data_ban1122 # 1. SUBMISSION DETAILS _publ_requested_journal J.Org.Chem. _publ_contact_author_name 'Martin G. Banwell' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia ; _publ_contact_author_email ' mgb@rsc.anu.edu.au ' _publ_contact_author_phone ' 61 2 6125 8202 ' _publ_contact_author_fax ' 61 2 6125 8114 ' loop_ _publ_author_name _publ_author_address 'Schwartz, Brett D.' ; Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia ; 'White, Lorenzo V.' ; Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia ; 'Banwell, Martin G.' ; Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia ; 'Willis, Anthony C.' ; Research School of Chemistry, The Australian National University, Canberra, ACT 0200, Australia ; _audit_creation_date 11-07-25 _audit_creation_method CRYSTALS_ver_14.11 _audit_update_record ; 2011-07-25 - Report on C24 H23 N O6 by Anthony C. Willis for Brett Schwartz and Martin Banwell 2011-07-25 - passes checkcif tests with no warnings ; _oxford_structure_analysis_title '7250903 ban1122 scalepacked, relabelled' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.4886(2) _cell_length_b 12.6225(3) _cell_length_c 19.7837(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2119.77(8) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C24 H23 N1 O6 # Dc = 1.32 Fooo = 888.00 Mu = 0.95 M = 421.45 # Found Formula = C24 H23 N1 O6 # Dc = 1.32 FOOO = 888.00 Mu = 0.95 M = 421.45 _chemical_formula_sum 'C24 H23 N1 O6' _chemical_formula_moiety 'C24 H23 N1 O6' _chemical_compound_source local _chemical_formula_weight 421.45 _cell_measurement_reflns_used 23443 _cell_measurement_theta_min 3 _cell_measurement_theta_max 30 _cell_measurement_temperature 200 _exptl_crystal_description block _exptl_crystal_colour 'pale brown' _exptl_crystal_size_min 0.180 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_max 0.400 _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.095 # Sheldrick geometric approximatio 0.96 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.89 # scalepacked 0.98*9.81/10.74=.89 ; 0.96 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 1.5 deg at rate 165 sec/frame and at 16.5 sec/frame, crystal-detector distance 40mm, multiple scan sets so over 90 percent of data collected with 4-fold redundancy or more (assuming Friedel's Law]. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 45483 _reflns_number_total 3482 _diffrn_reflns_av_R_equivalents 0.048 # scalepack # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3482 # Theoretical number of reflections is about 6199 _diffrn_reflns_theta_min 2.611 _diffrn_reflns_theta_max 30.028 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.028 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _reflns_limit_h_min 0 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _oxford_diffrn_Wilson_B_factor 