# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _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 ? #============================================================================= # 2. 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 ? loop_ _publ_author_name _publ_author_address S.M.Wales ; Department of Chemistry, University of Wollongong, Wollongong, N.S.W. 2522, Australia ; A.C.Willis ; Research School of Chemistry, The Australian National University, Canberra, A.C.T. 0200, Australia ; P.A.Keller ; Department of Chemistry, University of Wollongong, Wollongong, N.S.W. 2522, Australia ; _publ_contact_author_address ; Research School of Chemistry, The Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_author_email willis@rsc.anu.edu.au _publ_contact_author_fax ' 61 2 6125 0750 ' _publ_contact_author_phone ' 61 2 6125 4109 ' _publ_contact_author_name 'Anthony C. Willis' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category FO _publ_requested_coeditor_name ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; The first stereoselective syntheses of 2,2'-biindoline ; data_wol0902a _database_code_depnum_ccdc_archive 'CCDC 794927' #TrackingRef 'wol0902a-wol0903.txt' _audit_creation_date 09-03-05 _audit_creation_method CRYSTALS_ver_12.85 _audit_update_record ; 2009-03-05 - Report on C16 H16 N2 by Anthony C. Willis for Paul Keller 2009-03-05 - passes checkcif tests with minor warnings 2010-09-28 - combine wol0902a and wol0903 for manuscript to Chem Comm Manuscript ID: CC-COM-09-2010-004045 ; _oxford_structure_analysis_title '3051226 wol0902' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 11.6395(4) _cell_length_b 7.8596(3) _cell_length_c 14.2979(6) _cell_angle_alpha 90 _cell_angle_beta 109.257(3) _cell_angle_gamma 90 _cell_volume 1234.81(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-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' _cell_formula_units_Z 4 # Given Formula = C16 H16 N2 # Dc = 1.27 Fooo = 504.00 Mu = 0.76 M = 472.63 # Found Formula = C16 H16 N2 # Dc = 1.27 FOOO = 504.00 Mu = 0.76 M = 472.63 _chemical_formula_sum 'C16 H16 N2' _chemical_formula_moiety 'C16 H16 N2' _chemical_compound_source ' from U of Wollongong' _chemical_formula_weight 236.32 _cell_measurement_reflns_used 53015 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 200 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.37 _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.076 # Sheldrick geometric approximatio 0.99 0.99 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.170 -1 0 0 0.200 0 1 0 0.080 0 -1 0 0.080 0 0 1 0.020 0 0 -1 0.050 6 -5 -3 0.131 -5 -1 2 0.195 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.045 # 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 'Nonius KappaCCD' _diffrn_measurement_device_type 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 1.7 deg at rate 238 sec/frame, crystal-detector distance 28mm, 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, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics ; 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 25324 _reflns_number_total 3033 _diffrn_reflns_av_R_equivalents 0.052 # Number of reflections with Friedels Law is 3033 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2832 _diffrn_reflns_theta_min 2.749 _diffrn_reflns_theta_max 27.482 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.482 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -15 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 3.04 _oxford_diffrn_Wilson_scale 0.87 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.25 _refine_diff_density_max 0.22 # 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 3033 _refine_ls_number_restraints 1 _refine_ls_number_parameters 421 _oxford_refine_ls_R_factor_ref 0.0597 _refine_ls_wR_factor_ref 0.0945 _refine_ls_goodness_of_fit_ref 0.8712 _refine_ls_shift/su_max 0.005551 # The values computed from all data _oxford_reflns_number_all 3033 _refine_ls_R_factor_all 0.0597 _refine_ls_wR_factor_all 0.0945 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2134 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_gt 0.0889 # 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^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~16~H~16~N~2~ is reported. ; _publ_section_comment #Text of the paper ; The crystallographic asymmetric unit consists of two independent C~16~H~16~N~2~ molecules. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; The compound is enantiometrically pure but the 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 those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 \%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 features in the final difference electron density map are located external to the molecules and appear to have no chemical significance. ; _publ_section_exptl_prep ; The compound was recrystallised from methanol/dichloromethane. The sample ID is smw438. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.76128(18) 0.3973(3) 0.28078(16) 0.0396 1.0000 Uani . . . . . . . C2 C 0.8008(2) 0.3985(4) 0.3862(2) 0.0381 1.0000 Uani . . . . . . . C3 C 0.7438(3) 0.4710(4) 0.4478(2) 0.0474 1.0000 Uani . . . . . . . C4 C 0.7988(3) 0.4502(5) 0.5492(2) 0.0548 1.0000 Uani . . . . . . . C5 C 0.9056(3) 0.3599(5) 0.5882(2) 0.0538 1.0000 Uani . . . . . . . C6 C 0.9622(3) 0.2871(4) 0.5251(2) 0.0442 1.0000 Uani . . . . . . . C7 C 0.9091(2) 0.3070(4) 0.42448(19) 0.0389 1.0000 Uani . . . . . . . C8 C 0.9453(2) 0.2442(4) 0.3397(2) 0.0414 1.0000 Uani . . . . . . . C9 C 0.8714(2) 0.3560(4) 0.25294(19) 0.0378 1.0000 Uani . . . . . . . C10 C 0.8415(2) 0.2722(4) 0.15361(19) 0.0379 1.0000 Uani . . . . . . . C11 C 0.9565(2) 0.2213(4) 0.1289(2) 0.0390 1.0000 Uani . . . . . . . C12 C 0.9160(2) 0.2411(3) 0.01828(18) 0.0340 1.0000 Uani . . . . . . . C13 C 0.9695(2) 0.1901(4) -0.0502(2) 0.0389 1.0000 Uani . . . . . . . C14 C 0.9143(2) 0.2313(4) -0.1496(2) 0.0434 1.0000 Uani . . . . . . . C15 C 0.8066(2) 0.3249(4) -0.1788(2) 0.0433 1.0000 Uani . . . . . . . C16 C 0.7519(2) 0.3782(4) -0.1104(2) 0.0390 1.0000 Uani . . . . . . . C17 C 0.8082(2) 0.3363(3) -0.01203(19) 0.0339 1.0000 Uani . . . . . . . N18 N 0.77660(18) 0.3844(3) 0.07049(16) 0.0398 1.0000 Uani . . . . . . . N21 N 0.47174(19) 0.2313(3) 0.18044(16) 0.0389 1.0000 Uani . . . . . . . C22 C 0.4371(2) 0.2390(3) 0.07655(18) 0.0335 1.0000 Uani . . . . . . . C23 C 0.5007(3) 0.1787(4) 0.0164(2) 0.0410 1.0000 Uani . . . . . . . C24 C 0.4475(3) 0.1996(4) -0.0861(2) 0.0440 1.0000 Uani . . . . . . . C25 C 0.3342(2) 0.2739(4) -0.1265(2) 0.0426 1.0000 Uani . . . . . . . C26 C 0.2697(2) 0.3283(3) -0.0651(2) 0.0368 1.0000 Uani . . . . . . . C27 C 0.3226(2) 0.3124(3) 0.03620(18) 0.0321 1.0000 Uani . . . . . . . C28 C 0.2756(2) 0.3579(4) 0.1194(2) 0.0373 1.0000 Uani . . . . . . . C29 C 0.3906(2) 0.3476(4) 0.21167(19) 0.0352 1.0000 Uani . . . . . . . C30 C 0.3643(2) 0.2854(4) 0.30244(18) 0.0351 1.0000 Uani . . . . . . . C31 C 0.2786(2) 0.4049(4) 0.33398(19) 0.0373 1.0000 Uani . . . . . . . C32 C 0.3259(2) 0.3967(4) 0.44522(18) 0.0335 1.0000 Uani . . . . . . . C33 C 0.2763(3) 0.4546(4) 0.5154(2) 0.0423 1.0000 Uani . . . . . . . C34 C 0.3447(3) 0.4344(4) 0.6161(2) 0.0453 1.0000 Uani . . . . . . . C35 C 0.4571(3) 0.3584(4) 0.6441(2) 0.0461 1.0000 Uani . . . . . . . C36 C 0.5083(2) 0.3017(4) 0.57421(19) 0.0402 1.0000 Uani . . . . . . . C37 C 0.4406(2) 0.3210(3) 0.47384(18) 0.0340 1.0000 Uani . . . . . . . N38 N 0.47369(18) 0.2808(3) 0.39152(16) 0.0381 1.0000 Uani . . . . . . . H11 H 0.727(2) 0.498(4) 0.2531(19) 0.0465 1.0000 Uiso . . . . . . . H31 H 0.664(3) 0.534(4) 0.418(2) 0.0569 1.0000 Uiso . . . . . . . H41 H 0.752(3) 0.506(4) 0.592(2) 0.0687 1.0000 Uiso . . . . . . . H51 H 0.940(3) 0.346(4) 0.658(2) 0.0618 1.0000 Uiso . . . . . . . H61 H 1.045(2) 0.221(4) 0.5518(18) 0.0516 1.0000 Uiso . . . . . . . H81 H 0.918(2) 0.132(4) 0.327(2) 0.0488 1.0000 Uiso . . . . . . . H82 H 1.036(2) 0.253(4) 0.3528(18) 0.0490 1.0000 Uiso . . . . . . . H91 H 0.922(2) 0.460(4) 0.2557(18) 0.0434 1.0000 Uiso . . . . . . . H101 H 0.789(2) 0.159(4) 0.1565(18) 0.0435 1.0000 Uiso . . . . . . . H111 H 0.982(2) 0.111(4) 0.154(2) 0.0440 1.0000 Uiso . . . . . . . H112 H 1.024(2) 0.304(3) 0.164(2) 0.0436 1.0000 Uiso . . . . . . . H131 H 1.045(2) 0.127(4) -0.027(2) 0.0464 1.0000 Uiso . . . . . . . H141 H 0.953(2) 0.189(4) -0.2031(19) 0.0499 1.0000 Uiso . . . . . . . H151 H 0.769(2) 0.352(4) -0.252(2) 0.0495 1.0000 Uiso . . . . . . . H161 H 0.674(2) 0.444(4) -0.1338(18) 0.0438 1.0000 Uiso . . . . . . . H181 H 0.699(2) 0.401(4) 0.0639(19) 0.0466 1.0000 Uiso . . . . . . . H211 H 0.555(2) 0.251(4) 0.2140(18) 0.0455 1.0000 Uiso . . . . . . . H231 H 0.583(2) 0.117(4) 0.047(2) 0.0492 1.0000 Uiso . . . . . . . H241 H 0.490(2) 0.165(4) -0.131(2) 0.0563 1.0000 Uiso . . . . . . . H251 H 0.299(2) 0.291(4) -0.201(2) 0.0513 1.0000 Uiso . . . . . . . H261 H 0.192(2) 0.393(4) -0.0913(18) 0.0427 1.0000 Uiso . . . . . . . H281 H 0.215(2) 0.275(4) 0.1290(18) 0.0439 1.0000 Uiso . . . . . . . H282 H 0.237(2) 0.468(4) 0.1111(19) 0.0440 1.0000 Uiso . . . . . . . H291 H 0.431(2) 0.468(4) 0.2312(18) 0.0404 1.0000 Uiso . . . . . . . H301 H 0.332(2) 0.170(4) 0.2905(18) 0.0389 1.0000 Uiso . . . . . . . H311 H 0.186(2) 0.375(4) 0.3053(18) 0.0432 1.0000 Uiso . . . . . . . H312 H 0.284(2) 0.521(4) 0.3084(19) 0.0424 1.0000 Uiso . . . . . . . H331 H 0.197(3) 0.509(4) 0.494(2) 0.0502 1.0000 Uiso . . . . . . . H341 H 0.306(2) 0.482(4) 0.668(2) 0.0541 1.0000 Uiso . . . . . . . H351 H 0.502(2) 0.339(4) 0.719(2) 0.0508 1.0000 Uiso . . . . . . . H361 H 0.586(2) 0.242(4) 0.5911(17) 0.0441 1.0000 Uiso . . . . . . . H381 H 0.522(2) 0.192(4) 0.3929(19) 0.0441 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 0.0369(11) 0.0403(13) 0.0436(13) 0.0058(11) 0.0159(9) 0.0092(10) C2 0.0374(13) 0.0345(15) 0.0455(16) 0.0005(13) 0.0178(11) -0.0058(12) C3 0.0495(16) 