539(3) -1.5704(3) -0.18391(8) 0.0324 1.0000 Uani . . . . . . C28 C 0.70251(3) -1.7397(3) -0.17402(8) 0.0337 1.0000 Uani . . . . . . C29 C 0.69326(3) -1.8946(3) -0.23285(8) 0.0335 1.0000 Uani . . . . . . C30 C 0.67032(3) -2.0628(3) -0.22271(8) 0.0344 1.0000 Uani . . . . . . C31 C 0.66109(3) -2.2179(3) -0.28136(8) 0.0353 1.0000 Uani . . . . . . C32 C 0.63879(3) -2.3922(3) -0.27093(9) 0.0381 1.0000 Uani . . . . . . C33 C 0.62972(4) -2.5431(4) -0.33040(9) 0.0477 1.0000 Uani . . . . . . H11 H 0.90874(3) 0.3877(3) 0.42101(8) 0.0429 1.0000 Uiso R . . . . . H21 H 0.92820(3) 0.6873(3) 0.49212(8) 0.0413 1.0000 Uiso R . . . . . H31 H 0.95118(3) 1.0220(3) 0.44902(8) 0.0395 1.0000 Uiso R . . . . . H41 H 0.95468(3) 1.0331(3) 0.33486(7) 0.0367 1.0000 Uiso R . . . . . H71 H 0.90945(3) 0.4165(3) 0.22318(7) 0.0342 1.0000 Uiso R . . . . . H91 H 0.94283(3) 0.7212(3) 0.06888(7) 0.0312 1.0000 Uiso R . . . . . H121 H 0.97664(3) 1.2552(3) 0.22399(8) 0.0350 1.0000 Uiso R . . . . . H131 H 1.00644(3) 1.5534(3) 0.18764(8) 0.0393 1.0000 Uiso R . . . . . H141 H 1.01777(3) 1.5280(3) 0.07919(8) 0.0407 1.0000 Uiso R . . . . . H151 H 0.99863(3) 1.2172(3) 0.01090(8) 0.0424 1.0000 Uiso R . . . . . H161 H 0.90250(3) 0.1031(3) 0.15084(8) 0.0354 1.0000 Uiso R . . . . . H162 H 0.87832(3) 0.2962(3) 0.13463(8) 0.0354 1.0000 Uiso R . . . . . H171 H 0.89860(3) -0.0286(3) 0.04300(8) 0.0365 1.0000 Uiso R . . . . . H172 H 0.87597(3) 0.1768(3) 0.02343(8) 0.0365 1.0000 Uiso R . . . . . H181 H 0.86954(3) -0.2317(3) 0.10728(8) 0.0373 1.0000 Uiso R . . . . . H182 H 0.84686(3) -0.0285(3) 0.08603(8) 0.0373 1.0000 Uiso R . . . . . H191 H 0.86801(3) -0.3706(3) 0.00051(8) 0.0377 1.0000 Uiso R . . . . . H192 H 0.84668(3) -0.1584(3) -0.02327(8) 0.0377 1.0000 Uiso R . . . . . H201 H 0.83643(3) -0.5614(3) 0.05892(8) 0.0392 1.0000 Uiso R . . . . . H202 H 0.81511(3) -0.3485(3) 0.03576(8) 0.0392 1.0000 Uiso R . . . . . H211 H 0.83613(3) -0.6951(3) -0.04880(8) 0.0392 1.0000 Uiso R . . . . . H212 H 0.81504(3) -0.4807(3) -0.07236(8) 0.0392 1.0000 Uiso R . . . . . H221 H 0.80434(3) -0.8835(3) 0.00964(8) 0.0386 1.0000 Uiso R . . . . . H222 H 0.78325(3) -0.6697(3) -0.01434(8) 0.0386 1.0000 Uiso R . . . . . H231 H 0.80427(3) -1.0202(3) -0.09775(8) 0.0384 1.0000 Uiso R . . . . . H232 H 0.78318(3) -0.8063(3) -0.12173(8) 0.0384 1.0000 Uiso R . . . . . H241 H 0.77221(3) -1.2055(3) -0.03919(8) 0.0375 1.0000 Uiso R . . . . . H242 H 0.75111(3) -0.9925(3) -0.06382(8) 0.0375 1.0000 Uiso R . . . . . H251 H 0.77248(3) -1.3455(3) -0.14623(8) 0.0393 1.0000 Uiso R . . . . . H252 H 0.75143(3) -1.1322(3) -0.17096(8) 0.0393 1.0000 Uiso R . . . . . H261 H 0.74021(3) -1.5298(3) -0.08860(8) 