3.25 _oxford_diffrn_Wilson_scale 1.08 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.18 _refine_diff_density_max 0.18 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 3482 _refine_ls_number_restraints 0 _refine_ls_number_parameters 349 _oxford_refine_ls_R_factor_ref 0.0412 _refine_ls_wR_factor_ref 0.0911 _refine_ls_goodness_of_fit_ref 0.9907 _refine_ls_shift/su_max 0.0100884 _refine_ls_shift/su_mean 0.0015292 # The values computed from all data _oxford_reflns_number_all 3482 _refine_ls_R_factor_all 0.0412 _refine_ls_wR_factor_all 0.0911 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3077 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_gt 0.0868 # 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 syn _refine_ls_abs_structure_details ; The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refxyz # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.25P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_requested_category FO _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; The Structure of the Lycorenine Alkaloid Nobilisitine A ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~24~H~23~NO~6~ is reported. ; _publ_section_comment #Text of the paper ; The crystallographic asymmetric unit consists of one C~24~H~23~NO~6~ molecule. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement ; ; _refine_special_details ; Anomolous dispersion terms are very low for all elements in the structure and so the absolute configuration can not be determined in this experiment. Consequently Friedel-pair reflections have been averaged and the Flack parameter has not been refined. The absolute configuration of the molecule has been assigned on the basis of the synthetic precursors. The H atoms were all located in a difference map, but were repositioned geometrically. They were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98\%A) and with U~iso~(H) in the range 1.2-1.5 times U~eq~ of the parent atom, after which the positions were refined without restraints and the displacement parameters were held fixed. The largest peaks in the final difference electron density map are located near O25, external to the molecule or midway along C---C bonds. ; _publ_section_exptl_prep ; The compound was prepared by BDS and recrystallised from deuterated chloroform / ethylacetate. The sample ID is BS-3-153. ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 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. Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # 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 0.31350(15) 0.51519(12) 0.38095(6) 0.0429 1.0000 Uani . . . . . . C2 C 0.7602(2) 0.39743(14) 0.43146(9) 0.0415 1.0000 Uani . . . . . . C3 C 0.68426(18) 0.48918(13) 0.39477(7) 0.0379 1.0000 Uani . . . . . . C4 C 0.55334(17) 0.54065(12) 0.43623(7) 0.0344 1.0000 Uani . . . . . . C5 C 0.4908(2) 0.64601(14) 0.40601(9) 0.0422 1.0000 Uani . . . . . . C6 C 0.31312(19) 0.62631(15) 0.40372(8) 0.0438 1.0000 Uani . . . . . . C7 C 0.2474(2) 0.62079(15) 0.47695(8) 0.0455 1.0000 Uani . . . . . . C8 C 0.30222(17) 0.51109(13) 0.50115(7) 0.0385 1.0000 Uani . . . . . . C9 C 0.40199(17) 0.47378(13) 0.43935(7) 0.0358 1.0000 Uani . . . . . . C10 C 0.1590(2) 0.4670(2) 0.36866(10) 0.0620 1.0000 Uani . . . . . . C11 C 0.38623(17) 0.50768(13) 0.56762(7) 0.0374 1.0000 Uani . . . . . . C12 C 0.4317(2) 0.40903(14) 0.59398(8) 0.0435 1.0000 Uani . . . . . . C13 C 0.5140(2) 0.41008(15) 0.65385(8) 0.0458 1.0000 Uani . . . . . . O14 O 0.5675(2) 0.32525(12) 0.69006(7) 0.0652 1.0000 Uani . . . . . . C15 C 0.6573(3) 0.3697(2) 0.74470(10) 0.0613 1.0000 Uani . . . . . . O16 O 0.63063(17) 0.48069(12) 0.74585(6) 0.0586 1.0000 Uani . . . . . . C17 C 0.55113(19) 0.50376(15) 0.68707(7) 0.0435 1.0000 Uani . . . . . . C18 C 0.5090(2) 0.59986(15) 0.66256(8) 0.0431 1.0000 Uani . . . . . . C19 C 0.42463(18) 0.60127(13) 0.60093(7) 0.0383 1.0000 Uani . . . . . . C20 C 0.3830(2) 0.70566(14) 0.57309(8) 0.0434 1.0000 Uani . . . . . . O21 O 0.30038(17) 0.71204(10) 0.51546(6) 0.0532 1.0000 Uani . . . . . . O22 O 0.42152(19) 0.78849(10) 0.59958(7) 0.0560 1.0000 Uani . . . . . . O23 O 0.83218(14) 0.44171(9) 0.49216(6) 0.0434 1.0000 Uani . . . . . . C24 C 0.8953(2) 0.37464(14) 0.53590(9) 0.0490 1.0000 Uani . . . . . . O25 O 0.9035(3) 0.28126(12) 0.52567(9) 0.0961 1.0000 Uani . . . . . . C26 C 0.9539(2) 0.42782(15) 0.59788(8) 0.0471 1.0000 Uani . . . . . . C27 C 1.0345(3) 0.3675(2) 0.64579(11) 0.0669 1.0000 Uani . . . . . . C28 C 1.0907(3) 0.4151(3) 0.70441(11) 0.0780 1.0000 Uani . . . . . . C29 C 1.0674(3) 0.5204(3) 0.71539(11) 0.0728 1.0000 Uani . . . . . . C30 C 0.9904(3) 0.5801(2) 0.66804(11) 0.0707 1.0000 Uani . . . . . . C31 C 0.9326(2) 0.53499(17) 0.60914(9) 0.0523 1.0000 Uani . . . . . . H21 H 0.847(3) 0.3657(15) 0.4044(10) 0.0504 1.0000 Uiso . . . . . . H22 H 0.684(2) 0.3406(16) 0.4464(10) 0.0491 1.0000 Uiso . . . . . . H31 H 0.646(2) 0.4656(15) 0.3503(10) 0.0454 1.0000 Uiso . . . . . . H32 H 0.766(2) 0.5438(15) 0.3838(10) 0.0460 1.0000 Uiso . . . . . . H41 H 0.595(2) 0.5531(14) 0.4829(9) 0.0388 1.0000 Uiso . . . . . . H51 H 0.528(3) 0.6575(17) 0.3601(11) 0.0508 1.0000 Uiso . . . . . . H52 H 0.527(2) 0.7093(16) 0.4351(10) 0.0498 1.0000 Uiso . . . . . . H61 H 0.250(2) 0.6746(17) 0.3737(10) 0.0523 1.0000 Uiso . . . . . . H71 H 0.133(3) 0.6288(16) 0.4756(10) 0.0552 1.0000 Uiso . . . . . . H81 H 0.203(2) 0.4646(15) 0.5023(10) 0.0462 1.0000 Uiso . . . . . . H91 H 0.418(2) 0.3950(16) 0.4368(10) 0.0418 1.0000 Uiso . . . . . . H101 H 0.173(4) 0.394(2) 0.3606(15) 0.0913 1.0000 Uiso . . . . . . H102 H 0.110(4) 0.498(2) 0.3261(15) 0.0921 