0.0417(16) 0.057(2) -0.0072(15) 0.0256(14) -0.0045(14) C4 0.070(2) 0.0498(19) 0.056(2) -0.0125(16) 0.0363(18) -0.0151(17) C5 0.0632(19) 0.057(2) 0.0422(17) -0.0003(16) 0.0187(14) -0.0186(18) C6 0.0494(14) 0.0437(17) 0.0391(16) 0.0036(15) 0.0140(12) -0.0051(15) C7 0.0383(12) 0.0375(16) 0.0429(16) 0.0033(13) 0.0161(11) -0.0023(12) C8 0.0350(13) 0.0456(18) 0.0432(15) 0.0064(14) 0.0126(11) 0.0069(13) C9 0.0374(12) 0.0396(16) 0.0381(15) 0.0017(13) 0.0145(11) 0.0009(13) C10 0.0354(12) 0.0373(15) 0.0411(15) 0.0025(13) 0.0126(10) 0.0026(12) C11 0.0338(13) 0.0396(16) 0.0411(15) 0.0002(13) 0.0089(11) 0.0070(12) C12 0.0303(12) 0.0304(14) 0.0395(14) -0.0021(12) 0.0090(10) -0.0017(11) C13 0.0319(12) 0.0351(15) 0.0492(16) -0.0043(13) 0.0126(11) 0.0002(12) C14 0.0468(15) 0.0416(17) 0.0445(16) -0.0061(13) 0.0188(12) -0.0070(13) C15 0.0473(14) 0.0407(17) 0.0386(15) -0.0006(12) 0.0098(12) -0.0037(13) C16 0.0371(12) 0.0365(15) 0.0400(15) -0.0015(13) 0.0079(11) -0.0008(13) C17 0.0314(11) 0.0290(14) 0.0414(15) -0.0039(12) 0.0119(10) -0.0040(11) N18 0.0342(10) 0.0429(13) 0.0409(13) 0.0006(12) 0.0105(9) 0.0061(11) N21 0.0358(11) 0.0456(14) 0.0359(12) 0.0007(11) 0.0126(9) 0.0044(11) C22 0.0331(12) 0.0302(15) 0.0398(14) 0.0006(12) 0.0153(10) -0.0008(11) C23 0.0416(13) 0.0381(16) 0.0485(18) -0.0024(14) 0.0220(13) -0.0005(13) C24 0.0529(16) 0.0412(16) 0.0478(17) -0.0045(14) 0.0299(14) -0.0041(14) C25 0.0614(17) 0.0340(15) 0.0347(15) 0.0003(13) 0.0190(12) -0.0043(15) C26 0.0383(13) 0.0350(16) 0.0367(15) 0.0008(12) 0.0116(11) -0.0025(12) C27 0.0377(12) 0.0266(15) 0.0356(14) -0.0008(11) 0.0169(11) -0.0028(11) C28 0.0393(13) 0.0415(17) 0.0350(14) 0.0018(13) 0.0174(11) 0.0044(13) C29 0.0354(12) 0.0372(16) 0.0343(14) 0.0007(13) 0.0133(10) -0.0009(12) C30 0.0385(13) 0.0368(15) 0.0297(13) -0.0018(12) 0.0107(10) -0.0024(13) C31 0.0304(12) 0.0462(17) 0.0344(14) -0.0014(13) 0.0093(10) 0.0009(12) C32 0.0327(11) 0.0350(15) 0.0327(13) 0.0003(12) 0.0108(10) -0.0037(11) C33 0.0458(15) 0.0425(16) 0.0414(17) 0.0005(14) 0.0182(13) 0.0017(13) C34 0.0591(17) 0.0429(18) 0.0400(16) -0.0019(13) 0.0247(14) -0.0050(14) C35 0.0578(16) 0.0429(17) 0.0335(15) 0.0011(13) 0.0095(12) -0.0094(15) C36 0.0408(13) 0.0392(17) 0.0355(14) 0.0048(12) 0.0056(11) 0.0034(12) C37 0.0358(12) 0.0334(16) 0.0328(13) 0.0023(11) 0.0113(10) -0.0007(12) N38 0.0356(11) 0.0431(13) 0.0353(12) -0.0008(11) 0.0114(9) 0.0069(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.110(5) 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 . C2 . 1.424(3) yes N1 . C9 . 1.498(3) yes N1 . H11 . 0.92(3) no C2 . C3 . 1.388(4) yes C2 . C7 . 1.396(4) yes C3 . C4 . 1.387(4) yes C3 . H31 . 1.01(3) no C4 . C5 . 1.379(5) yes C4 . H41 . 1.04(3) no C5 . C6 . 1.404(4) yes C5 . H51 . 0.95(3) no C6 . C7 . 1.374(4) yes C6 . H61 . 1.05(3) no C7 . C8 . 1.493(4) yes C8 . C9 . 1.532(4) yes C8 . H81 . 0.93(3) no C8 . H82 . 1.02(3) no C9 . C10 . 1.499(4) yes C9 . H91 . 1.00(3) no C10 . C11 . 1.546(3) yes C10 . N18 . 1.472(4) yes C10 . H101 . 1.09(3) no C11 . C12 . 1.502(4) yes C11 . H111 . 0.95(3) no C11 . H112 . 1.02(3) no C12 . C13 . 1.382(4) yes C12 . C17 . 1.401(3) yes C13 . C14 . 1.392(4) yes C13 . H131 . 0.97(3) no C14 . C15 . 1.394(4) yes C14 . H141 . 1.06(3) no C15 . C16 . 1.395(4) yes C15 . H151 . 1.01(3) no C16 . C17 . 1.381(4) yes C16 . H161 . 1.00(3) no C17 . N18 . 1.399(3) yes N18 . H181 . 0.89(2) no N21 . C22 . 1.406(3) yes N21 . C29 . 1.485(3) yes N21 . H211 . 0.94(2) no C22 . C23 . 1.391(4) yes C22 . C27 . 1.391(3) yes C23 . C24 . 1.400(4) yes C23 . H231 . 1.04(3) no C24 . C25 . 1.382(4) yes C24 . H241 . 0.96(3) no C25 . C26 . 1.397(4) yes C25 . H251 . 1.02(3) no C26 . C27 . 1.380(4) yes C26 . H261 . 0.99(3) no C27 . C28 . 1.507(3) yes C28 . C29 . 1.541(3) yes C28 . H281 . 1.00(3) no C28 . H282 . 0.96(3) no C29 . C30 . 1.510(3) yes C29 . H291 . 1.05(3) no C30 . C31 . 1.541(4) yes C30 . N38 . 1.475(3) yes C30 . H301 . 0.97(3) no C31 . C32 . 1.503(3) yes C31 . H311 . 1.04(2) no C31 . H312 . 0.99(3) no C32 . C33 . 1.390(4) yes C32 . C37 . 1.394(3) yes C33 . C34 . 1.406(4) yes C33 . H331 . 0.97(3) no C34 . C35 . 1.372(4) yes C34 . H341 . 1.05(3) no C35 . C36 . 1.395(4) yes C35 . H351 . 1.04(3) no C36 . C37 . 1.399(4) yes C36 . H361 . 0.98(3) no C37 . N38 . 1.390(3) yes N38 . H381 . 0.89(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C9 . 106.05(19) yes C2 . N1 . H11 . 113.2(17) no C9 . N1 . H11 . 111.3(17) no N1 . C2 . C3 . 128.3(2) yes N1 . C2 . C7 . 110.3(2) yes C3 . C2 . C7 . 121.4(3) yes C2 . C3 . C4 . 117.5(3) yes C2 . C3 . H31 . 120.0(17) no C4 . C3 . H31 . 122.5(17) no C3 . C4 . C5 . 121.8(3) yes C3 . C4 . H41 . 114.5(17) no C5 . C4 . H41 . 123.7(17) no C4 . C5 . C6 . 120.1(3) yes C4 . C5 . H51 . 119.8(19) no C6 . C5 . H51 . 120.1(19) no C5 . C6 . C7 . 118.8(3) yes C5 . C6 . H61 . 122.6(14) no C7 . C6 . H61 . 118.6(14) no C2 . C7 . C6 . 120.3(2) yes C2 . C7 . C8 . 108.2(2) yes C6 . C7 . C8 . 131.5(2) yes C7 . C8 . C9 . 