0.0388 1.0000 Uiso R . . . . . H262 H 0.71917(3) -1.3165(3) -0.11329(8) 0.0388 1.0000 Uiso R . . . . . H271 H 0.74052(3) -1.6720(3) -0.19523(8) 0.0386 1.0000 Uiso R . . . . . H272 H 0.71975(3) -1.4572(3) -0.22039(8) 0.0386 1.0000 Uiso R . . . . . H281 H 0.70815(3) -1.8525(3) -0.13745(8) 0.0407 1.0000 Uiso R . . . . . H282 H 0.68738(3) -1.6378(3) -0.16277(8) 0.0407 1.0000 Uiso R . . . . . H291 H 0.70837(3) -1.9968(3) -0.24412(8) 0.0395 1.0000 Uiso R . . . . . H292 H 0.68761(3) -1.7821(3) -0.26947(8) 0.0395 1.0000 Uiso R . . . . . H301 H 0.67596(3) -2.1747(3) -0.18595(8) 0.0404 1.0000 Uiso R . . . . . H302 H 0.65520(3) -1.9605(3) -0.21162(8) 0.0404 1.0000 Uiso R . . . . . H311 H 0.67638(3) -2.3161(3) -0.29329(8) 0.0429 1.0000 Uiso R . . . . . H312 H 0.65491(3) -2.1060(3) -0.31771(8) 0.0429 1.0000 Uiso R . . . . . H321 H 0.64504(3) -2.5062(3) -0.23510(9) 0.0455 1.0000 Uiso R . . . . . H322 H 0.62358(3) -2.2944(3) -0.25832(9) 0.0455 1.0000 Uiso R . . . . . H331 H 0.61509(4) -2.6543(4) -0.32073(9) 0.0596 1.0000 Uiso R . . . . . H332 H 0.64477(4) -2.6424(4) -0.34324(9) 0.0596 1.0000 Uiso R . . . . . H333 H 0.62331(4) -2.4307(4) -0.36647(9) 0.0596 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 O1 0.0355(7) 0.0368(7) 0.0274(6) -0.0072(5) 0.0061(5) -0.0139(6) N1 0.0408(9) 0.0368(8) 0.0280(8) 0.0005(7) 0.0089(6) -0.0064(7) N2 0.0288(7) 0.0291(8) 0.0229(7) -0.0009(6) 0.0034(6) -0.0041(6) N3 0.0389(8) 0.0344(8) 0.0255(7) 0.0040(6) 0.0058(6) -0.0048(7) C1 0.0445(11) 0.0401(11) 0.0306(9) 0.0042(9) 0.0124(8) -0.0050(9) C2 0.0373(10) 0.0426(11) 0.0236(8) 0.0014(8) 0.0067(7) 0.0059(9) C3 0.0369(10) 0.0372(10) 0.0260(9) -0.0048(8) 0.0014(7) 0.0038(8) C4 0.0335(10) 0.0315(10) 0.0263(8) -0.0007(7) 0.0041(7) -0.0014(8) C5 0.0258(8) 0.0292(9) 0.0255(8) 0.0001(7) 0.0034(7) 0.0003(7) C6 0.0269(8) 0.0270(9) 0.0248(8) -0.0011(7) 0.0034(7) 0.0004(8) C7 0.0268(9) 0.0308(9) 0.0269(8) -0.0012(7) 0.0048(7) -0.0045(8) C8 0.0250(9) 0.0273(9) 0.0271(8) -0.0047(7) 0.0005(7) -0.0031(7) C9 0.0282(9) 0.0320(9) 0.0226(8) -0.0005(7) 0.0040(7) -0.0014(8) C10 0.0229(8) 0.0283(9) 0.0246(8) 0.0002(7) 0.0027(6) 0.0002(7) C11 0.0237(8) 0.0279(9) 0.0252(8) 0.0038(7) 0.0011(6) 0.0010(7) C12 0.0295(9) 0.0336(10) 0.0287(8) 0.0011(8) 0.0023(7) -0.0042(8) C13 0.0318(10) 0.0316(10) 0.0353(10) 0.0012(8) -0.0012(7) -0.0047(8) C14 0.0316(9) 0.0314(10) 0.0396(10) 0.0100(8) 0.0027(7) -0.0054(8) C15 0.0431(10) 0.0386(11) 0.0297(9) 0.0076(8) 0.0095(8) -0.0034(9) C16 0.0285(9) 0.0301(9) 0.0305(9) -0.0036(8) 0.0058(7) -0.0087(8) C17 0.0303(9) 0.0286(9) 0.0305(9) -0.0034(7) 0.0033(7) -0.0047(8) C18 0.0296(9) 0.0317(9) 0.0315(9) -0.0035(8) 0.0037(7) -0.0058(8) C19 