1.0000 Uiso . . . . . . H103 H 0.086(4) 0.479(2) 0.4074(15) 0.0914 1.0000 Uiso . . . . . . H121 H 0.408(2) 0.3416(16) 0.5700(11) 0.0526 1.0000 Uiso . . . . . . H151 H 0.617(3) 0.3394(19) 0.7855(12) 0.0732 1.0000 Uiso . . . . . . H152 H 0.769(3) 0.350(2) 0.7320(13) 0.0750 1.0000 Uiso . . . . . . H181 H 0.536(3) 0.6647(17) 0.6847(11) 0.0514 1.0000 Uiso . . . . . . H271 H 1.043(3) 0.293(2) 0.6366(13) 0.0811 1.0000 Uiso . . . . . . H281 H 1.147(4) 0.369(2) 0.7354(16) 0.0935 1.0000 Uiso . . . . . . H291 H 1.103(4) 0.557(2) 0.7579(14) 0.0868 1.0000 Uiso . . . . . . H301 H 0.967(4) 0.659(2) 0.6780(14) 0.0860 1.0000 Uiso . . . . . . H311 H 0.881(3) 0.5756(17) 0.5773(12) 0.0631 1.0000 Uiso . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0342(6) 0.0641(9) 0.0305(6) -0.0018(6) -0.0032(5) -0.0043(6) C2 0.0386(7) 0.0433(8) 0.0428(8) -0.0068(7) 0.0016(6) 0.0004(7) C3 0.0350(6) 0.0486(8) 0.0302(6) -0.0022(6) 0.0033(5) -0.0026(6) C4 0.0315(6) 0.0416(7) 0.0300(6) 0.0003(6) 0.0004(5) -0.0021(6) C5 0.0421(8) 0.0447(8) 0.0398(8) 0.0047(7) 0.0004(7) 0.0006(7) C6 0.0387(7) 0.0584(10) 0.0343(7) 0.0046(7) -0.0038(6) 0.0072(7) C7 0.0370(7) 0.0636(10) 0.0360(7) -0.0030(7) -0.0011(6) 0.0091(8) C8 0.0318(6) 0.0529(9) 0.0307(6) -0.0021(6) 0.0019(5) -0.0038(7) C9 0.0327(6) 0.0464(8) 0.0284(6) -0.0019(6) 0.0018(5) -0.0056(6) C10 0.0398(8) 0.1027(18) 0.0436(9) -0.0088(11) -0.0067(7) -0.0138(11) C11 0.0352(7) 0.0480(8) 0.0288(6) -0.0017(6) 0.0046(5) -0.0024(7) C12 0.0520(9) 0.0459(8) 0.0327(7) 0.0001(6) 0.0030(7) -0.0074(7) C13 0.0505(9) 0.0523(9) 0.0346(7) 0.0064(7) 0.0039(7) -0.0006(8) O14 0.0915(11) 0.0591(8) 0.0451(7) 0.0131(6) -0.0115(7) 0.0020(8) C15 0.0636(12) 0.0818(15) 0.0386(9) 0.0144(9) -0.0026(9) 0.0062(11) O16 0.0636(8) 0.0776(9) 0.0344(6) 0.0054(6) -0.0102(5) 0.0000(8) C17 0.0409(7) 0.0627(10) 0.0269(6) 0.0013(7) 0.0013(6) -0.0034(8) C18 0.0440(8) 0.0524(9) 0.0329(7) -0.0061(7) 0.0019(6) -0.0034(8) C19 0.0363(7) 0.0479(8) 0.0308(6) -0.0025(6) 0.0047(6) 0.0002(6) C20 0.0445(8) 0.0502(8) 0.0355(7) -0.0049(7) 0.0070(6) 0.0071(7) O21 0.0650(8) 0.0526(7) 0.0421(6) -0.0035(5) -0.0031(6) 0.0172(6) O22 0.0707(8) 0.0465(6) 0.0508(7) -0.0092(6) 0.0072(7) 0.0038(6) O23 0.0446(6) 0.0446(6) 0.0410(6) 0.0006(5) -0.0071(5) 0.0027(5) C24 0.0569(10) 0.0486(9) 0.0417(8) 0.0051(7) 0.0054(8) 0.0141(8) O25 0.171(2) 0.0499(7) 0.0674(9) -0.0022(7) -0.0252(12) 0.0332(12) C26 0.0419(8) 0.0631(10) 0.0364(7) 0.0073(7) 0.0047(7) 0.0067(8) C27 0.0649(12) 0.0892(16) 0.0467(10) 0.0165(11) 0.0032(9) 0.0232(12) C28 0.0564(12) 0.135(3) 0.0424(10) 0.0253(13) -0.0029(9) 0.0132(15) C29 0.0636(13) 0.115(2) 0.0400(9) 0.0056(12) -0.0028(9) -0.0182(15) C30 0.0810(16) 0.0830(15) 0.0482(11) -0.0022(11) -0.0076(11) -0.0191(14) C31 0.0542(10) 0.0618(10) 0.0408(8) 0.0042(8) -0.0029(8) -0.0042(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.068(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C6 . 