103.5(2) yes C7 . C8 . H81 . 107.6(18) no C9 . C8 . H81 . 108.6(18) no C7 . C8 . H82 . 112.6(15) no C9 . C8 . H82 . 112.5(16) no H81 . C8 . H82 . 112(2) no C8 . C9 . N1 . 102.2(2) yes C8 . C9 . C10 . 114.1(2) yes N1 . C9 . C10 . 113.3(2) yes C8 . C9 . H91 . 105.8(15) no N1 . C9 . H91 . 110.7(15) no C10 . C9 . H91 . 110.3(14) no C9 . C10 . C11 . 112.4(2) yes C9 . C10 . N18 . 113.5(2) yes C11 . C10 . N18 . 102.9(2) yes C9 . C10 . H101 . 106.4(14) no C11 . C10 . H101 . 109.6(13) no N18 . C10 . H101 . 112.1(13) no C10 . C11 . C12 . 102.6(2) yes C10 . C11 . H111 . 109.9(16) no C12 . C11 . H111 . 116.2(16) no C10 . C11 . H112 . 107.6(14) no C12 . C11 . H112 . 112.4(15) no H111 . C11 . H112 . 108(2) no C11 . C12 . C13 . 131.1(2) yes C11 . C12 . C17 . 108.6(2) yes C13 . C12 . C17 . 120.2(2) yes C12 . C13 . C14 . 119.5(2) yes C12 . C13 . H131 . 119.0(16) no C14 . C13 . H131 . 121.5(16) no C13 . C14 . C15 . 119.7(3) yes C13 . C14 . H141 . 120.3(14) no C15 . C14 . H141 . 120.0(14) no C14 . C15 . C16 . 121.5(3) yes C14 . C15 . H151 . 117.4(16) no C16 . C15 . H151 . 121.1(15) no C15 . C16 . C17 . 118.0(3) yes C15 . C16 . H161 . 119.7(14) no C17 . C16 . H161 . 122.3(14) no C12 . C17 . C16 . 121.2(2) yes C12 . C17 . N18 . 109.9(2) yes C16 . C17 . N18 . 128.8(2) yes C10 . N18 . C17 . 108.2(2) yes C10 . N18 . H181 . 114.1(19) no C17 . N18 . H181 . 119.6(17) no C22 . N21 . C29 . 107.57(19) yes C22 . N21 . H211 . 114.9(15) no C29 . N21 . H211 . 113.4(17) no N21 . C22 . C23 . 127.8(2) yes N21 . C22 . C27 . 111.0(2) yes C23 . C22 . C27 . 121.2(2) yes C22 . C23 . C24 . 117.8(3) yes C22 . C23 . H231 . 120.2(15) no C24 . C23 . H231 . 122.0(15) no C23 . C24 . C25 . 121.2(3) yes C23 . C24 . H241 . 121.0(17) no C25 . C24 . H241 . 117.8(17) no C24 . C25 . C26 . 120.2(3) yes C24 . C25 . H251 . 119.3(15) no C26 . C25 . H251 . 120.4(15) no C25 . C26 . C27 . 119.0(2) yes C25 . C26 . H261 . 122.0(15) no C27 . C26 . H261 . 118.5(15) no C22 . C27 . C26 . 120.5(2) yes C22 . C27 . C28 . 108.6(2) yes C26 . C27 . C28 . 130.9(2) yes C27 . C28 . C29 . 102.9(2) yes C27 . C28 . H281 . 114.1(16) no C29 . C28 . H281 . 107.4(14) no C27 . C28 . H282 . 112.9(16) no C29 . C28 . H282 . 112.9(16) no H281 . C28 . H282 . 107(2) no C28 . C29 . N21 . 103.5(2) yes C28 . C29 . C30 . 112.81(19) yes N21 . C29 . C30 . 112.9(2) yes C28 . C29 . H291 . 111.4(14) no N21 . C29 . H291 . 111.4(13) no C30 . C29 . H291 . 105.1(14) no C29 . C30 . C31 . 112.9(2) yes C29 . C30 . N38 . 112.83(19) yes C31 . C30 . N38 . 102.7(2) yes C29 . C30 . H301 . 109.0(15) no C31 . C30 . H301 . 111.7(15) no N38 . C30 . H301 . 107.5(14) no C30 . C31 . C32 . 103.7(2) yes C30 . C31 . H311 . 115.3(15) no C32 . C31 . H311 . 112.1(14) no C30 . C31 . H312 . 109.1(15) no C32 . C31 . H312 . 112.6(15) no H311 . C31 . H312 . 104(2) no C31 . C32 . C33 . 131.0(2) yes C31 . C32 . C37 . 108.1(2) yes C33 . C32 . C37 . 120.9(2) yes C32 . C33 . C34 . 118.2(3) yes C32 . C33 . H331 . 119.4(17) no C34 . C33 . H331 . 122.4(17) no C33 . C34 . C35 . 120.7(3) yes C33 . C34 . H341 . 116.8(15) no C35 . C34 . H341 . 122.4(15) no C34 . C35 . C36 . 121.5(3) yes C34 . C35 . H351 . 118.0(15) no C36 . C35 . H351 . 120.4(15) no C35 . C36 . C37 . 118.1(2) yes C35 . C36 . H361 . 123.9(14) no C37 . C36 . H361 . 117.9(14) no C36 . C37 . C32 . 120.6(2) yes C36 . C37 . N38 . 128.6(2) yes C32 . C37 . N38 . 110.8(2) yes C30 . N38 . C37 . 108.9(2) yes C30 . N38 . H381 . 113.5(17) no C37 . N38 . H381 . 120.6(18) 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 N1 N21 3.454(3) . . no N18 C23 3.448(4) . . no N18 C25 3.515(4) . 2_655 no N18 C26 3.527(3) . 2_655 no N38 C3 3.331(4) . . no N38 C34 3.470(4) . 2_646 no N38 C35 3.493(4) . 2_646 no C5 C8 3.467(5) . 2_756 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 N1 C2 C3 C4 . . . . 177.9(3) no N1 C2 C7 C6 . . . . -178.1(3) no N1 C2 C7 C8 . . . . 1.2(3) no N1 C9 C8 C7 . . . . -28.9(3) no N1 C9 C10 N18 . . . . 67.0(3) no N1 C9 C10 C11 . . . . -176.7(2) no N18 C10 C9 C8 . . . . -176.7(2) no N18 C10 C11 C12 . . . . -25.3(3) no N18 C17 C12 C11 . . . . 1.6(3) no N18 C17 C12 C13 . . . . -175.3(2) no N18 C17 C16 C15 . . . . 175.1(3) no N21 C22 C23 C24 . . . . 179.5(3) no N21 C22 C27 C26 . . . . -178.3(2) no N21 C22 C27 C28 . . . . -0.1(3) no N21 C29 C28 C27 . . . . -23.6(3) no N21 C29 C30 N38 . . . . 64.9(3) no N21 C29 C30 C31 . . . . -179.2(2) no N38 C30 C29 C28 . . . . -178.1(2) no N38 C30 C31 C32 . . . . -22.2(3) no N38 C37 C32 C31 . . . . 0.8(3) no N38 C37 C32 C33 . . . . -177.1(3) no N38 C37 C36 C35 . . . . 177.3(3) no C2 N1 C9 C8 . . . . 30.3(3) no C2 N1 C9 C10 . . . . 153.5(3) no C2 C3 C4 C5 . . . . -0.5(5) no C2 C7 C6 C5 . . . . 0.1(5) no C2 C7 C8 C9 . . . . 17.9(3) no C3 C2 N1 C9 . . . . 161.7(3) no C3 C2 C7 C6 . . . . -0.2(5) no C3 C2 C7 C8 . . . . 179.2(3) no C3 C4 C5 C6 . . . . 0.5(6) no C4 C3 C2 C7 . . . . 