0.0348(9) 0.0302(10) 0.0308(9) -0.0046(8) 0.0031(7) -0.0063(8) C20 0.0331(9) 0.0291(9) 0.0337(9) -0.0050(8) 0.0030(7) -0.0065(8) C21 0.0321(10) 0.0292(9) 0.0341(9) -0.0021(8) 0.0016(7) -0.0052(8) C22 0.0320(9) 0.0302(9) 0.0344(9) -0.0035(8) 0.0030(7) -0.0062(8) C23 0.0316(10) 0.0309(10) 0.0340(9) -0.0025(8) 0.0030(7) -0.0061(8) C24 0.0317(9) 0.0302(9) 0.0338(9) -0.0053(8) 0.0051(7) -0.0074(8) C25 0.0342(9) 0.0304(10) 0.0340(9) -0.0044(8) 0.0039(7) -0.0069(8) C26 0.0308(9) 0.0315(9) 0.0355(9) -0.0045(8) 0.0040(7) -0.0064(8) C27 0.0329(10) 0.0290(9) 0.0349(9) -0.0029(8) 0.0021(7) -0.0062(8) C28 0.0333(9) 0.0324(10) 0.0354(9) -0.0043(8) 0.0037(7) -0.0068(8) C29 0.0350(10) 0.0307(9) 0.0350(9) -0.0034(8) 0.0036(8) -0.0057(8) C30 0.0343(10) 0.0331(10) 0.0361(9) -0.0063(8) 0.0057(8) -0.0077(8) C31 0.0359(10) 0.0348(10) 0.0351(9) -0.0042(8) 0.0027(7) -0.0060(9) C32 0.0324(10) 0.0381(10) 0.0438(10) -0.0053(9) 0.0037(8) -0.0076(9) C33 0.0432(11) 0.0438(12) 0.0543(12) -0.0085(10) -0.0031(9) -0.0130(10) _refine_ls_extinction_coef 220(40) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' 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 . C8 . 1.3601(18) yes O1 . C16 . 1.4458(18) yes N1 . C1 . 1.339(2) yes N1 . C5 . 1.348(2) yes N2 . C6 . 1.3415(19) yes N2 . C10 . 1.3484(19) yes N3 . C11 . 1.3452(19) yes N3 . C15 . 1.344(2) yes C1 . C2 . 1.375(2) yes C1 . H11 . 1.000 no C2 . C3 . 1.383(2) yes C2 . H21 . 1.000 no C3 . C4 . 1.385(2) yes C3 . H31 . 1.000 no C4 . C5 . 1.383(2) yes C4 . H41 . 1.000 no C5 . C6 . 1.495(2) yes C6 . C7 . 1.397(2) yes C7 . C8 . 1.382(2) yes C7 . H71 . 1.000 no C8 . C9 . 1.392(2) yes C9 . C10 . 1.384(2) yes C9 . H91 . 1.000 no C10 . C11 . 1.491(2) yes C11 . C12 . 1.391(2) yes C12 . C13 . 1.387(2) yes C12 . H121 . 1.000 no C13 . C14 . 1.373(2) yes C13 . H131 . 1.000 no C14 . C15 . 1.380(2) yes C14 . H141 . 1.000 no C15 . H151 . 1.000 no C16 . C17 . 1.514(2) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . C18 . 1.524(2) yes C17 . H171 . 1.000 no C17 . H172 . 1.000 no C18 . C19 . 1.524(2) yes C18 . H181 . 1.000 no C18 . H182 . 1.000 no C19 . C20 . 1.526(2) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C20 . C21 . 1.524(2) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C21 . C22 . 1.524(2) yes C21 . H211 . 1.000 no C21 . H212 . 1.000 no C22 . C23 . 1.523(2) yes C22 . H221 . 1.000 no C22 . H222 . 1.000 no C23 . C24 . 1.526(2) yes C23 . H231 . 1.000 no C23 . H232 . 1.000 no C24 . C25 . 1.525(2) yes C24 . H241 . 1.000 no C24 . H242 . 1.000 no C25 . C26 . 1.525(2) yes C25 . H251 . 1.000 no C25 . H252 . 1.000 no C26 . C27 . 1.522(2) yes C26 . H261 . 1.000 no C26 . H262 . 