1.473(2) yes N1 . C9 . 1.474(2) yes N1 . C10 . 1.466(2) yes C2 . C3 . 1.511(2) yes C2 . O23 . 1.459(2) yes C2 . H21 . 1.00(2) no C2 . H22 . 1.01(2) no C3 . C4 . 1.526(2) yes C3 . H31 . 0.98(2) no C3 . H32 . 1.00(2) no C4 . C5 . 1.552(2) yes C4 . C9 . 1.538(2) yes C4 . H41 . 1.003(18) no C5 . C6 . 1.530(2) yes C5 . H51 . 0.97(2) no C5 . H52 . 1.03(2) no C6 . C7 . 1.554(2) yes C6 . H61 . 1.00(2) no C7 . C8 . 1.537(2) yes C7 . O21 . 1.452(2) yes C7 . H71 . 0.97(2) no C8 . C9 . 1.560(2) yes C8 . C11 . 1.496(2) yes C8 . H81 . 1.03(2) no C9 . H91 . 1.004(19) no C10 . H101 . 0.94(3) no C10 . H102 . 1.02(3) no C10 . H103 . 1.00(3) no C11 . C12 . 1.404(2) yes C11 . C19 . 1.392(2) yes C12 . C13 . 1.375(2) yes C12 . H121 . 0.99(2) no C13 . O14 . 1.366(2) yes C13 . C17 . 1.389(3) yes O14 . C15 . 1.437(3) yes C15 . O16 . 1.419(3) yes C15 . H151 . 0.96(2) no C15 . H152 . 1.01(3) no O16 . C17 . 1.3757(19) yes C17 . C18 . 1.354(3) yes C18 . C19 . 1.414(2) yes C18 . H181 . 0.96(2) no C19 . C20 . 1.471(2) yes C20 . O21 . 1.341(2) yes C20 . O22 . 1.214(2) yes O23 . C24 . 1.324(2) yes C24 . O25 . 1.198(2) yes C24 . C26 . 1.484(3) yes C26 . C27 . 1.395(3) yes C26 . C31 . 1.383(3) yes C27 . C28 . 1.391(4) yes C27 . H271 . 0.96(3) no C28 . C29 . 1.361(4) yes C28 . H281 . 0.97(3) no C29 . C30 . 1.368(4) yes C29 . H291 . 1.01(3) no C30 . C31 . 1.387(3) yes C30 . H301 . 1.04(3) no C31 . H311 . 0.92(2) 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 C6 . N1 . C9 . 95.68(11) yes C6 . N1 . C10 . 116.35(16) yes C9 . N1 . C10 . 116.02(15) yes C3 . C2 . O23 . 106.29(13) yes C3 . C2 . H21 . 111.5(11) no O23 . C2 . H21 . 106.6(12) no C3 . C2 . H22 . 114.2(11) no O23 . C2 . H22 . 107.4(11) no H21 . C2 . H22 . 110.4(15) no C2 . C3 . C4 . 112.26(12) yes C2 . C3 . H31 . 109.7(11) no C4 . C3 . H31 . 111.7(12) no C2 . C3 . H32 . 109.5(11) no C4 . C3 . H32 . 109.2(11) no H31 . C3 . H32 . 104.1(15) no C3 . C4 . C5 . 114.00(12) yes C3 . C4 . C9 . 113.33(12) yes C5 . C4 . C9 . 101.55(12) yes C3 . C4 . H41 . 107.7(11) no C5 . C4 . H41 . 110.0(10) no C9 . C4 . H41 . 110.2(10) no C4 . C5 . C6 . 102.08(14) yes C4 . C5 . H51 . 112.2(13) no C6 . C5 . H51 . 108.3(13) no C4 . C5 . H52 . 110.3(11) no C6 . C5 . H52 . 115.9(11) no H51 . C5 . H52 . 108.0(17) no C5 . C6 . N1 . 99.30(13) yes C5 . C6 . C7 . 109.49(14) yes N1 . C6 . C7 . 104.08(14) yes C5 . C6 . H61 . 116.2(12) no N1 . C6 . H61 . 113.5(12) no C7 . C6 . H61 . 112.9(12) no C6 . C7 . C8 . 102.84(13) yes C6 . C7 . O21 . 110.03(15) yes C8 . C7 . O21 . 117.22(13) yes C6 . C7 . H71 . 109.1(12) no C8 . C7 . H71 . 113.7(12) no O21 . C7 . H71 . 103.9(12) no C7 . C8 . C9 . 101.07(12) yes C7 . C8 . C11 . 116.35(13) yes C9 . C8 . C11 . 114.91(12) yes C7 . C8 . H81 . 