0.4(5) no C4 C5 C6 C7 . . . . -0.3(5) no C5 C6 C7 C8 . . . . -179.1(3) no C6 C7 C8 C9 . . . . -162.9(3) no C7 C2 N1 C9 . . . . -20.5(3) no C7 C8 C9 C10 . . . . -151.5(2) no C8 C9 C10 C11 . . . . -60.4(3) no C9 C10 N18 C17 . . . . 149.5(2) no C9 C10 C11 C12 . . . . -147.8(2) no C10 N18 C17 C12 . . . . -19.1(3) no C10 N18 C17 C16 . . . . 164.6(3) no C10 C11 C12 C13 . . . . -168.3(3) no C10 C11 C12 C17 . . . . 15.2(3) no C11 C10 N18 C17 . . . . 27.6(3) no C11 C12 C13 C14 . . . . -177.3(3) no C11 C12 C17 C16 . . . . 178.2(2) no C12 C13 C14 C15 . . . . 0.7(4) no C12 C17 C16 C15 . . . . -0.9(4) no C13 C12 C17 C16 . . . . 1.3(4) no C13 C14 C15 C16 . . . . -0.3(4) no C14 C13 C12 C17 . . . . -1.2(4) no C14 C15 C16 C17 . . . . 0.4(4) no C22 N21 C29 C28 . . . . 24.6(3) no C22 N21 C29 C30 . . . . 146.9(2) no C22 C23 C24 C25 . . . . -1.6(5) no C22 C27 C26 C25 . . . . -1.8(4) no C22 C27 C28 C29 . . . . 15.2(3) no C23 C22 N21 C29 . . . . 166.4(3) no C23 C22 C27 C26 . . . . -0.5(4) no C23 C22 C27 C28 . . . . 177.7(3) no C23 C24 C25 C26 . . . . -0.7(5) no C24 C23 C22 C27 . . . . 2.2(4) no C24 C25 C26 C27 . . . . 2.3(4) no C25 C26 C27 C28 . . . . -179.5(3) no C26 C27 C28 C29 . . . . -166.9(3) no C27 C22 N21 C29 . . . . -16.0(3) no C27 C28 C29 C30 . . . . -145.9(2) no C28 C29 C30 C31 . . . . -62.3(3) no C29 C30 N38 C37 . . . . 145.6(2) no C29 C30 C31 C32 . . . . -144.0(2) no C30 N38 C37 C32 . . . . -16.2(3) no C30 N38 C37 C36 . . . . 166.9(3) no C30 C31 C32 C33 . . . . -168.5(3) no C30 C31 C32 C37 . . . . 13.8(3) no C31 C30 N38 C37 . . . . 23.8(3) no C31 C32 C33 C34 . . . . -177.6(3) no C31 C32 C37 C36 . . . . 178.0(3) no C32 C33 C34 C35 . . . . -0.4(5) no C32 C37 C36 C35 . . . . 0.7(4) no C33 C32 C37 C36 . . . . 0.0(4) no C33 C34 C35 C36 . . . . 1.2(5) no C34 C33 C32 C37 . . . . -0.2(5) no C34 C35 C36 C37 . . . . -1.4(5) no #===END data_wol0903 _database_code_depnum_ccdc_archive 'CCDC 794928' #TrackingRef 'wol0902a-wol0903.txt' _audit_creation_date 09-05-25 _audit_creation_method CRYSTALS_ver_12.85 _audit_update_record ; 2009-05-22 - Report on C16.44 H16.66 Cl2 N2.22 Pd1 by Anthony C. Willis for Paul Keller 2009-05-22 - passes checkcif tests with minor warnings 2009-05-25 - new version to fix poor C-H bonds ; _oxford_structure_analysis_title 'transf axes for std setting of sp gp' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 21.0215(6) _cell_length_b 8.2900(2) _cell_length_c 9.0928(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1584.59(8) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x+1/2,y+1/2,-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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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' Pd -0.9988 1.0072 19.3319 0.6987 15.5017 7.9893 5.2954 25.2052 0.6058 76.8986 5.2659 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C16 H16 Cl2 N2 Pd1 # Dc = 1.73 Fooo = 841.07 Mu = 15.02 M = 413.62 # Found Formula = C16.45 H16 Cl2 N2.22 Pd1 # Dc = 1.77 FOOO = 841.07 Mu = 15.04 M = 422.16 _chemical_formula_sum 'C16.450 H16.675 Cl2 N2.225 Pd1' _chemical_formula_moiety 'C16 H16 Cl2 N2 Pd, 0.225(C2 H3 N)' _chemical_compound_source ' from U of Wollongong' _chemical_formula_weight 422.86 # 422.16 _cell_measurement_reflns_used 21993 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 200 _exptl_crystal_description needle _exptl_crystal_colour brown _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.36 _exptl_crystal_density_diffrn 1.772 # 1.769 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 841.073 _exptl_absorpt_coefficient_mu 1.504 # Sheldrick geometric approximatio 0.79 0.90 # Absorption correction # faces transformed loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.180 0 -1 0 0.180 0 0 1 0.080 0 0 -1 0.080 1 0 0 0.060 -1 0 0 0.010 0 1 -1 0.118 0 -1 1 0.120 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.742 _exptl_absorpt_correction_T_max 0.902 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; # 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 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 1.2 deg at rate 72 sec/frame, crystal-detector distance 40mm, multiple scan sets so over 90 percent of data collected with 2-fold redundancy or more [not assuming Friedel's Law]. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics ; 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 14560 _reflns_number_total 3618 _diffrn_reflns_av_R_equivalents 0.038 # Number of reflections with Friedels Law is 2087 # Number of reflections without Friedels Law is 3618 # Theoretical number of reflections is about 1814 _diffrn_reflns_theta_min 2.641 _diffrn_reflns_theta_max 27.469 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.469 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min -27 _reflns_limit_h_max 27 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 2.30 _oxford_diffrn_Wilson_scale 6.22 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.40 _refine_diff_density_max 0.38 # 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 3618 _refine_ls_number_restraints 18 _refine_ls_number_parameters 225 _oxford_refine_ls_R_factor_ref 0.0267 _refine_ls_wR_factor_ref 0.0507 _refine_ls_goodness_of_fit_ref 0.8545 _refine_ls_shift/su_max 0.028927 # The values computed from all data _oxford_reflns_number_all 3618 _refine_ls_R_factor_all 0.0267 _refine_ls_wR_factor_all 0.0507 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3235 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_gt 0.0490 _refine_ls_abs_structure_Flack -0.02(3) _refine_ls_abs_structure_details 'Flack (1983), 1531 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration rmad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # 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^) + ( 0.00P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of [(C~16~H~16~N~2~)PdCl~2~].0.225CH~3~CN is reported. ; _publ_section_comment #Text of the paper ; The crystallographic asymmetric unit consists of one [(C~16~H~16~N~2~)PdCl~2~] molecule and a disordered acetonitrile molecule of crystallization with occupancy 0.225(4). ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; The compound is enantiometrically pure. The absolute structure of the crystal has been determined by refinement of the Flack parameter and this establishes the absolute configuration of the molecule. It is in agreement with the configuration expected on the basis of the synthetic precursors. Away from the [(C~16~H~16~N~2~)PdCl~2~] molecule there is a region of residual electron density about a crystallographic two-fold axis that appears to be a solvate molecule. This has been modelled as a disordered acetonitrile molecule of crystallization. Restraints were imposed on distances, angles and displacement parameters as the atomic sites overlap with their symmetry-related counterparts. >From its size it was clear that the molecule had less than full occupancy, so this has been included as a refinable parameter. H atoms, excluding those of the acetonitrile, were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 \%A) and with U~iso~(H) in the range 1.2-1.5 times U~eq~ of the parent atom, after which the positions of those attached to N were refined without restraints and those attached to C were refined with riding constraints. Displacement parameters were held fixed. The acetonitrile H atoms were not located. The largest features in the final difference electron density map are located near the Pd atom. ; _publ_section_exptl_prep ; The compound was recrystallised from acetonitrile. The sample ID is smw442. ; _refine_special_details # see also _refine_ls_hydrogen for refinement keywords. ; The compound is enantiometrically pure. The absolute structure of the crystal has been determined by refinement of the Flack parameter and this establishes the absolute configuration of the molecule. It is in agreement with the configuration expected on the basis of the synthetic precursors. Away from the [(C~16~H~16~N~2~)PdCl~2~] molecule there is a region of residual electron density about a crystallographic two-fold axis that appears to be a solvate molecule. This has been modelled as a disordered acetonitrile molecule of crystallization. Restraints were imposed on distances, angles and displacement parameters as the atomic sites overlap with their symmetry-related counterparts. >From its size it was clear that the molecule has less than full occupancy, so this has been included as a refinable parameter. H atoms, excluding those of the acetonitrile, were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 \%A) and with U~iso~(H) in the range 1.2-1.5 times U~eq~ of the parent atom, after which the positions of those attached to N were refined without restraints and those attached to C were refined with riding constraints. Displacement parameters were held fixed. The acetonitrile H atoms were not located. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. 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. Flack, H.D. (1983) Acta Cryst., A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Pd1 Pd 0.291328(9) 0.38821(2) 0.50433(2) 0.0256 1.0000 Uani . . . . . . . Cl1 Cl 0.34667(4) 0.49237(10) 0.70241(8) 0.0379 1.0000 Uani . . . . . . . Cl2 Cl 0.20788(4) 0.31574(9) 0.65395(8) 0.0396 1.0000 Uani . . . . . . . N1 N 0.36153(11) 0.4479(3) 0.3568(3) 0.0272 1.0000 Uani . . . . . . . N18 N 0.24563(10) 0.3017(3) 0.3236(3) 0.0268 1.0000 Uani . . . . . . . N93 N -0.0061(10) -0.116(3) 0.157(2) 0.0913 0.225(4) Uani D U P . . . . C2 C 0.42258(12) 0.3622(3) 0.3541(3) 0.0289 1.0000 Uani . . . . . . . C3 C 0.45722(13) 0.3150(4) 0.4750(4) 0.0372 1.0000 Uani . . . . . . . C4 C 0.51434(15) 0.2366(4) 0.4491(4) 0.0466 1.0000 Uani . . . . . . . C5 C 0.53466(14) 0.2050(4) 0.3069(4) 0.0465 1.0000 Uani . . . . . . . C6 C 0.49904(15) 0.2555(4) 0.1870(4) 0.0428 1.0000 Uani . . . . . . . C7 C 0.44202(12) 0.3359(3) 0.2106(3) 0.0326 1.0000 Uani . . . . . . . C8 C 0.39517(13) 0.4051(4) 0.1040(3) 