1.000 no C27 . C28 . 1.521(2) yes C27 . H271 . 1.000 no C27 . H272 . 1.000 no C28 . C29 . 1.525(2) yes C28 . H281 . 1.000 no C28 . H282 . 1.000 no C29 . C30 . 1.521(2) yes C29 . H291 . 1.000 no C29 . H292 . 1.000 no C30 . C31 . 1.523(2) yes C30 . H301 . 1.000 no C30 . H302 . 1.000 no C31 . C32 . 1.517(2) yes C31 . H311 . 1.000 no C31 . H312 . 1.000 no C32 . C33 . 1.522(2) yes C32 . H321 . 1.000 no C32 . H322 . 1.000 no C33 . H331 . 1.000 no C33 . H332 . 1.000 no C33 . H333 . 1.000 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 C8 . O1 . C16 . 118.37(12) yes C1 . N1 . C5 . 116.91(15) yes C6 . N2 . C10 . 117.62(13) yes C11 . N3 . C15 . 116.64(14) yes N1 . C1 . C2 . 124.23(17) yes N1 . C1 . H11 . 117.825 no C2 . C1 . H11 . 117.947 no C1 . C2 . C3 . 118.40(16) yes C1 . C2 . H21 . 121.103 no C3 . C2 . H21 . 120.500 no C2 . C3 . C4 . 118.59(16) yes C2 . C3 . H31 . 120.587 no C4 . C3 . H31 . 120.823 no C3 . C4 . C5 . 119.30(16) yes C3 . C4 . H41 . 120.658 no C5 . C4 . H41 . 120.040 no C4 . C5 . N1 . 122.57(15) yes C4 . C5 . C6 . 121.57(15) yes N1 . C5 . C6 . 115.86(14) yes C5 . C6 . N2 . 115.73(14) yes C5 . C6 . C7 . 120.92(14) yes N2 . C6 . C7 . 123.34(14) yes C6 . C7 . C8 . 118.05(14) yes C6 . C7 . H71 . 121.154 no C8 . C7 . H71 . 120.799 no C7 . C8 . O1 . 124.75(14) yes C7 . C8 . C9 . 119.41(14) yes O1 . C8 . C9 . 115.84(13) yes C8 . C9 . C10 . 118.66(14) yes C8 . C9 . H91 . 120.600 no C10 . C9 . H91 . 120.736 no C9 . C10 . N2 . 122.91(14) yes C9 . C10 . C11 . 121.80(14) yes N2 . C10 . C11 . 115.29(14) yes C10 . C11 . N3 . 117.20(14) yes C10 . C11 . C12 . 120.06(14) yes N3 . C11 . C12 . 122.74(15) yes C11 . C12 . C13 . 119.05(15) yes C11 . C12 . H121 . 120.123 no C13 . C12 . H121 . 120.827 no C12 . C13 . C14 . 118.78(16) yes C12 . C13 . H131 . 120.414 no C14 . C13 . H131 . 120.805 no C13 . C14 . C15 . 118.53(16) yes C13 . C14 . H141 . 120.689 no C15 . C14 . H141 . 120.784 no C14 . C15 . N3 . 124.25(16) yes C14 . C15 . H151 . 118.175 no N3 . C15 . H151 . 117.575 no O1 . C16 . C17 . 106.27(12) yes O1 . C16 . H161 . 110.391 no C17 . C16 . H161 . 110.318 no O1 . C16 . H162 . 110.324 no C17 . C16 . H162 . 110.033 no H161 . C16 . H162 . 109.467 no C16 . C17 . C18 . 112.60(13) yes C16 . C17 . H171 . 108.654 no C18 . C17 . H171 . 108.555 no C16 . C17 . H172 . 108.835 no C18 . C17 . H172 . 108.699 no H171 . C17 . H172 . 109.466 no C17 . C18 . C19 . 112.13(13) yes C17 . C18 . H181 . 108.842 no C19 . C18 . H181 . 108.985 no C17 . C18 . H182 . 108.737 no C19 . C18 . H182 . 108.654 no H181 . C18 . H182 . 109.467 no C18 . C19 . C20 . 113.89(13) yes C18 . C19 . H191 . 108.250 no C20 . C19 . H191 . 108.327 no C18 . C19 . H192 . 