105.8(11) no C9 . C8 . H81 . 106.9(11) no C11 . C8 . H81 . 110.8(11) no C4 . C9 . C8 . 108.62(12) yes C4 . C9 . N1 . 101.51(11) yes C8 . C9 . N1 . 103.33(12) yes C4 . C9 . H91 . 115.4(11) no C8 . C9 . H91 . 114.3(11) no N1 . C9 . H91 . 112.3(11) no N1 . C10 . H101 . 108.8(20) no N1 . C10 . H102 . 110.1(17) no H101 . C10 . H102 . 107(2) no N1 . C10 . H103 . 111.4(16) no H101 . C10 . H103 . 111(2) no H102 . C10 . H103 . 109(2) no C8 . C11 . C12 . 118.88(14) yes C8 . C11 . C19 . 120.22(14) yes C12 . C11 . C19 . 120.84(14) yes C11 . C12 . C13 . 116.81(15) yes C11 . C12 . H121 . 121.7(12) no C13 . C12 . H121 . 121.4(12) no C12 . C13 . O14 . 127.81(17) yes C12 . C13 . C17 . 122.07(16) yes O14 . C13 . C17 . 110.10(15) yes C13 . O14 . C15 . 105.35(15) yes O14 . C15 . O16 . 108.25(16) yes O14 . C15 . H151 . 106.8(15) no O16 . C15 . H151 . 108.9(14) no O14 . C15 . H152 . 102.4(15) no O16 . C15 . H152 . 113.2(15) no H151 . C15 . H152 . 117(2) no C15 . O16 . C17 . 105.87(15) yes C13 . C17 . O16 . 109.34(16) yes C13 . C17 . C18 . 122.22(14) yes O16 . C17 . C18 . 128.44(16) yes C17 . C18 . C19 . 116.97(15) yes C17 . C18 . H181 . 122.7(13) no C19 . C18 . H181 . 120.3(13) no C18 . C19 . C11 . 121.09(15) yes C18 . C19 . C20 . 117.11(15) yes C11 . C19 . C20 . 121.79(14) yes C19 . C20 . O21 . 119.85(14) yes C19 . C20 . O22 . 123.01(15) yes O21 . C20 . O22 . 117.14(16) yes C7 . O21 . C20 . 124.07(13) yes C2 . O23 . C24 . 117.56(13) yes O23 . C24 . O25 . 122.83(19) yes O23 . C24 . C26 . 112.74(14) yes O25 . C24 . C26 . 124.43(18) yes C24 . C26 . C27 . 118.62(19) yes C24 . C26 . C31 . 122.12(16) yes C27 . C26 . C31 . 119.3(2) yes C26 . C27 . C28 . 119.9(3) yes C26 . C27 . H271 . 116.2(17) no C28 . C27 . H271 . 123.8(16) no C27 . C28 . C29 . 120.3(2) yes C27 . C28 . H281 . 115.7(18) no C29 . C28 . H281 . 124.0(17) no C28 . C29 . C30 . 119.9(2) yes C28 . C29 . H291 . 122.3(16) no C30 . C29 . H291 . 117.8(16) no C29 . C30 . C31 . 121.2(3) yes C29 . C30 . H301 . 119.5(16) no C31 . C30 . H301 . 119.2(16) no C30 . C31 . C26 . 119.4(2) yes C30 . C31 . H311 . 120.9(14) no C26 . C31 . H311 . 119.7(14) no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O16 C3 3.361(2) . 4_665 no O16 C10 3.519(2) . 4_565 no O21 C5 3.540(2) . 2_466 no O22 C15 3.315(2) . 3_656 no O22 C7 3.355(2) . 2_566 no O22 C3 3.456(2) . 2_466 no O22 C6 3.494(2) . 2_566 no O25 C9 3.293(2) . 2_556 no O25 C12 3.381(2) . 2_556 no N1 C29 3.457(2) . 4_664 no C12 C27 3.563(3) . 1_455 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O14 C13 C12 C11 . . . . 178.4(2) no O14 C13 C17 O16 . . . . 0.2(2) no O14 C13 C17 C18 . . . . -178.8(2) no O14 C15 O16 C17 . . . . -10.2(2) no O16 C15 O14 C13 . . . . 10.3(2) no O16 C17 C13 C12 . . . . 178.9(2) no O16 C17 C18 C19 . . . . -178.9(2) no O21 C7 C6 N1 . . . . 155.8(1) no O21 C7 C6 C5 . . . . 