0.0362 1.0000 Uani . . . . . . . C9 C 0.33610(13) 0.4292(3) 0.2010(3) 0.0271 1.0000 Uani . . . . . . . C10 C 0.29304(13) 0.2813(3) 0.1997(3) 0.0275 1.0000 Uani . . . . . . . C11 C 0.25248(13) 0.2718(4) 0.0589(3) 0.0327 1.0000 Uani . . . . . . . C12 C 0.19461(13) 0.3672(3) 0.1027(3) 0.0291 1.0000 Uani . . . . . . . C13 C 0.14565(13) 0.4274(3) 0.0178(3) 0.0352 1.0000 Uani . . . . . . . C14 C 0.09638(14) 0.5085(4) 0.0856(3) 0.0394 1.0000 Uani . . . . . . . C15 C 0.09587(14) 0.5302(4) 0.2372(4) 0.0409 1.0000 Uani . . . . . . . C16 C 0.14452(13) 0.4707(3) 0.3236(3) 0.0340 1.0000 Uani . . . . . . . C17 C 0.19250(12) 0.3885(3) 0.2546(3) 0.0270 1.0000 Uani . . . . . . . C91 C 0.0274(11) 0.180(3) 0.190(3) 0.1107 0.225(4) Uani D U P . . . 3 C92 C 0.0069(8) 0.014(3) 0.1676(9) 0.0981 0.225(4) Uani D U P . . . . H11 H 0.3623(15) 0.550(4) 0.374(4) 0.0406 1.0000 Uiso . . . . . . . H31 H 0.4429 0.3320 0.5714 0.0452 1.0000 Uiso R . . . . . . H41 H 0.5367 0.2092 0.5228 0.0565 1.0000 Uiso R . . . . . . H51 H 0.5714 0.1456 0.2930 0.0563 1.0000 Uiso R . . . . . . H61 H 0.5137 0.2476 0.0896 0.0508 1.0000 Uiso R . . . . . . H81 H 0.4088 0.5022 0.0651 0.0447 1.0000 Uiso R . . . . . . H82 H 0.3863 0.3340 0.0221 0.0438 1.0000 Uiso R . . . . . . H91 H 0.3125 0.5265 0.1789 0.0319 1.0000 Uiso R . . . . . . H101 H 0.3177 0.1819 0.2189 0.0319 1.0000 Uiso R . . . . . . H111 H 0.2717 0.3142 -0.0257 0.0390 1.0000 Uiso R . . . . . . H112 H 0.2408 0.1602 0.0364 0.0396 1.0000 Uiso R . . . . . . H131 H 0.1461 0.4114 -0.0827 0.0423 1.0000 Uiso R . . . . . . H141 H 0.0640 0.5513 0.0297 0.0472 1.0000 Uiso R . . . . . . H151 H 0.0619 0.5809 0.2798 0.0489 1.0000 Uiso R . . . . . . H161 H 0.1445 0.4885 0.4234 0.0414 1.0000 Uiso R . . . . . . H181 H 0.2307(14) 0.197(4) 0.346(4) 0.0398 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 Pd1 0.02690(9) 0.02797(9) 0.02207(9) 0.00010(10) 0.00035(11) 0.00175(8) Cl1 0.0421(4) 0.0417(4) 0.0300(4) -0.0067(3) -0.0094(3) 0.0070(3) Cl2 0.0394(4) 0.0508(4) 0.0288(3) 0.0021(3) 0.0098(4) -0.0038(4) N1 0.0266(12) 0.0305(12) 0.0247(12) -0.0001(10) 0.0002(10) -0.0012(10) N18 0.0261(12) 0.0300(12) 0.0244(12) 0.0002(10) 0.0000(9) 0.0000(10) N93 0.034(9) 0.182(13) 0.058(8) -0.001(12) -0.001(8) -0.012(17) C2 0.0235(13) 0.0262(14) 0.0370(15) 0.0000(11) 0.0025(11) -0.0031(11) C3 0.0318(14) 0.0412(15) 0.0386(19) 0.0048(14) -0.0007(13) 0.0018(12) C4 0.0310(16) 0.0482(18) 0.061(2) 0.0093(15) -0.0093(15) 0.0037(14) C5 0.0247(15) 0.0424(18) 0.072(3) -0.0050(17) 0.0034(16) 0.0025(13) C6 0.0277(15) 0.0496(18) 0.051(2) -0.0138(16) 0.0060(15) -0.0078(14) C7 0.0236(13) 0.0341(15) 0.0403(16) -0.0050(13) 0.0025(12) -0.0067(12) C8 0.0322(15) 0.0429(18) 0.0336(15) -0.0022(14) 0.0047(12) -0.0092(14) C9 0.0281(14) 0.0290(14) 0.0242(13) 0.0010(10) -0.0017(11) 0.0007(11) C10 0.0243(12) 0.0331(13) 0.0250(12) -0.0020(10) 0.0032(12) 0.0018(12) C11 0.0289(16) 0.0419(17) 0.0274(14) -0.0070(12) -0.0006(11) -0.0039(13) C12 0.0277(14) 0.0293(14) 0.0303(13) 0.0013(12) -0.0001(11) -0.0046(11) C13 0.0327(14) 0.0428(15) 0.0301(16) 0.0023(13) -0.0051(13) -0.0070(11) C14 0.0321(16) 0.0382(16) 0.0478(19) 0.0037(14) -0.0100(13) 0.0013(14) C15 0.0285(15) 0.0401(17) 0.054(2) -0.0040(15) 0.0022(14) 0.0054(13) C16 0.0305(15) 0.0382(16) 0.0333(15) -0.0043(13) 0.0034(13) -0.0003(12) C17 0.0227(13) 0.0310(13) 0.0275(13) 0.0014(12) -0.0001(10) -0.0029(11) C91 0.053(12) 0.2044(10) 0.075(11) -0.005(14) 0.010(10) -0.014(16) C92 0.035(10) 0.194(10) 0.066(7) 0.000(13) 0.010(9) -0.021(18) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4035(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Pd1 . Cl1 . 2.3115(7) yes Pd1 . Cl2 . 2.2998(8) yes Pd1 . N1 . 2.055(2) yes Pd1 . N18 . 2.035(2) yes N1 . C2 . 1.467(3) yes N1 . C9 . 1.522(3) yes N1 . H11 . 0.86(3) no N18 . C10 . 1.513(3) yes N18 . C17 . 1.469(3) yes N18 . H181 . 0.95(3) no N93 . C92 . 1.117(10) yes C2 . C3 . 1.375(4) yes C2 . C7 . 1.385(4) yes C3 . C4 . 1.386(4) yes C3 . H31 . 0.937 no C4 . C5 . 1.387(5) yes C4 . H41 . 0.850 no C5 . C6 . 1.387(5) yes C5 . H51 . 0.925 no C6 . C7 . 1.388(4) yes C6 . H61 . 0.940 no C7 . C8 . 1.497(4) yes C8 . C9 . 1.536(4) yes C8 . H81 . 0.925 no C8 . H82 . 0.968 no C9 . C10 . 1.524(4) yes C9 . H91 . 0.968 no C10 . C11 . 1.541(4) yes C10 . H101 . 0.989 no C11 . C12 . 1.505(4) yes C11 . H111 . 0.938 no C11 . H112 . 0.978 no C12 . C13 . 1.380(4) yes C12 . C17 . 1.394(4) yes C13 . C14 . 1.380(4) yes C13 . H131 . 0.924 no C14 . C15 . 1.389(4) yes C14 . H141 . 0.921 no C15 . C16 . 1.381(4) yes C15 . H151 . 0.914 no C16 . C17 . 1.369(4) yes C16 . H161 . 0.919 no C91 . C92 . 1.452(10) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl1 . Pd1 . Cl2 . 91.18(3) yes Cl1 . Pd1 . N1 . 93.29(7) yes Cl2 . Pd1 . N1 . 175.50(7) yes Cl1 . Pd1 . N18 . 177.29(7) yes Cl2 . Pd1 . N18 . 91.47(7) yes N1 . Pd1 . N18 . 84.06(9) yes Pd1 . N1 . C2 . 121.51(18) yes Pd1 . N1 . C9 . 109.32(16) yes C2 . N1 . C9 . 104.1(2) yes Pd1 . N1 . H11 . 97(2) no C2 . N1 . H11 . 118(2) no C9 . N1 . H11 . 106(2) no Pd1 . N18 . C10 . 109.24(16) yes Pd1 . N18 . C17 . 122.06(18) yes C10 . N18 . C17 . 103.8(2) yes Pd1 . N18 . H181 . 107.8(20) no C10 . N18 . H181 . 106.0(19) no C17 . N18 . H181 . 106.9(19) no N1 . C2 . C3 . 126.0(3) yes N1 . C2 . C7 . 110.5(2) yes C3 . C2 . C7 . 123.5(3) yes C2 . C3 . C4 . 117.2(3) yes C2 . C3 . H31 . 122.3 no C4 . C3 . H31 . 120.6 no C3 . C4 . C5 . 120.9(3) yes C3 . C4 . H41 . 118.1 no C5 . C4 . H41 . 121.0 no C4 . C5 . C6 . 120.6(3) yes C4 . C5 . H51 . 119.0 no C6 . C5 . H51 . 120.3 no C5 . C6 . C7 . 119.3(3) yes C5 . C6 . H61 . 122.8 no C7 . C6 . H61 . 117.6 no C6 . C7 . C2 . 118.5(3) yes C6 . C7 . C8 . 130.7(3) yes C2 . C7 . C8 . 110.8(2) yes C7 . C8 . C9 . 102.1(2) yes C7 . C8 . H81 . 112.2 no C9 . C8 . H81 . 110.9 no C7 . C8 . H82 . 113.1 no C9 . C8 . H82 . 111.4 no H81 . C8 . H82 . 107.3 no C8 . C9 . N1 . 105.3(2) yes C8 . C9 . C10 . 111.8(2) yes N1 . C9 . C10 . 107.3(2) yes C8 . C9 . H91 . 113.8 no N1 . C9 . H91 . 106.8 no C10 . C9 . H91 . 111.4 no C9 . C10 . N18 . 107.2(2) yes C9 . C10 . C11 . 112.1(2) yes N18 . C10 . C11 . 105.1(2) yes C9 . C10 . H101 . 110.9 no N18 . C10 . H101 . 107.9 no C11 . C10 . H101 . 113.2 no C10 . C11 . C12 . 101.5(2) yes C10 . C11 . H111 . 115.1 no C12 . C11 . H111 . 111.6 no C10 . C11 . H112 . 111.2 no C12 . C11 . H112 . 110.4 no H111 . C11 . H112 . 107.0 no C11 . C12 . C13 . 130.2(3) yes C11 . C12 . C17 . 110.8(2) yes C13 . C12 . C17 . 119.0(3) yes C12 . C13 . C14 . 119.1(3) yes C12 . C13 . H131 . 119.6 no C14 . C13 . H131 . 121.3 no C13 . C14 . C15 . 120.8(3) yes C13 . C14 . H141 . 119.7 no C15 . C14 . H141 . 119.5 no C14 . C15 . C16 . 120.8(3) yes C14 . C15 . H151 . 119.1 no C16 . C15 . H151 . 120.0 no C15 . C16 . C17 . 117.6(3) yes C15 . C16 . H161 . 120.2 no C17 . C16 . H161 . 122.2 no N18 . C17 . C12 . 109.7(2) yes N18 . C17 . C16 . 127.5(2) yes C12 . C17 . C16 . 122.7(3) yes C91 . C92 . N93 . 175.3(13) yes #------------------------------------------------------------------------------ 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 Cl1 C91 3.22(2) . 3_556 no Cl1 N18 3.224(2) . 3_556 no Cl1 C92 3.30(2) . 3_556 no Cl1 C17 3.408(3) . 3_556 no Cl1 N93 3.50(2) . 2_556 no Cl1 C92 3.57(2) . 2_556 no Cl2 N1 3.382(3) . 3_546 no Cl2 C9 3.586(3) . 3_546 no N93 C6 3.31(2) . 3_545 no N93 C8 3.33(2) . 3_545 no N93 C3 3.55(2) . 3_546 no C3 C91 3.38(3) . 2_556 no C3 C3 3.556(6) . 4_665 no C4 C91 3.36(3) . 2_556 no C6 C91 3.52(3) . 2 no C8 C92 3.34(1) . 3 no C8 C92 3.47(1) . 2 no C13 C91 3.58(2) . . no C14 C91 3.23(3) . . no C15 C91 3.27(2) . . no C15 C91 3.56(2) . 4_565 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 Pd1 N1 C2 C3 . . . . -41.5(4) no Pd1 N1 C2 C7 . . . . 139.4(2) no Pd1 N1 C9 C8 . . . . -156.8(2) no Pd1 N1 C9 C10 . . . . -37.6(2) no Pd1 N18 C10 C9 . . . . -42.2(2) no Pd1 N18 C10 C11 . . . . -161.7(2) no Pd1 N18 C17 C12 . . . . 144.8(2) no Pd1 N18 C17 C16 . . . . -39.3(4) no Cl1 Pd1 N1 C2 . . . . 71.1(2) no Cl1 Pd1 N1 C9 . . . . -167.9(2) no Cl2 Pd1 N18 C10 . . . . -163.5(2) no Cl2 Pd1 N18 C17 . . . . 75.4(2) no N1 Pd1 N18 C10 . . . . 17.0(2) no N1 Pd1 N18 C17 . . . . -104.0(2) no N1 C2 C3 C4 . . . . -179.3(3) no N1 C2 C7 C6 . . . . -179.8(2) no N1 C2 C7 C8 . . . . 0.8(3) no N1 C9 C8 C7 . . . . 25.6(3) no N1 C9 C10 N18 . . . . 52.1(3) no N1 C9 C10 C11 . . . . 166.8(2) no N18 Pd1 N1 C2 . . . . -109.5(2) no N18 Pd1 N1 C9 . . . . 11.6(2) no N18 C10 C9 C8 . . . . 167.0(2) no N18 C10 C11 C12 . . . . 27.4(3) no N18 C17 C12 C11 . . . . -3.5(3) no N18 C17 C12 C13 . . . . 174.4(2) no N18 C17 C16 C15 . . . . -173.7(3) no C2 N1 C9 C8 . . . . -25.7(3) no C2 N1 C9 C10 . . . . 93.6(2) no C2 C3 C4 C5 . . . . -1.2(5) no C2 C7 C6 C5 . . . . -0.3(4) no C2 C7 C8 C9 . . . . -16.8(3) no C3 C2 N1 C9 . . . . -165.0(3) no C3 C2 C7 C6 . . . . 1.0(4) no C3 C2 C7 C8 . . . . -178.4(3) no C3 C4 C5 C6 . . . . 1.9(5) no C4 C3 C2 C7 . . . . -0.3(4) no C4 C5 C6 C7 . . . . -1.1(5) no C5 C6 C7 C8 . . . . 178.9(3) no C6 C7 C8 C9 . . . . 164.0(3) no C7 C2 N1 C9 . . . . 15.8(3) no C7 C8 C9 C10 . . . . -90.6(3) no C8 C9 C10 C11 . . . . -78.2(3) no C9 C10 N18 C17 . . . . 89.4(2) no C9 C10 C11 C12 . . . . -88.7(3) no C10 N18 C17 C12 . . . . 21.1(3) no C10 N18 C17 C16 . . . . -162.9(3) no C10 C11 C12 C13 . . . . 167.2(3) no C10 C11 C12 C17 . . . . -15.1(3) no C11 C10 N18 C17 . . . . -30.0(3) no C11 C12 C13 C14 . . . . 178.2(3) no C11 C12 C17 C16 . . . . -179.7(2) no C12 C13 C14 C15 . . . . 0.2(4) no C12 C17 C16 C15 . . . . 1.7(4) no C13 C12 C17 C16 . . . . -1.8(4) no C13 C14 C15 C16 . . . . -0.2(5) no C14 C13 C12 C17 . . . . 0.7(4) no C14 C15 C16 C17 . . . . -0.7(4) no #------------------------------------------------------------------------------ #===END # start Validation Reply Form _vrf_PUBL024_GLOBAL ; PROBLEM: The number of authors is greater than 5. RESPONSE: ... Not so - 2 cifs with same 3 authors ; # end Validation Reply Form