108.479 no C20 . C19 . H192 . 108.369 no H191 . C19 . H192 . 109.467 no C19 . C20 . C21 . 113.24(13) yes C19 . C20 . H201 . 108.553 no C21 . C20 . H201 . 108.580 no C19 . C20 . H202 . 108.497 no C21 . C20 . H202 . 108.455 no H201 . C20 . H202 . 109.467 no C20 . C21 . C22 . 113.41(13) yes C20 . C21 . H211 . 108.449 no C22 . C21 . H211 . 108.187 no C20 . C21 . H212 . 108.555 no C22 . C21 . H212 . 108.725 no H211 . C21 . H212 . 109.467 no C21 . C22 . C23 . 113.77(13) yes C21 . C22 . H221 . 108.631 no C23 . C22 . H221 . 108.380 no C21 . C22 . H222 . 108.103 no C23 . C22 . H222 . 108.435 no H221 . C22 . H222 . 109.467 no C22 . C23 . C24 . 113.54(13) yes C22 . C23 . H231 . 108.412 no C24 . C23 . H231 . 108.668 no C22 . C23 . H232 . 108.357 no C24 . C23 . H232 . 108.350 no H231 . C23 . H232 . 109.466 no C23 . C24 . C25 . 113.47(13) yes C23 . C24 . H241 . 108.361 no C25 . C24 . H241 . 108.254 no C23 . C24 . H242 . 108.690 no C25 . C24 . H242 . 108.547 no H241 . C24 . H242 . 109.467 no C24 . C25 . C26 . 113.76(13) yes C24 . C25 . H251 . 108.508 no C26 . C25 . H251 . 108.763 no C24 . C25 . H252 . 108.212 no C26 . C25 . H252 . 108.075 no H251 . C25 . H252 . 109.467 no C25 . C26 . C27 . 113.73(13) yes C25 . C26 . H261 . 108.012 no C27 . C26 . H261 . 108.073 no C25 . C26 . H262 . 108.698 no C27 . C26 . H262 . 108.801 no H261 . C26 . H262 . 109.467 no C26 . C27 . C28 . 113.51(14) yes C26 . C27 . H271 . 108.863 no C28 . C27 . H271 . 108.389 no C26 . C27 . H272 . 108.120 no C28 . C27 . H272 . 108.439 no H271 . C27 . H272 . 109.467 no C27 . C28 . C29 . 114.05(14) yes C27 . C28 . H281 . 108.368 no C29 . C28 . H281 . 108.125 no C27 . C28 . H282 . 108.321 no C29 . C28 . H282 . 108.452 no H281 . C28 . H282 . 109.467 no C28 . C29 . C30 . 113.77(13) yes C28 . C29 . H291 . 108.550 no C30 . C29 . H291 . 108.505 no C28 . C29 . H292 . 108.222 no C30 . C29 . H292 . 108.269 no H291 . C29 . H292 . 109.467 no C29 . C30 . C31 . 113.84(14) yes C29 . C30 . H301 . 108.222 no C31 . C30 . H301 . 108.358 no C29 . C30 . H302 . 108.466 no C31 . C30 . H302 . 108.428 no H301 . C30 . H302 . 109.467 no C30 . C31 . C32 . 114.17(14) yes C30 . C31 . H311 . 108.345 no C32 . C31 . H311 . 108.322 no C30 . C31 . H312 . 108.325 no C32 . C31 . H312 . 108.152 no H311 . C31 . H312 . 109.467 no C31 . C32 . C33 . 113.17(15) yes C31 . C32 . H321 . 108.242 no C33 . C32 . H321 . 108.508 no C31 . C32 . H322 . 108.382 no C33 . C32 . H322 . 109.021 no H321 . C32 . H322 . 109.467 no C32 . C33 . H331 . 109.654 no C32 . C33 . H332 . 109.631 no H331 . C33 . H332 . 109.474 no C32 . C33 . H333 . 109.115 no H331 . C33 . H333 . 109.476 no H332 . C33 . H333 . 109.477 no