50.4(2) no O21 C7 C8 C9 . . . . -116.9(1) no O21 C7 C8 C11 . . . . 8.3(2) no O21 C20 C19 C11 . . . . 2.7(2) no O21 C20 C19 C18 . . . . -178.7(1) no O22 C20 O21 C7 . . . . 179.0(2) no O22 C20 C19 C11 . . . . -176.5(2) no O22 C20 C19 C18 . . . . 2.1(2) no O23 C2 C3 C4 . . . . -62.8(2) no O23 C24 C26 C27 . . . . -175.0(2) no O23 C24 C26 C31 . . . . 4.3(2) no O25 C24 O23 C2 . . . . 4.5(3) no O25 C24 C26 C27 . . . . 4.9(3) no O25 C24 C26 C31 . . . . -175.8(2) no N1 C6 C5 C4 . . . . -40.6(1) no N1 C6 C7 C8 . . . . 30.2(2) no N1 C9 C4 C3 . . . . -91.4(1) no N1 C9 C4 C5 . . . . 31.3(1) no N1 C9 C8 C7 . . . . -37.0(1) no N1 C9 C8 C11 . . . . -163.2(1) no C2 O23 C24 C26 . . . . -175.6(1) no C2 C3 C4 C5 . . . . 170.4(1) no C2 C3 C4 C9 . . . . -74.1(2) no C3 C2 O23 C24 . . . . 174.4(1) no C3 C4 C5 C6 . . . . 127.8(1) no C3 C4 C9 C8 . . . . 160.1(1) no C4 C5 C6 C7 . . . . 68.0(2) no C4 C9 N1 C6 . . . . -57.2(1) no C4 C9 N1 C10 . . . . 179.8(1) no C4 C9 C8 C7 . . . . 70.2(1) no C4 C9 C8 C11 . . . . -55.9(2) no C5 C4 C9 C8 . . . . -77.2(1) no C5 C6 N1 C9 . . . . 60.5(1) no C5 C6 N1 C10 . . . . -176.8(1) no C5 C6 C7 C8 . . . . -75.2(2) no C6 N1 C9 C8 . . . . 55.3(1) no C6 C5 C4 C9 . . . . 5.6(1) no C6 C7 O21 C20 . . . . -122.3(2) no C6 C7 C8 C9 . . . . 3.9(1) no C6 C7 C8 C11 . . . . 129.1(1) no C7 O21 C20 C19 . . . . -0.2(2) no C7 C6 N1 C9 . . . . -52.5(1) no C7 C6 N1 C10 . . . . 70.3(2) no C7 C8 C11 C12 . . . . 176.7(1) no C7 C8 C11 C19 . . . . -6.2(2) no C8 C7 O21 C20 . . . . -5.4(2) no C8 C9 N1 C10 . . . . -67.7(2) no C8 C11 C12 C13 . . . . 177.5(1) no C8 C11 C19 C18 . . . . -177.7(1) no C8 C11 C19 C20 . . . . 0.8(2) no C9 C8 C11 C12 . . . . -65.5(2) no C9 C8 C11 C19 . . . . 111.6(2) no C11 C12 C13 C17 . . . . -0.0(2) no C11 C19 C18 C17 . . . . 0.4(2) no C12 C11 C19 C18 . . . . -0.7(2) no C12 C11 C19 C20 . . . . 177.9(1) no C12 C13 O14 C15 . . . . 175.0(2) no C12 C13 C17 C18 . . . . -0.2(3) no C13 C12 C11 C19 . . . . 0.4(2) no C13 C17 O16 C15 . . . . 6.2(2) no C13 C17 C18 C19 . . . . -0.0(2) no C15 O14 C13 C17 . . . . -6.5(2) no C15 O16 C17 C18 . . . . -174.8(2) no C17 C18 C19 C20 . . . . -178.1(1) no C24 C26 C27 C28 . . . . -179.9(2) no C24 C26 C31 C30 . . . . -179.9(2) no C26 C27 C28 C29 . . . . 0.1(4) no C26 C31 C30 C29 . . . . -0.3(3) no C27 C26 C31 C30 . . . . -0.6(3) no C27 C28 C29 C30 . . . . -1.0(4) no C28 C27 C26 C31 . . . . 0.8(3) no C28 C29 C30 C31 . . . . 1.2(4) no #------------------------------------------------------------------------------ _iucr_refine_instruction_details_constraints ; # # Punched on 25/07/11 at 14:18:25 # #LIST 12 BLOCK CONT SCALE CONT N ( 1 ,X'S,U'S) UNTIL C ( 31 ) CONT H ( 21 ,X'S) UNTIL H ( 311 ) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 25/07/11 at 14:18:25 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ;